Unified Physical Property Estimation Relationships, UPPER

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Authors Lian, Bo

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UNIFIED PHYSICAL PROPERTY ESTIMATION RELATIONSHIPS,

UPPER

Bo Lian

______

A Dissertation Submitted to the Faculty of the

DEPARTMENT OF PHARMACEUTICAL SCIENCES

In Partial Fulfillment of the Requirements

For the Degree of

DOCTOR OF PHILOSOPHY

In the Graduate College

THE UNIVERSITY OF ARIZONA

2013

THE UNIVERSITY OF ARIZONA GRADUATE COLLEGE

As members of the Dissertation Committee, we certify that we have read the dissertation prepared by Bo Lian, titled Unified Physical Property Estimation Relationships, UPPER and recommend that it be accepted as fulfilling the dissertation requirement for the Degree of Doctor of Philosophy.

______Date: (05/16/2013) Samuel H Yalkowsky

______Date: (05/16/2013) Michael Mayersohn

______Date: (05/16/2013) Paul B Myrdal

______Date: (05/16/2013) Edward D French

______Date: (05/16/2013) Theodore J Price

Final approval and acceptance of this dissertation is contingent upon the candidate’s submission of the final copies of the dissertation to the Graduate College.

I hereby certify that I have read this dissertation prepared under my direction and recommend that it be accepted as fulfilling the dissertation requirement.

______Date: (05/16/2013) Dissertation Director: Samuel H Yalkowsky

STATEMENT BY AUTHOR

This dissertation has been submitted in partial fulfillment of the requirements for an advanced degree at the University of Arizona and is deposited in the University Library to be made available to borrowers under rules of the Library.

Brief quotations from this dissertation are allowable without special permission, provided that an accurate acknowledgement of the source is made. Requests for permission for extended quotation from or reproduction of this manuscript in whole or in part may be granted by the head of the major department or the Dean of the Graduate College when in his or her judgment the proposed use of the material is in the interests of scholarship. In all other instances, however, permission must be obtained from the author.

SIGNED: Bo Lian

Table of Contents

LIST OF TABLES ...... 6

LIST OF FIGURES ...... 7

ABSTRACT ...... 8

1. Introduction ...... 9

2. Theoretical Background ...... 11

2.1 The UPPER Scheme ...... 11

2.2 Enthalpic Descriptors ...... 14

2.3 Entropic Descriptors ...... 15

2.3.1 Molecular Symmetry (σ) ...... 16

2.3.2 Molecular Flexibility (φ) ...... 16

2.3.3 Molecular Eccentricity (ε) ...... 17

2.3.4 Intercorrelation of Entropic Descriptors ...... 18

3. DATA AND METHOD ...... 19

4. PHYSICOCHEMICAL PROPERTY ESTIMATION ...... 20

4.1 Entropy of Boiling (∆Sb) ...... 20

4.2 Differential Heat Capacity of Boiling (∆Cpb) ...... 22

4.3 Entropy of Melting (∆Sm) ...... 23

4.4 Differential Heat Capacity of Melting (∆Cpm) ...... 25

4.5 Enthalpy of Boiling (∆Hb) ...... 26

4.5.1 Energy of Vaporization at 298K (∆Ev) ...... 28

Table of Contents---Continued

4.6 Enthalpy of Melting (∆Hm) ...... 28

4.7 Boiling Point (Tb) ...... 31

4.8 Melting Point (Tm) ...... 32

4.9 Heat of Sublimation at 298K (∆Hsub) ...... 34

4.10 Molar Volume (V) ...... 35

4.11 Solubility Parameter (δ) ...... 37

4.12 Fugacity Ratios (CLFR, GLFR) ...... 38

4.12.1 Gas-Liquid Fugacity Ratio (GLFR) ...... 39

4.12.2 Crystal-Liquid Fugacity Ratio (CLFR) ...... 39

4.13 Vapor Pressure (VP) ...... 40

4.14 Activity Coefficient in Octanol (γo) ...... 42

4.15 Activity Coefficient in Water (γw) ...... 43

4.16 Solubility in Octanol (So) ...... 45

4.17 Solubility in Water (Sw) ...... 46

4.18 Air-Octanol Partition Coefficient (Kao) ...... 47

4.19 Air-Water Partition Coefficient (Kaw) ...... 48

4.20 Octanol-Water Partition Coefficient (Kow) ...... 49

5. SUMMARY ...... 51

6. CONCLUSION ...... 54

7. APPENDIX A – SUPPLEMENTARY DATA...... 55

REFERENCES ...... 113

LIST OF TABLES

Table 1. UPPER Properties ...... 12

Table 2. Molecular Descriptors for UPPER ...... 13

Table 3. Environmental designations of UPPER groups ...... 15

Table 4. Inter-correlation matrix for the molecular geometric factors ...... 18

Table 5. Group contribution coefficients for calculation of the enthalpy of boiling ...... 27

Table 6. Group contribution coefficients for calculation of the total enthalpy of melting 30

Table 7. Group contribution coefficients for calculation of molar volume ...... 36

Table 8. Group contribution coefficients for calculation of the activity coefficient in

water ...... 44

Table 9: Summary of UPPER relationships for physicochemical property calculation .. 52

Table 10: Summary of UPPER calculation results ...... 53

LIST OF FIGURES

Figure 1. UPPER (Unified Physical Property Estimation Relationships) Scheme ...... 13

Figure 2. Calculated versus experimental entropy of boiling ...... 21

Figure 3. Calculated versus differential Heat Capacity of boiling ...... 23

Figure 4. Calculated versus experimental total entropy of melting ...... 25

Figure 5. Calculated versus experimental enthalpy of boiling ...... 28

Figure 6. Calculated versus experimental total enthalpy of melting ...... 30

Figure 7. Calculated versus experimental boiling point ...... 32

Figure 8. Calculated versus experimental melting point ...... 33

Figure 9. Calculated versus experimental heat of sublimation ...... 35

Figure 10. Calculated versus experimental molar volume ...... 37

Figure 11. Calculated versus experimental solubility parameter ...... 38

Figure 12. Relationship of a pure crystalline substance to its dispersed states...... 40

Figure 13. Calculated versus experimental vapor pressure ...... 41

Figure 14. Calculated versus experimental activity coefficient in water ...... 44

Figure 15. Calculated versus experimental octanol solubility ...... 45

Figure 16. Calculated versus experimental aqueous solubility ...... 47

Figure 17. Calculated versus experimental Air-Octanol Partition Coefficient ...... 48

Figure 18. Calculated versus experimental Air-Water Partition Coefficient ...... 49

Figure 19. Calculated versus experimental Octanol-Water Partition Coefficient ...... 50

ABSTRACT

The knowledge of physicochemical properties of organic compounds becomes

increasingly important. In this study, we developed UPPER (Unified Physical Property

Estimation Relationships), a comprehensive model for the estimation of 20

physicochemical properties of organic compounds. UPPER is a system of

thermodynamically sound relationships that relate the various phase-transition properties to one another, which includes transition heats, transition entropies, transition temperatures, molar volume, vapor pressure, solubilities and partition coefficients in different solvents and etc. UPPER integrates group contributions with the molecular geometric factors that affect transition entropies. All of the predictions are directly based on molecular structure. As a result, the proposed model provides a simple and accurate prediction of the properties studied. UPPER is designed to predict industrially, environmentally and pharmaceutically relevant physicochemical properties of organic compounds. It also can be an aid for the efficient design and synthesis of compounds with optimal physicochemical properties.

1. Introduction

As the synthesis of new compounds becomes more efficient, the need for knowledge

of their physicochemical properties becomes increasingly important. Since experimental

measurement can be costly and time consuming and cannot be performed on compounds that have not yet been synthesized, good prediction methods can be of great value especially for compounds yet to be synthesized.

A number of techniques are available for the estimation of partition coefficients, solubility, melting points, vapor pressure, and other relevant properties. Unfortunately, many of these methods are not compatible with each other, because they are based upon different models or assumptions for the molecule. It is frequently difficult for a user to work with a number of different estimation techniques, and the data obtained from the various methods are sometimes contradictory. Many of these physicochemical property

estimation methods are summarized by Baum (1); Boethling and Mackay (2); Lyman (3);

Reinhard et al.,(4); Yaws (5). One of the most important developments in the estimation

of physicochemical properties of organic compounds is that of Bondi (6), who proposed a

number of schemes based upon a uniform molecular fragmentation pattern. Joback and

Reid (7) developed a series of equations for the estimation of various physicochemical

properties which are based upon Bondi’s molecular fragmentation scheme. The recent

work of Gani and coworkers is nicely illustrated by Hukkerikar et al. (8) where eighteen

pure component properties are calculated by a set of schemes based upon a single

molecular fragmentation pattern. In each case the calculation of a particular property is

based upon a training set of data for that property.

Unfortunately, these fragmentation schemes or group contributions do not consider those entropic properties of molecules that affect boiling points and melting points, as well as other properties that depend upon transition temperatures, such as solubility and vapor pressure. In addition, these fragmentation schemes cannot distinguish between isomers and they do not consider the interdependencies among the various properties.

Over the past twenty years, this laboratory has studied the role of entropy as a determinant of the melting point of organic compounds. Entropic factors related to molecular geometry have been proved to be important determinants of both boiling and melting temperatures in recent reports (9-21).

In this study, we develop a model for the estimation of 20 important physicochemical properties of organic compounds, UPPER (Unified Physiccal Property Estimation

Relationships), which integrates group contribution with the molecular geometry factors that affect transition entropies. UPPER is a system of thermodynamically sound relationships that relate the various phase-transition properties to one another. All of the predictions are directly based on molecular structure. UPPER is designed to facilitate predicting industrially, environmentally and pharmaceutically relevant physicochemical properties of organic compounds. It also leads to the efficient design and synthesis of compounds with optimal physicochemical properties.

2. Theoretical Background

2.1 The UPPER Scheme

Equations are derived for each property in the UPPER scheme on the basis of the

input descriptors, sound thermodynamic reasoning, and/or reasonable and well accepted

approximations. The twenty properties considered are listed in Table 1 along with their

symbols and units. The interdependencies of the properties are illustrated in the UPPER

scheme in Figure 1. The property numbers in Table 1 correspond to the box numbers in

Figure 1. Each arrow represents an equation for a property in terms of properties or descriptors which appear above it in the figure.

The only input required for the UPPER scheme is the SMILES string for the compound of interest, from which the seven primary descriptors listed in Table 2 are calculated. These appear above the horizontal dotted line in Figure 1. Below the dotted line and above the dashed “V" (including boiling point, melting point, and vapor pressure) are properties of the pure compounds. The remaining seven properties are equilibria that involve the compound in a dispersed state. The properties on the left of the dashed “V” are for octanol as the solvent, and those on the right are for water as the solvent. The partition coefficient in the center describes an equilibrium between solutions of octanol and water.

In Figure 1 rectangles represent additive-constitutive group contribution values and the properties calculated directly from them, and the ovals represent geometric descriptors and the properties that are solely dependent upon geometry. The remainder of

the properties are calculated from a combination of additive and geometric descriptors and are shown in rectangles with rounded corners.

Table 1. UPPER Properties

Sect # Symbol Property Units

1 ∆Sb Entropy of Boiling J/K mol

2 ∆Cpb Differential Heat Capacity of Boiling J/K mol

3 ∆Sm Entropy of Melting J/K mol

4 ∆Cpm Differential Heat Capacity of Melting J/K mol

5 ∆Hb Heat of Boiling kJ/mol

5a ∆Ev Energy of Vaporization kJ/mol

6 ∆Hm Heat of Melting kJ/mol

6a ∆Em Energy of Melting kJ/mol

7 Tb Boiling Point K

8 Tm Melting Point K

9 ∆Hsub Heat of Sublimation kJ/mol 10 V Molar Volume cm3/mol 11 δ Solubility Parameter (J/cm3)1/2 12 FR Fugacity Ratios unitless 13 VP Vapor Pressure log (atm)

14 γo Activity Coefficient in Octanol log (mol/L)

15 γw Activity Coefficient in Water log (mol/L)

16 So Solubility in Octanol log (mol/L)

17 Sw Solubility in Water log (mol/L)

18 Kao Air-Octanol Partition Coefficient unitless

19 Kaw Air-Water Partition Coefficient unitless

20 Kow Octanol-Water Partition Coefficient unitless

Table 2. Molecular Descriptors for UPPER Enthalpic Descriptors Group contribution to the heat of boiling (bi) Group contribution to the heat of melting (mi) Group contribution to the molar volume (vi)

Group contribution to the logarithm of the aqueous activity coefficient (qi)

Entropic Descriptors Molecular symmetry (σ ) Molecular flexibility (ϕ) Molecular eccentricity (ε)

STRUCTURE

vi bi σ, φ, ε mi qi

∆ ∆ ∆ ∆ 10-Vol 5 - Hb 1- Sb 3 - Sm 6- Hm &-∆Ev 2-∆Cpb 4-∆Cpm &- ∆Em

9-∆H 11-δ 7- Tb sub 8 -Tm &- ∆S sub

γ 14- oct 12 - FR 15 - γw

16-Soct 13- VP 17- Sw

18-Kao 19 -Kaw

20-K ow

Figure 1. UPPER (Unified Physicochemical Property Estimation Relationships) Scheme

2.2 Enthalpic Descriptors

UPPER treats the properties in Table 2, which reflect enthalpic interactions as

additive constitutive properties that have the general form

P molec = ∑ ni pi (1)

where Pmolec is the property of the whole molecule, the pi are the contributions of

molecular fragments or groups to the property, and ni is the number of pi fragments in the

molecule. UPPER utilizes four sets of additive constitutive parameters: heat of boiling,

heat of melting, molar volume, and aqueous activity coefficient.

Each additive-constitutive molecular fragment in the UPPER scheme is defined as the

smallest group of atoms (consisting of all carbons, hydrogens, and hetero atoms,

including their non-bonded electrons) that are not separated by an isolating carbon. An

isolating carbon was defined by Leo (22) as a carbon atom that is not doubly or triply bonded to a hetero atom.

Each fragment, i, is described by its chemical formula and by its environment. The chemical formula is written in the traditional manner with "=" and "≡" representing double and triple bonds, respectively. This is preceded by an environmental descriptor which is related to the hybrid state of the group’s isolating carbon and whether or not it is in a ring or a bridgehead. These are described in Table 3. (Additional molecular environmental descriptors can be added if necessary)

Table 3. Environmental designations of UPPER groups

Designation Description X group is bonded to a simple aliphatic sp3 carbon and/or hydrogen atoms Y group is bonded to one aromatic or olefinic sp2 carbon and/or hydrogen atoms Z group is bonded to a sp carbon and/or hydrogen atoms YY group is bonded to two sp2 carbons and/or hydrogen atoms FU designates an atom or group contained in two saturated rings RG designates an atom or group in a saturated ring AR designates an atom or group within an aromatic ring system AR2 designates a bridgehead atom contained in two unsaturated rings AR3 designates a bridgehead atom or group contained in three unsaturated rings BIP designates a central atom in a biphenyl type structure

The coefficients for some molecular fragments are influenced by neighboring groups, as

well as the overall molecular shape. These fragments require additional secondary or

proximity descriptors which are combined with the primary group descriptors described

above. This enables a more accurate estimation of molecular properties. Chain coiling

and alignment descriptors along with ring descriptors are used in this study when

necessary.

2.3 Entropic Descriptors

The key to the success of the UPPER scheme is the use of non-additive, whole

molecule, descriptors that relate to entropy. These holistic descriptors are based on

molecular geometry and they are related to the probabilities of the existence of the final

and the initial states of a phase transition. According to Bondi (6), the total entropy can be partitioned into the sum of its rotational, conformational and translational components.

∆S = ∆S rot + ∆S conf + ∆S trans (2) tr tr tr tr

These contributions to the total entropy of transition are in turn related to the

geometric molecular descriptors described below.

2.3.1 Molecular Symmetry (σ)

The external rotational symmetry number (σ) is equal to the orientational degeneracy

of the molecule, i.e. the number of orientations that are identical to a reference

orientation. In UPPER: (1) Hydrogen atoms are assumed to be capable of free and rapid

rotation about the atoms to which they are bonded. Consequently CH3, NH2, and OH are

treated as radially symmetrical groups. (2) Carboxylic acid and nitro groups are treated as

having bilateral symmetry about the bond joining them to the isolating carbon. (3)

Molecules that have infinite symmetry, e.g., spherical (CH4) cylindrical (C2H6) and

conical (CH3Br) are empirically assigned an effective symmetry number of 20. (4) All flexible molecules are assigned a symmetry number of unity.

The rotational entropy of transition is related to the rotational freedom before and

after the transition (9-11). It is given by

rot ∆Str = Atr log σ (3)

were Atr is a constant which is dependent on the nature of the transition.

2.3.2 Molecular Flexibility (φ)

The molecular flexibility number, φ, is a measure of the conformational freedom of

the molecule. The higher the number of conformations possible for a molecule, the

greater is its flexibility. In UPPER, φ is calculated by the following equation.

φ = LIN + 0.5(BR + SP2 + RING) -1 + 0.3 ROT* (4)

where BR = ∑ Non-ring, branched sp3 atoms (CH, C, and N) 3 LIN = ∑ Non-ring, linear sp atoms (CH2, NH, and O) ROT = (LIN – 4) the extra entropy produced by freely rotating linear chain sp3 atoms. SP2 = ∑ Non-ring =CH, =C, =N) RING = ∑ independent single, fused, or conjugated rings, whether aromatic, aliphatic, or alkaryl. * This is used for fusion entropy only

The conformational entropy of transition is given by

∆ conf = φ Str Btr (5)

where Btr is a constant.

2.3.3 Molecular Eccentricity (ε)

Flat or elongated molecules tend to be partially ordered in the liquid. They also

tend to pack more efficiently in the crystal. Packing efficiency determines the

magnitude of the expansion that occurs upon melting. UPPER divides eccentricity into

separate contributions from the number of atoms in the aliphatic rings, εal, and the

number of atoms in the aromatic rings, εar (9, 10). All non-ring compounds are given a minimum eccentricity value of unity. Therefore, the positional entropy is given by

pos ∆Str = Ctr log ε ar + Dtr log ε al (6)

where Ctr and Dtr are regression determined constants.

2.3.4 Intercorrelation of Entropic Descriptors

The above descriptors have very low inter-correlation between them which verifies their mutual independence. This is evidenced by the low values of the squared pair-wise correlation coefficients given in Table 4.

Table 4. Inter-correlation matrix for the molecular geometric factors

logσ φ logεar log εal logσ 1.00 φ 0.03 1.00 logεar 0.05 0.05 1.00 logεal 0.01 0.03 0.03 1.00

3. DATA AND METHOD

A data set of 668 hydrocarbons was included for the evaluation of the 20 properties in the UPPER scheme. This compilation contains a variety of structurally diverse hydrocarbons including linear or branched alkanes, alkenes, alkynes, cycloaliphatics, alkyl aromatics, poly aromatics, etc. These hydrocarbons represent the backbones of organic compounds and cover a wide range of molecular shape and size. The experimentally measured property values were taken from the NIST, Aquasol, Merck

Index (23), EPA database and other references (5, 23-30). All properties were measured at 298K except for the transition properties. The group contribution values of the four enthalpic descriptors and the coefficients of the three entropic descriptors are obtained by

Multiple Linear Regression (MLR) analyses using IBM SPSS (20.0). All of the other values below the horizontal dashed line in Figure 1 are calculated directly from the thermodynamic equations, without any regression. Established alternative descriptors were tested for comparison with the entropic descriptors. Matlab (The Mathworks Inc.

Natick, MA) was used to get the dimensions of the minimum bounding box that enclosed the calculated surface. JOELib was used to find rotational bond counts.

4. PHYSICOCHEMICAL PROPERTY ESTIMATION

The following sections describe the calculation of each of the UPPER properties. The

sub-section numbers correspond to the numbers in Table 1 and Figure 1. Note that each

property is predicted only from the properties that precede it in Table 1 and Figure 1.

4.1 Entropy of Boiling (∆Sb)

The molar entropy of boiling, ∆Sb, is proportional to the logarithm of the ratio of the

probability of existence as a gas, PG, to that of as a liquid, PL,

PG ∆S = R ln (7) b P L

(Note that the probability ratio is not a probability.)

The major difference between the liquid and the gas is free volume. Therefore, the

translational probability ratio is roughly equal to the ratio of the gas to liquid free

volumes. The approximately constant gas/liquid free volume ratio is responsible for the

success of Trouton’s rule which is given by

trans ∆Sb = 88 J/K ⋅ mol (8)

for most liquids. Significant structure-dependent deviations from Trouton’s Rule have been noted. To account for those deviations, the following equation for the prediction of

entropy of boiling was statistically generated.

ΔSb = 83.78 + 1.29logσ + 0.6φ + 5.76logεar + 1.21logεal (9)

where the geometric terms, σ, φ, εar and εal have been described in Section 2.3. above.

The average absolute error (AAE) of 1.14 J/K·mol is low compared to the magnitude of the observed values (80.5-95.8 J/K·mol). Although the values do not deviate greatly from the constant value from Trouton’s Rule, they are better described by the above equation (R2=0.68) than by a constant (Figure 2). In other words, they are closer to the diagonal line of identity than to any horizontal line.

105

b Calc ΔS

75 75 85 95 105 Exp ΔSb

Figure 2. Calculated versus experimental entropy of boiling (---): Trouton’s Rule; (——): Line of identity; N=470

4.2 Differential Heat Capacity of Boiling (∆Cpb)

The heat capacity of a phase is the rate of increase in its enthalpy with temperature over the temperature range of interest. It is expressed in the same units as entropy

(J/K·mol). The differential gas-liquid heat capacity, or the heat capacity of boiling, ∆Cpb, is the difference between the heat capacity of the gaseous and the liquid forms of a substance extrapolated to the boiling point.

According to Sidgwick’s rule, ∆Cpb is constant at -54.4 J/K.mol. Others have proposed that ∆Cpb is related to ∆Sb by a proportionality constant. In general, the values of ∆Cpb range from -0.6 ∆Sb for small nonpolar molecules to -1.0*∆Sb for polar molecules. The following equation has been statistically generated based on the observed

ΔCpb values at 298K.

∆Cpb = −51.7 +14.23 logσ − 5.0 φ − 8.29 logε ar − 9.58 logε al (10)

Equation 10 provides a good estimate of the differential gas-liquid heat capacity for the hydrocarbons (AAE=5.46 J/K mol, R2=0.83) as shown in Figure 3. It is clear that the majority of the values are close to the line of identity. Just like ΔSb, ΔCpb is better estimated by the above equation than using the Sidgwick constant.

-40

-80 CalcΔCp

-120

-160 -160 -120 -80 -40 0 Exp ΔCpb

Figure 3. Calculated versus differential Heat Capacity of boiling (---): Sidgwick’s rule; (——): Line of identity; N=182

4.3 Entropy of Melting (∆Sm)

The total phase change entropy of melting ∆Sm is the entropy difference between the most stable crystal form and the isotropic liquid. As in the case of the entropy of boiling, the entropy of melting is related to the logarithm of the ratio of probabilities of existence of the two phases (or the probability ratio of melting) by:

P L ∆S = R ln (11) m P S

Walden’s rule, which is analogous to the Trouton’s rule, states that the entropy of melting has a constant value of 57 J/K.mol for coal tar derivatives (which are largely aromatic compounds with little or no flexibility).

ΔSm = 57 J/K mol (12)

Like the entropy of boiling, the total entropy of melting can be partitioned into the sum of

its rotational, conformational and translational components.

∆ = ∆ rot + ∆ conf + ∆ trans S m S m S m S m (13)

The following equation for estimating the total entropy of melting was statistically

generated by MLR:

∆S = 43.54 − 8.95 log σ + 8.02 φ + 9.16 log ε + 9.43 log ε (14) m ar al

Figure 4 illustrates the prediction results for ∆Sm. The success of Equation 14 is proven

by the closeness of the calculated melting entropies to the line of identity versus the

observed values (R2=0.98). The average absolute error of 7.06 J/K·mole is low compared

to the average magnitude of the observed values. In contrast, Walden’s Rule (Equation

12, dashed line) does not accurately approximate ∆Sm of compounds with complicated

geometric structures like long chain or poly-ring system. Interestingly, the alternative descriptors based upon molecular dimensions did not provide better fit than the simple descriptors in Equation 14. As a result, ∆Sm was accurately estimated by using 4 simple,

intuitive and non-redundant parameters.

500

400

m 300

Calc ΔS 200

100

0 0 100 200 300 400 500 Exp ΔSm Figure 4. Calculated versus experimental total entropy of melting (---): Walden’s Rule; (——): Line of identity; N=352

4.4 Differential Heat Capacity of Melting (∆Cpm)

The differential heat capacity of melting is defined as the difference between the heat capacities of the isotropic liquid and the most stable solid and extrapolated to the melting point. Two alternative assumptions are commonly used to approximate the differential heat capacity of melting. Many researchers assume that it is equal to zero,

∆Cp = 0 m (15)

While others assume that it is closer to the entropy of melting than to zero, i.e.,

∆Cp = ∆S m m (16)

Mishra and Yalkowsky (21) and Grant, Mehdizadeh (31) demonstrated that the difference between these two approximations does not usually lead to significant difference in the

calculation of molecular properties. UPPER assumes the differential heat capacity of

melting as zero (Equation 15) for mathematical convenience.

4.5 Enthalpy of Boiling (∆Hb)

The enthalpy of boiling, i.e., the enthalpy of vaporization at boiling point, is the heat

required to completely overcome all of the intermolecular interactions between

neighboring molecules for one mole of liquid at the boiling temperature. The total

intermolecular interaction energy is the sum of all of the pair-wise group interactions.

Therefore, the enthalpy of boiling is a constitutive and additive property that can be

approximated by,

∆H = ∑ n b b i i (17)

where ni is the occurrence of the group i and bi is the contribution of that group to the total enthalpy of boiling. An additional bi value of -0.024 kJ/mole is assigned for the

square of the number of unrestricted methylene (X-CH2) groups in the molecule to

account for the coiling of long alkyl chains in the liquid phase, which tends to reduce

their external surface area and thus their contact with neighboring molecules.

Multiple linear regression (MLR) using Equation 17 was performed to generate a coefficient of each group from the observed ∆Hb values (Table 5). Figure 5 shows the

observed versus the estimated ΔHb values for all the compounds studied. The proposed

group contribution scheme provides excellent estimations of the enthalpy of boiling of

the hydrocarbons studied. The R2 is 0.99 and the average absolute error (AAE) is 0.61

kJ/mole, which is negligible compared to the 18.4-74.3 kJ/mole range of the observed values.

Table 5. Group contribution coefficients (kJ/mole) for calculation of the enthalpy of boiling Groups Environmental Descriptor X Y Z YY RG FU AR BR2 BR3 BIP −CH3 9.647 8.255 7.287 ------−CH2 2.554/-0.024* 1.026 0 0.728 2.926 ------−CH -5.277 -7.108 -- -12.965 -4.982 2.116 4.713 ------−C -13.649 -14.939 -- -- -13.192 2.068 -0.305 1.417 2.115 -1.631 =CH2 8.925 ------=CH 3.694 2.866 -- -- 3.141 ------=C -2.109 -2.814 -- -- -3.209 ------≡CH 9.140 ------≡C 6.185 ------=C= 3.590 ------RING ------12.227 -- 1.222 ------

* (X−CH2)2

40 Calc ΔH

0 0 20 40 60 80 Exp ΔHb

Figure 5. Calculated versus experimental enthalpy of boiling (——): Line of identity; N=470

4.5.1 Energy of Vaporization at 298K (∆Ev)

The energy of vaporization (∆Ev) at 298K is related to the enthalpy of boiling at the normal boiling point by

∆E = ∆H − RT − ∆Cp (T − T ) (18) v b b b

4.6 Enthalpy of Melting (∆Hm)

The total molar enthalpy or heat of melting is the heat required to melt one mole of a

solid from its most stable form to the isotropic liquid. The value of ∆Hm is calculated

analogously to heat of boiling by

∆ = H m ∑ nimi (20)

where ni is the occurrence of the group i and mi is the contribution of group i to the total melting enthalpy. For compounds with alkyl chains, the freely rotating or unrestricted methylene (X-CH2) groups tend to have a higher contribution to ∆Hm when the alkyl chain length exceeds 4 methylene groups. This behavior may be due to the fact that long alkyl chains tend to be fully aligned with each other in the solid phase and thus their contact with neighboring molecules increases. As seen is Table 6, the term (X-CH2*) is used to account for this effect.

Table 6. Group contribution coefficients (kJ/mole) for calculation of the total enthalpy of melting Groups Environmental Descriptor X Y Z YY RG FU AR BR2 BR3 BIP −CH3 1.183 1.785 0 ------−CH2 1.906a 0.684 -2.928 1.405 1.319 ------−CH2* 4.000b ------−CH 1.047 -1.545 -- 0.084 0.836 1.127 1.387 ------−C -0.085 -2.246 -- -- -0.519 1.152 1.219 1.478 -1.374 3.123 =CH2 1.371 ------=CH 1.667 1.399 -- -- 0.973 ------=C 1.296 -1.005 -- -- 0.531 ------≡CH 3.150 ------≡C 4.625 ------=C= 1.478 ------RING ------0 -- 0 ------a. The value for the first 4 (X-CH2)s in the molecule b. The value for (X-CH2*)s for the 5th and above

200 180 160 140 120

m 100 80 Calc ΔH 60 40 20 0 0 20 40 60 80 100 120 140 160 180 200 Exp ΔHm

Figure 6. Calculated versus experimental total enthalpy of melting (——): Line of identity; N=352

The group (mi) values generated for calculating the total enthalpy of melting are listed in

Table5. Figure 6 shows the observed ΔHm values fall close to the line of identity with the values calculated by Equation 1. The R2 is 0.99 and the average absolute error (AAE) is

1.80 kJ/mole, which is small compared to the (2.86-185) kJ/mole range of the experimental values.

4.7 Boiling Point (Tb)

Group contribution schemes have largely been used for the estimation of Tb. Many of these have been reviewed by Boethling, Howard (32). By considering the effects of entropy, UPPER provides a more accurate calculation of the boiling point than simple group contribution approaches. Since the free energy of boiling at the boiling point is equal to zero, the Kelvin boiling point, Tb, can easily be calculated from

∆H T = b (21) b ∆ S b where ∆Hb, and ∆Sb, are described in Sections 4.5 and 4.1 respectively.

900

700

500 Calc T

300

100 100 300 500 700 900 Exp Tb Figure 7. Calculated versus experimental boiling point (——): Line of identity; N= 537

The predictions can be seen from Figure 7 to be in excellent agreement with the experimental values. It is significant that the calculated values are based only upon equations for entropy and enthalpy and not trained on boiling point data. This method gives relatively good predictions considering the range of the experimental values (225-

809K). The R2 is 0.99 and AAE is 7.27K.

4.8 Melting Point (Tm)

The melting point is the key parameter in the UPPER scheme. It is required for the calculation of any equilibrium property that involves a crystalline compound, including the vapor pressure of solids and their solubilities in aqueous or organic solvents.

Although melting point is the most commonly reported property of organic compounds and is often the first property measured after a new compound is synthesized, it is one of the most difficult physicochemical properties to predict. A large number of approaches to predict melting point have been proposed. However, most of these are restricted to small datasets of closely related compounds.

At the melting point, the free energy of melting is equal to zero. Thus, the Kelvin melting point, Tm, can be approximated as the ratio of the total enthalpy of melting,

∆Hm, to the total entropy of melting, ∆Sm, which are described in sections 4.6 and 4.3, respectively

∆H m Tm = (22) ∆S m

800

600

m 400 Calc T

200

0 0 200 400 600 800 Exp Tm Figure 8. Calculated versus experimental melting point (——): Line of identity; N= 561

The predictions can be seen from Figure 8 to be in good agreement with the experimental

values through the line of identity. It is significant that the calculated values are based

only upon equations for melting enthalpy and entropy and not trained on any melting

point data. This method gives relatively strong predictions considering the range of the

experimental values (85.5-637.2 K). The R2 is 0.90 and AAE is 23.47 K. This is

satisfactory considering the variety of compounds and the data range.

4.9 Heat of Sublimation at 298K (∆Hsub)

Sublimation is the conversion of a solid to a gas without passing through the liquid phase. The sublimation of a crystalline material can be thought of as hypothetical melting followed by the hypothetical evaporation of the resulting liquid at the same constant

temperature. The heat of sublimation is normally determined at 1 atmosphere and 298K.,

It can be approximated by the sum of the heat of melting and the heat of vaporization at

298K, ∆Hv, as described in Sections 4.6 and 4.5.1, respectively, i.e.,

298 ∆H sub ≈ ∆H m + ∆H v (23)

The predicted heats of sublimation obtained from equation 23 versus the observed values

are shown in Figure 9. Neither regression nor observed data is used to obtain the predicted values. Predictions are in good agreement with the experimentally determined

values with an AAE of 6.23 kJ/mol and R2 of 0.96.

200

sub H ∆ 100 Calc

0 0 100 200 ∆ Exp Hsub Figure 9. Calculated versus experimental heat of sublimation (——): Line of identity; N=66

4.10 Molar Volume (V)

The molar volume of an organic liquid is determined from the ratio of its molecular

weights to its density. In UPPER the molar volume, V, is calculated by the same group

contribution scheme that is used to calculate the heats of boiling and melting,

V = ∑ nivi (24)

where vi is the contribution of that group i to the total molar volume.

The vi values which were obtained by MLR are given in Table 7. The relationship

between the observed and regression-generated values of the molar volume are shown in

Figure 10. Equation 24 provides excellent estimations of the molar volume of the hydrocarbons studied (R2=1.00). The average absolute error, 1.27 cm3/mol, is negligible

compared to the range of the observed values, which extend from 78.3 cm3/mol to 336.5 cm3/mol.

Table 7. Group contribution coefficients (cm3/mole) for calculation of molar volume Group Environmental Descriptor X Y Z YY RG FU AR BR2 BR3 BIP −CH3 32.616 32.783 14.69 ------−CH2 16.271 17.030 0 17.051 13.959 ------−CH -0.933 1.340 -- 2.072 -16.077 9.354 15.275 ------−C -18.485 -14.562 -- -- -5.218 -0.659 -2.586 1.844 0 -0.550 =CH2 30.439 ------=CH 12.564 11.967 -- -- 10.781 ------=C -6.073 -4.828 -- -- 10.776 ------≡CH 25.367 ------≡C 24.420 ------=C= 19.940 ------RING ------24.808 -- 0 ------

500

400

300

Calc V 200

100

0 0 100 200 300 400 500 Exp V Figure 10. Calculated versus experimental molar volume (——): Line of identity; N= 312

4.11 Solubility Parameter (δ)

The solubility parameter (δ) was first defined by Hildebrand and Scott (33) as the square root of the cohesive energy density. It is a measure of the affinity of organic compounds for each other. δ, in (J/cm3)0.5, is calculated by

∆ δ = Ev (25) V

where ∆Ev and V are described in Sections 4.5.1 and 4.10, respectively.

UPPER utilizes the energy of vaporization described by equation 18, and the molar

volume described in equation 24 to calculate the solubility parameter. The available

hydrocarbon solubility parameters are well predicted and plotted against their calculated

values in Figure 11 (AAE=0.21 (J/cm3)1/2 , R2 =0.96). Since the only intermolecular interactions of the hydrocarbons are dispersion forces, their solubility parameters are only minimally dependent upon structure. This is evident in Figure 11.

17 Calc

12 12 17 22 Exp δ

Figure 11. Calculated versus experimental solubility parameter (——): Line of identity; N= 163

4.12 Fugacity Ratios (CLFR, GLFR)

The fugacity ratio is a measure of a tendency of a molecule to exist in one phase over another. Phases that are in equilibrium will have identical fugacities. Fugacity ratios are important in determining equilibria among phases, including solubilities in octanol, water, and air (vapor pressure), as well as partitioning between air and octanol, air and water and octanol and water. Figure 12 shows the interrelationship of these thermodynamic properties and their dependency on fugacity ratios.

The liquid is used as a reference state. Therefore, the gas-liquid fugacity ratio (GLFR) is the ratio of the gas to liquid fugacities, and the crystal-liquid fugacity ratio (CLFR) is the ratio of the fugacity of the crystal to that of the liquid. Note that fugacity ratios are calculated but are not experimentally measured.

4.12.1 Gas-Liquid Fugacity Ratio (GLFR)

The gas-liquid fugacity ratio (GLFR) is the ratio of the thermodynamic activities of a

substance as a gas compared to that of the same substance as a liquid at the same

temperature and pressure. Mathematically, it is described by the integrated form of the

Clausius-Clapeyron equation as

∆S (T −T ) ∆Cp (T −T ) ∆Cp T logGLFR = b b − b b + b log b (26) 2.303RT 2.303RT R T

where ∆Sb ,∆Cpb and Tb are described in Sections 41, 4.2 and 4.7 respectively.

4.12.2 Crystal-Liquid Fugacity Ratio (CLFR)

Likewise, the crystal-liquid solubility ratio is given by

∆S (T −T) ∆Cp (T −T) ∆Cp T logCLFR = − m m + m m − m log m (27) 2.303RT 2.303RT R T

where ∆Sm ,∆Cpm and Tm are described in Sections 4.3, 4.4 and 4.8 respectively.

Since ∆Cpm is assumed to be zero, the above equation simplifies to

∆S (T − T ) log CLFR = − m m (28) 2.303 R T

CLFR - GLFR

Kao Kaw

Pure Crystal

CLFR CLFR γ γ + o + w

So Kow Sw

Figure 12. Relationship of a pure crystalline substance to its dispersed states.

4.13 Vapor Pressure (VP)

The vapor pressure of a pure substance at a given temperature is the pressure exerted by its vapor on its surroundings when it is in equilibrium with its pure liquid or pure solid form. The vapor pressure of a solid is calculated from the integrated forms of the

Clausius-Clapeyron and van’t Hoff equations (34); it is identical to its crystal-gas fugacity ratio as given by

= = − (29) logVP logCGFR logCLFR logGLFR

When Equations 26 and 28 are incorporated, Equation 29 becomes

∆S (T −T ) ∆S (T −T ) ∆Cp (T −T ) ∆Cp T logVP = − m m − b b + b b − b log b (30) 2.303RT 2.303RT 2.303RT R T

where ∆Sb ,∆Cpb , Tb, ∆Sm and Tm are alldescribed by equations given above. For liquids,

Equation 30 is further simplified to

Liq ∆S b (Tb − T ) ∆Cpb (Tb − T ) ∆Cpb Tb logVP = − log GLFR = − + − log (31) 2.303RT 2.303RT R T

The observed and predicted vapor pressures of 335 hydrocarbons are shown in Figure 13.

Clearly, the data (which range over 13 orders of magnitude) fall close to the line of

identity. The AAE is only 0.16 and the R2 is 0.99, which is quite satisfactory considering

the range of data. As in the case of the boiling point, melting point, and heat of

sublimation, vapor pressures were not generated by regression or use of a training set.

Therefore, the values on the y-axis are truly predicted values.

-4 Calc logVP

-8

-12 -12 -8 -4 0 Exp logVP Figure 13. Calculated versus experimental vapor pressure (——): Line of identity; N=335

4.14 Activity Coefficient in Octanol (γo)

Octanol is a poorly water-soluble liquid with low polarity that is often used as a

surrogate for biological lipids and membranes. It forms regular solutions with nonpolar

and semipolar liquids but not with strongly polar, hydrogen bonding liquids. Hildebrand,

Prausnitz (35) defined a regular solution as one in which the entropy of mixing is ideal,

the volume change on mixing is zero, and the enthalpy of mixing is positive.

The activity coefficient of a solute in octanol, γoct, is defined as

α γ oct = u (32) u oct Cu where α is the thermodynamic activity of the solute, u, and C is its concentration. If the

solution is saturated, the activity of the solute, α, is equal to that of the pure solvent,

which is equal to unity. Thus, for liquid solutes the molar activity coefficient is simply

the reciprocal of the molar solubility, i.e., for a saturated solution

1 γ oct = oct (33) Su

According to Scatchard-Hildebrand equation, γo is caluculated by

V (δ − δ ) 2 φ 2 γ = u oct u oct (34) oct 2.3RT where Vu and δu are the molar volume and solubility parameter of the solute calculated

by Equation 24 and 25, respectively. δoct and ϕoct are the solubility parameter and

volume fraction of the solvent, octanol. respectively.

4.15 Activity Coefficient in Water (γw)

The molar activity coefficient of a solute in water is calculated by the same group

contribution scheme that was used above for ∆Hb, ∆Hm and V.

log γ = n q w ∑ i i (35)

where ni is the occurrence of the group i in the molecule and qi is the contribution of that

group to the total activity coefficient. Note that all of the group contribution (bi, mi, vi and

qi) values are based upon experimental data and the same fragmentation pattern.

For liquids, aqueous activity coefficients were generated directly from measured

aqueous solubility values. For crystalline compounds, they were generated by subtracting

the crystal-liquid fugacity ratios from the measured solubility values. The qi values in

Table 8 were obtained by MLR. The relationship between the observed and regression generated values of the aqueous activity coefficient are shown in Figure 14. As can be seen from the figure the above equation provides excellent logγw estimations of the compounds studied (R2=0.93). The average absolute error of 0.26 is small compared to

the observed values which range over 8 orders of magnitude.

Table 8. Group contribution coefficients (kJ/mole) for calculation of the activity coefficient in water Groups Environmental Descriptor X Y Z YY RG FU AR BR2 BR3 BIP −CH3 0.958 0.711 1.04 ------−CH2 0.687/-0.018* 0.334 0.19 0.491 0.520 ------−CH -0.100 -0.342 -- 0.000 0.254 0.513 0.312 ------−C -0.662 -0.890 -- -- -0.291 0 0.112 0.290 0.488 0.353 =CH2 0.627 ------=CH 0.284 0.290 -- -- 0.269 ------=C -0.044 -0.230 -- -- 0.087 ------≡CH 0 ------≡C 0 ------=C= 0 ------RING ------0 -- 0 ------

* (X−CH2)2

w γ Calc log 4

0 0 4 8 12 Exp logγw Figure 14. Calculated versus experimental activity coefficient in water (——): Line of identity; N=188

4.16 Solubility in Octanol (So)

Since octanol is commonly regarded as a surrogate for biological lipids, the octanol solubility of a solute can be regarded as its solubility in the lipid regions of organisms.

The molar solubility of a solute in octanol at 298K, So, is given by

log S = log FR − log γ o o (36)

where FR and γo represent the fugacity ratio and the activity coefficient in octanol

discussed in Sections 4.12 and 4.14 respectively.

Figure 15 shows the predicted octanol solubilities for 25 hydrocarbons in this study

that have experimental So data. Equation 37 provides a good estimation of the octanol solubility with an AAE of 0.29 and R2 of 0.95.

0 o S Calc log -2

-4 -4 -2 0 2 Exp log So Figure 15. Calculated versus experimental octanol solubility (——): Line of identity; N=24

4.17 Solubility in Water (Sw)

The solubility of a solute in water at 298K is dependent upon its pure component properties and aqueous affinity. The former is related to the aqueous activity coefficient of the solute and the latter is related to its state of matter. The aqueous solubility of a solute is described by

log S w = log FR − logγ w (37)

where FR and γw represent the fugacity ratio and the activity coefficient in water discussed in Section 4.12 and 4.15 respectively.

Figure 16 shows that the predicted logarithmic aqueous solubilities are in good agreement with the experimental values through the line of identity. The AAE is 0.31 and the R2 is 0.94. Clearly, equation 38 gives a relatively accurate estimation of aqueous solubilities of the compounds studied.

-4 w S EXP log -8

-12 -12 -8 -4 0 Exp log Sw Figure 16. Calculated versus experimental aqueous solubility (——): Line of identity; N=192

4.18 Air-Octanol Partition Coefficient (Kao)

The air-octanol partition coefficient, Kao, is defined as the ratio of the concentration of the solute in the vapor phase, Cvap, to its concentration in octanol, Co,

log K ao = log Cvap − log Co (38)

Since vapor concentration (in mol/L) is related to vapor pressure (in atm) by

C = VP (39) vap R T the air-octanol partition coefficient becomes

log K = log VP − log S (40) ao ( RT ) o

At 298K this becomes

log Kao = logVP − log So −1.39 (41)

As seen in Figure 17, the calculated air-octanol partition coefficients are in good

agreement with the experimental values through the line of identity. The AAE is 0.49 and the R2 of the prediction is 0.95.

-4 ao

-8 Calc log K

-12

-16 -16 -12 -8 -4 0 Exp log Kao Figure 17. Calculated versus experimental Air-Octanol Partition Coefficient (——): Line of identity; N=122

4.19 Air-Water Partition Coefficient (Kaw)

Similarly, the Air-Water Partition Coefficient at 298K, Kaw, is described by

log Kaw = logVP − log Sw −1.39 (42)

K 0 Calc log -4

-8 -8 -4 0 4 Exp log Kaw Figure 18. Calculated versus experimental Air-Water Partition Coefficient (——): Line of identity; N=122

By using Equation 43, the air-water partition coefficients of the compounds studied are well predicted with an AAE of 0.36 and R2 of 0.94.

4.20 Octanol-Water Partition Coefficient (Kow)

The Octanol-water partition coefficient at 298K, Kow, can be described as the ratio of

the concentration of the solute in octanol, Co, and in water, Cw, respectively.

Co Kow = (43) Cw

This can be expressed in terms of activity coefficients, i.e.,

log K ow = log γ w − log γ o (44)

The predicted octanol-water partition coefficient values can be seen from Figure 19 to

2 be in good agreement with the experimental values. The R for logKow prediction is 0.94 and AAE is 0.30.

8 ow K

EXP log 4

0 0 4 8 12 Exp log Kow Figure 19. Calculated versus experimental Octanol-Water Partition Coefficient (——): Line of identity; N=170

5. SUMMARY

The UPPER scheme utilizes four sets of group contribution values to calculate the heat of boiling, the total heat of melting, molar volume and the aqueous activity coefficient. UPPER also uses four mutually orthogonal geometric parameters (symmetry, flexibility and aromatic and aliphatic eccentricity) to calculate the entropic properties. It is these geometric parameters that enable UPPER to accurately estimate transition entropies and therefore transition temperatures.

The key equations used to calculate all of the 20 properties considered are given in

Table 9. Each equation contains only the above additive-constitutive and geometric parameters and parameters that are determined by equations that precede it in the table or that lie above it in the UPPER scheme of Figure 1. Therefore all of the properties are calculated from the four sets of additive constitutive properties and the four entropy determining parameters.

The results, which are summarized in Table 10, show the number of compounds considered, the range of the data, and the average absolute error for each property. The seven asterisked properties listed in Table 10 were calculated form regression generated parameters. The remaining 13 properties are predicted strictly from the equations listed above without any training set. It is clear that the predictions are in good agreement with the measured values.

Table 9: Summary of UPPER relationships for physicochemical property calculation Eq # Symbol Equation

9 ∆Sb = 83.78 + 1.29 logσ + 0.6 φ + 5.76 logεar + 1.21 logεal

10 ∆Cpb = − 51.7 +14.23 logσ − 5.0 φ − 8.29 logε ar − 9.58 logε al

14 ∆Sm = 43.54 − 8.95 log σ + 8.02 φ + 9.16 log ε ar + 9.43 log ε al

15 ∆Cpm = 0 ∆ 17 Hb = ∑ nibi ∆ 20 Hm = ∑ nimi ∆Hb 21 Tb = ∆S b ∆H m 22 Tm = ∆S m

23 ∆Hsub = ∆H b + ∆H m + ∆Cpb (Tb − 298)

24 V = ∑ nivi ∆E 25 δ = v V ∆S (T −T ) ∆Cp (T −T ) 2.303 ∆Cp  T  26 log GLFR = b b − b b + b log b  2.303RT 2.303RT R  T  ∆S (T − T ) ∆Cp (T − T ) 2.303 ∆Cp  T  27 log CLFR = − m m + m m − m log m  2.303RT 2.303RT R  T  29 log VP = logCGFR = log LGFR + logCLFR 2 2 Vu (δoct − δu ) φoct 34 log γo = γ = oct 2.3RT γ 35 log w = ∑ niqi

36 log So = log FR − log γ o

37 log Sw = log FR − log γ w

41 log Kao = logVP −1.39 − log So

42 log Kaw = logVP −1.39 − log S w

44 log Kow = log γ w − log γ o

Table 10: Summary of UPPER calculation results

PhyChem Number of R Range of data Average Units Property compounds Square low high abs. error ∆Sb∗ 470 0.68 80.47 95.79 1.14 J/K mole ∆Cpb∗ 182 0.83 -138.71 -23.38 5.46 J/K mole ∆Sm∗ 352 0.98 21.10 506.85 7.06 J/K mole ∆Cpm Set equal to 0, not measured experimentally J/K mole ∆Ηb∗ 470 0.99 18.42 74.26 0.61 kJ/mole ∆Ηm∗ 352 0.99 2.86 185.00 1.80 kJ/mole Tb 537 0.99 225.00 809.00 7.26 K Tm 561 0.90 85.50 637.20 23.47 K ∆Ηsub 66 0.96 18.30 170.40 6.23 kJ/mole V* 312 1.00 78.28 336.50 1.27 cm3/mole δ 163 0.96 13.68 20.27 0.21 (J/cm3)1/2 FR Calculated, not measured experimentally unitless logVP 335 0.99 -11.16 1.84 0.16 log (atm) logγο Calculated, not measured experimentally log(mole/L) logγω∗ 188 0.93 1.04 9.45 0.26 log(mole/L) logSo 24 0.95 -3.00 0.75 0.29 log(mole/L) logSw 190 0.92 -9.45 -1.04 0.33 log(mole/L) logKao 122 0.95 -11.78 -0.21 0.49 unitless logKaw 122 0.94 -5.24 2.58 0.36 unitless logKow 170 0.94 0.94 9.36 0.30 unitless

6. CONCLUSION

In this study, a simple and widely applicable model, UPPER, for estimating physicochemical properties by integrating both group-contribution and molecular geometry with sound thermodynamic relationships is developed. The proposed model provides a simple and accurate prediction of the properties studied as evidenced by Table

10. UPPER can lead to the efficient design and synthesis of organic compounds having optimal physicochemical properties in science and industry.

7. APPENDIX A – SUPPLEMENTARY DATA

SI Table 1. Experimental and calculated values of heat of boiling, entropy of boing and boiling point

Compound ΔHb(kJ/mole) ΔSb(J/K mole) Tb(K) Exp Calc Exp Calc Exp Calc Propadiene 20.60 21.44 86.33 85.46 238.60 250.88 Propyne 22.25 22.61 88.99 85.50 250.00 264.47 Propylene 18.42 20.87 81.87 83.78 225.00 249.15 Cyclopropane 20.06 21.01 83.51 85.36 240.20 246.07 Propane 19.04 21.82 82.46 84.17 230.90 259.29 2-Methylpropane 21.30 23.66 81.47 84.40 261.44 280.39 n-Butane 22.44 24.31 82.35 84.38 272.50 288.05 1,3-Butadiene 22.47 23.58 83.62 84.17 268.70 280.18 1-Butyne 24.52 24.97 87.20 83.78 281.20 298.07 1,2-Butadiene 24.40 24.46 85.92 83.78 284.00 292.00 2-Butyne 26.90 26.94 89.70 85.46 299.90 315.29 2-Methylpropene 22.21 23.33 83.48 84.17 266.10 277.14 1-Butene 22.07 23.29 82.69 84.08 266.90 277.02 trans-2-Butene 23.02 23.90 84.01 84.17 274.00 283.93 cis-2-Butene 23.34 23.90 84.26 84.17 277.00 283.93 Cyclobutane 24.19 23.93 84.70 85.67 285.60 279.33 1,3-Cyclopentadiene 25.76 27.72 82.04 85.01 314.00 326.03 3-Methyl-1-butene 24.10 24.81 82.22 83.78 293.10 296.07 1-Pentene 25.20 25.82 81.82 84.68 308.00 304.94 2-Methyl-1-butene 25.50 25.74 83.80 84.08 304.30 306.18 trans-2-Pentene 26.25 26.32 84.88 84.38 309.30 311.87 cis-2-Pentene 26.54 26.32 85.80 84.38 309.30 311.87 2-Methyl-2-butene 26.31 26.35 84.41 83.78 311.70 314.51 1,1-Dimethylcyclopropane 24.56 24.18 83.64 84.75 293.60 285.34 Cyclopentane 27.30 26.86 84.70 85.92 322.30 312.60 2,2-Dimethylpropane 22.75 24.94 80.50 85.46 282.60 291.83 2-Methylbutane 24.69 26.19 82.03 84.08 301.00 311.54 n-Pentane 25.79 26.74 83.41 84.98 309.20 314.66 1,4-Pentadiene 24.49 25.97 81.91 84.38 299.00 307.73 2-Methyl-1,3-butadiene 25.80 26.16 83.98 83.78 307.20 312.21 1-Pentyne 27.32 27.50 87.24 84.38 313.10 325.93 3-Methyl-1,2-butadiene 27.24 26.92 86.80 83.78 313.83 321.27

1,trans-3-Pentadiene 26.57 26.61 84.35 84.08 315.00 316.44 cis-1,3-Pentadiene 26.70 26.61 84.75 84.08 315.00 316.44 1,2-Pentadiene 27.57 26.88 86.73 84.08 317.90 319.72 2,3-Pentadiene 27.76 27.49 86.43 84.17 321.20 326.58 2-Pentyne 29.25 29.30 88.87 83.78 329.10 349.77 Methylenecyclobutane 26.47 26.72 83.98 84.90 315.20 314.75 Cyclopentene 27.60 27.29 87.01 85.01 317.20 320.97 Spiropentane 26.76 26.00 85.77 85.40 312.00 304.43 1-hexen-5-yne 29.04 28.97 84.64 84.68 343.15 342.11 1,5-Hexadiene 27.54 27.29 82.85 84.98 332.40 321.13 2,3-Dimethyl-1,3-butadiene 28.91 28.73 84.58 84.17 341.80 341.36 trans-1,3-Hexadiene 29.44 29.02 85.03 84.68 346.20 342.75 trans-2,4-Hexadiene 30.68 29.63 86.37 84.77 355.20 349.54 1-Hexyne 30.45 29.98 88.43 84.98 344.30 352.84 3-Methylcyclopentene 28.87 29.03 85.45 84.63 337.90 342.99 1-Methylcyclopentene 29.05 29.19 83.37 84.63 348.50 344.95 Cyclohexene 30.46 30.21 85.56 84.72 356.00 356.62 3,3-Dimethyl-1-butene 25.93 26.62 82.51 83.78 314.20 317.75 3-Methyl-1-pentene 26.90 27.34 82.21 84.38 327.20 323.95 4-Methyl-1-pentene 27.10 27.66 82.90 84.38 326.90 327.83 2,3-Dimethyl-1-butene -- 27.26 -- 83.78 328.60 325.34 cis-4-Methyl-2-pentene 27.50 27.83 82.83 84.08 332.00 330.98 trans-4-methyl-2-pentene 27.60 27.83 83.13 84.08 332.00 330.98 2-Methyl-1-pentene 28.10 28.27 83.86 84.68 335.10 333.89 1-Hexene 28.30 28.30 84.13 85.28 336.40 331.89 2-Ethyl-1-butene 28.35 28.16 83.94 84.68 337.70 332.57 cis-3-Methyl-2-pentene 28.92 28.77 84.88 84.38 340.70 340.93 2-Methyl-2-pentene 28.90 28.77 84.93 84.38 340.30 340.93 cis-3-Hexene 28.70 28.73 84.39 84.98 340.10 338.13 trans-3-Hexene 28.90 28.73 84.98 84.98 340.10 338.13 trans-2-Hexene 28.90 28.85 85.50 84.98 338.00 339.44 cis-2-Hexene 29.10 28.85 86.09 84.98 338.00 339.44 trans-3-Methyl-2-pentene 28.80 28.77 84.53 84.38 340.70 340.93 2,3-Dimethyl-2-butene 29.64 28.80 85.59 84.17 346.30 342.20 Ethylcyclobutane 28.67 28.20 83.37 84.81 343.90 332.51 Methylcyclopentane 29.08 28.60 84.29 84.63 345.00 337.91 Cyclohexane 29.97 29.78 84.68 85.73 353.90 347.42 2,2-Dimethylbutane 26.31 27.47 81.53 84.08 322.70 326.70 2,3-Dimethylbutane 27.38 28.03 82.74 83.78 330.90 334.61 2-Methylpentane 27.79 28.68 83.35 84.68 333.40 338.64

3-Methylpentane 28.06 28.68 83.41 84.68 336.40 338.64 n-Hexane 28.85 29.13 84.43 85.58 341.70 340.34 Benzene 30.72 29.50 86.95 89.65 353.30 329.04 1,3,5-Hexatriene 29.92 32.63 84.76 84.38 353.00 386.66 1,4-Cyclohexadiene 32.26 30.64 89.99 86.11 358.50 355.84 1,3-Cyclohexadiene -- 30.64 -- 86.11 353.50 355.84 1,6Heptadiene -- 29.82 -- 85.58 363.00 348.45 1-Heptyne 31.88 32.42 85.53 85.58 372.70 378.80 4-Methylcyclohex-1-ene 31.80 31.95 84.56 84.72 376.00 377.14 3-Ethylcyclopentene 31.58 31.56 85.16 84.93 370.80 371.57 (dl)-1,5-Dimethylcyclopentene 31.60 30.93 84.93 84.63 372.00 365.50 1,2-Dimethylcyclopentene 31.93 31.10 84.29 85.01 378.80 365.79 1-Ethylcyclopentene -- 31.61 -- 84.93 379.30 372.21 1-Methylcyclohexene 32.47 32.12 84.99 84.72 382.00 379.10 Cycloheptene 33.25 33.14 85.70 85.19 388.00 389.00 Methylenecyclohexane 32.01 32.57 85.24 84.72 375.50 384.47 trans-2-Heptene 31.73 31.33 85.51 85.58 371.00 366.07 cis-3-Methyl-3-hexene 31.28 31.19 81.14 84.98 385.50 366.98 4,4-Dimethylpent-1-ene -- 28.94 -- 84.38 345.50 342.94 3,3-Dimethylpent-1-ene 29.17 29.15 83.23 84.38 350.50 345.47 trans-4,4-Dimethylpent-2-ene -- 29.65 -- 84.08 353.40 352.58 2,3,3-Trimethyl-1-butene 29.29 29.07 83.47 83.78 350.90 347.02 cis-4,4-Dimethylpent-2-ene 29.42 29.65 83.26 84.08 353.40 352.58 (dl)3,4-Dimethylpent-1-ene 29.75 29.18 84.09 84.08 353.80 346.99 2,4-Dimethylpent-1-ene 29.86 30.11 84.21 84.38 354.60 356.89 2,4-Dimethylpent-2-ene -- 30.28 -- 84.08 356.40 360.15 2,3-Dimethyl-1-pentene 30.10 29.79 84.23 84.38 357.30 353.01 (dl)3-Methyl-1-hexene 30.73 29.82 86.11 84.98 356.90 350.87 3-Ethyl-1-pentene 30.68 29.82 85.90 84.98 357.10 350.87 5-Methyl-1-hexene 30.42 30.19 84.87 84.98 358.40 355.28 trans-2-Methyl-3-hexene -- 30.25 -- 84.68 358.90 357.19 2-Methyl-cis-3-hexene 30.41 30.25 84.70 84.68 359.00 357.19 (dl)4-Methyl-1-hexene 30.62 30.19 85.13 84.98 359.70 355.28 4-Methyl-trans-2-hexene 30.55 30.36 84.71 84.68 360.60 358.51 2-Ethyl-3-methyl-1-butene -- 29.68 -- 84.38 362.00 351.68 trans-5-Methyl-2-hexene 30.59 30.69 84.72 84.68 361.10 362.38 cis-3,4-Dimethylpent-2-ene 30.46 30.28 84.15 84.08 362.00 360.15 5-Methyl-cis-2-hexene -- 30.69 -- 84.68 363.00 362.38 trans-3,4-Dimethylpent-2-ene 30.66 30.28 84.70 84.08 362.00 360.15 2-Methyl-1-hexene 31.06 30.76 85.10 85.28 365.00 360.65

1-Heptene 31.10 30.74 84.90 85.88 366.30 357.92 3-Methyl-trans-3-hexene 31.12 31.19 80.71 84.98 385.50 366.98 2-Ethyl-1-pentene -- 30.69 -- 85.28 367.00 359.90 2-Methyl-2-hexene 31.28 31.30 84.91 84.98 368.40 368.30 3-Methyl-trans-2-hexene 31.26 31.30 84.83 84.98 368.50 368.30 3-Ethyl-2-pentene -- 31.19 -- 84.98 369.00 366.98 trans-3-Heptene -- 31.26 -- 85.58 368.70 365.32 cis-3-Heptene 31.58 31.26 85.66 85.58 368.70 365.32 2,3-dimethylpent-2-ene 31.22 31.22 84.26 84.38 370.50 369.99 cis-3-methyl-2-hexene 31.45 32.69 85.31 84.98 368.60 384.68 cis-2-Heptene 31.16 31.33 83.99 85.58 371.00 366.07 1,1-Dimethylcyclopentane -- 30.03 -- 85.01 360.90 353.27 cis-1,3-Dimethylcyclopentane 30.40 30.34 83.56 84.63 363.80 358.46 (dl)-trans-1,3-Dimethylcyclopentane 31.37 30.34 86.23 85.01 363.80 356.82 (dl)-trans-1,2-Dimethylcyclopentane 30.86 30.34 84.55 85.01 365.00 356.82 cis-1,2-Dimethylcyclopentane 31.70 30.34 85.10 84.63 372.50 358.46 Ethylcyclopentane 31.96 31.13 84.89 84.93 376.50 366.51 Methylcyclohexane 31.27 31.52 83.59 84.72 374.10 372.07 Cycloheptane 33.55 32.71 85.71 84.80 391.40 385.71 2,2-Dimethylpentane 29.23 29.95 82.95 84.68 352.40 353.70 2,2,3-Trimethylbutane 28.90 29.31 81.68 84.17 353.80 348.22 2,4-Dimethylpentane 29.55 30.56 83.55 84.38 353.70 362.22 3,3-Dimethylpentane 29.62 29.95 82.51 84.68 359.00 353.70 (dl)2,3-Dimethylpentane 30.46 30.56 83.98 84.38 362.70 362.22 2-Methylhexane 30.62 31.11 84.35 85.28 363.00 364.80 (dl)3-Methylhexane 30.89 31.11 84.86 85.28 364.00 364.80 3-Ethylpentane 31.12 31.11 84.89 85.28 366.60 364.80 n-Heptane 31.77 31.46 85.50 86.18 371.60 365.10 Toluene 33.18 32.74 86.45 88.65 383.80 369.28 Cycloheptatriene 35.32 34.00 90.56 85.19 390.00 399.09 Ethylbenzene 35.57 35.16 86.95 88.56 409.10 396.95 1,4-Dimethylbenzene 35.67 35.97 86.68 89.04 411.50 404.03 1,3-Dimethylbenzene 35.66 35.97 86.49 88.65 412.30 405.80 1,2-Dimethylbenzene 36.24 35.97 86.78 88.65 417.60 405.80 (dl)-trans1,2-Divinylcyclobutane 33.02 33.35 85.64 84.81 385.50 393.27 (dl)-4-Vinyl-1-cyclohexene 33.50 34.92 83.29 84.72 402.20 412.22 cis-1,5-Cyclooctadiene 37.50 36.50 88.45 85.26 424.00 428.04 1-Octyne 35.83 34.80 89.73 86.18 399.30 403.85 4-Octyne 36.00 36.68 88.95 85.58 404.70 428.56 3-Octyne 36.94 36.68 90.92 85.58 406.30 428.56

2-Octyne 37.26 36.75 90.72 85.58 410.70 429.42 Allylcyclopentane 34.19 32.59 85.90 85.23 398.00 382.44 Vinylcyclohexane 34.47 34.49 85.97 84.72 401.00 407.15 Ethylidenecyclohexane -- 35.60 -- 84.72 409.00 420.16 Cyclooctene 36.13 36.07 87.90 84.87 411.00 424.93 cis-Bicyclo[3.3.0]octane 35.51 34.02 86.83 85.26 409.00 398.95 3,3-Dimethyl-1-hexene 31.68 31.63 84.03 84.98 377.00 372.24 3-Methyl-1-heptene 32.91 32.25 85.70 85.58 384.00 376.85 2,4,4-Trimethyl-1-pentene 30.99 31.39 82.85 84.38 374.00 372.00 trans-2,2-Dimethyl-3-hexene 31.33 32.06 83.80 84.68 373.80 378.64 trans-2,5-Dimethyl-3-hexene 31.74 31.76 84.58 84.77 375.20 374.67 5,5-Dimethyl-1-hexene 31.55 31.47 83.68 84.98 377.00 370.29 3,4,4-Trimethyl-1-pentene 31.40 30.45 83.29 84.08 377.00 362.16 3-Methyl-2-isopropyl-1-butene 31.75 31.19 84.21 84.08 377.00 370.93 5,5-Dimethyl-trans-2-hexene 31.61 31.96 83.78 84.68 377.30 377.43 3,5-Dimethyl-1-hexene 31.99 31.71 84.86 84.68 377.00 374.41 2,4,4-Trimethyl-2-pentene 31.90 32.10 84.41 84.08 377.90 381.74 3,3,4-Trimethyl-1-pentene 31.49 30.99 83.30 84.08 378.00 368.59 cis-2,2-Dimethyl-3-hexene 31.73 32.06 84.88 84.68 373.80 378.64 5,5-Dimethyl-cis-2-hexene -- 31.96 -- 84.68 379.90 377.43 4,4-Dimethyl-1-hexene 31.96 31.47 84.03 84.98 380.35 370.29 2,3,3-Trimethyl-1-pentene 31.82 31.60 83.44 84.38 381.30 374.53 2,3,4-Trimethyl-1-pentene 32.05 31.63 84.11 84.08 381.00 376.15 2,4-Dimethyl-trans-3-hexene 32.27 32.70 84.71 84.68 381.00 386.15 4-Methyl-3-ethyl-1-pentene -- 31.71 -- 84.68 380.70 374.41 2,4-Dimethyl-cis-3-hexene 32.40 32.70 84.81 84.68 382.00 386.15 4,5-Dimethyl-1-hexene 32.44 32.03 84.91 84.68 382.00 378.27 3-Ethyl-2-methyl-1-pentene 32.57 32.27 85.14 84.98 382.50 379.72 3,3-Dimethyl-2-ethyl-1-butene 31.96 31.49 83.46 84.38 383.00 373.20 3-Ethyl-1-hexene 32.85 32.25 85.69 85.58 383.30 376.85 2,4-Dimethyl-2-hexene 32.54 32.81 84.74 84.68 384.00 387.47 2,4-Dimethyl-1-hexene 32.67 32.64 85.01 84.98 384.35 384.14 2,3-Dimethyl-1-hexene 32.61 32.27 85.03 84.98 383.50 379.72 2,5-Dimethyl-2-hexene 32.68 33.14 84.84 84.68 385.20 391.33 3,4-Dimethyl-1-hexene 32.70 31.71 84.95 84.68 385.00 374.41 3-Methyl-3-ethyl-1-pentene 32.38 31.63 84.40 84.98 383.70 372.24 2,5-Dimethyl-1-hexene 32.71 32.64 85.04 84.98 384.60 384.14 2-Isopropyl-1-pentene 32.83 32.21 85.06 84.98 386.00 378.97 2-Ethyl-3-methyl-1-pentene 32.70 32.21 84.82 84.98 385.50 378.97 4-Ethyl-1-hexene 32.61 32.67 84.99 85.58 383.69 381.79

4-Methyl-1-heptene 33.07 32.67 85.72 85.58 385.80 381.79 5-Methyl-1-heptene 33.12 32.67 85.72 85.58 386.30 381.79 6-Methyl-1-heptene 33.11 32.67 85.72 85.58 386.20 381.79 4-Methyl-3-ethyl-trans-2-pentene 32.87 32.70 84.93 84.68 387.00 386.15 2-Methyl-trans-3-heptene 32.92 32.78 85.50 85.28 385.00 384.35 trans-3,4-Dimethyl-3-hexene 33.60 33.64 86.60 84.98 387.95 395.83 2,3,4-Trimethyl-2-pentene 32.79 32.73 84.19 84.08 389.50 389.31 4-Methyl-3-ethyl-cis-2-pentene 33.02 32.70 84.88 84.68 389.00 386.15 2-Methyl-1-heptene 33.70 33.19 85.89 85.88 392.30 386.47 2-Ethyl-1-hexene 34.11 33.17 86.80 85.88 393.00 386.28 1-Octene 34.07 33.12 86.38 86.48 394.40 383.02 2,3-Dimethyl-2-hexene 33.58 33.75 85.04 84.98 394.80 397.15 trans-4-Octene 33.72 33.75 85.29 86.18 395.30 391.58 2-Methyl-2-heptene 33.91 33.78 85.72 85.58 395.60 394.72 cis-3-Octene 34.20 33.75 86.30 86.18 396.30 391.58 cis-4-Octene 34.17 33.75 86.44 86.18 395.30 391.58 trans-2-Octene 33.67 33.76 84.59 86.18 398.00 391.76 tran-3-Octene -- 33.75 -- 86.18 396.30 391.58 cis-2-Octene 34.45 33.76 86.56 86.18 398.00 391.76 cis-1,3-Dimethylcyclohexane 32.91 33.26 83.74 84.72 393.00 392.59 trans-1,3-Dimethylcyclohexane 33.39 33.26 83.98 84.72 397.60 392.59 cis-1,4-Dimethylcyclohexane 33.28 33.26 83.83 84.72 397.00 392.59 trans-1,4-Dimethylcyclohexane 32.56 33.26 82.93 85.11 392.60 390.80 1,1,3-Trimethylcyclopentane 31.67 31.77 83.79 84.63 377.90 375.44 1,2(cis),3(trans)-trimethylcyclopentane 32.68 32.07 83.59 84.63 391.00 379.01 1,1,2-Trimethylcyclopentane 32.44 31.77 83.83 84.63 387.00 375.44 1,cis-2,cis-4-Trimethylcyclopentane -- 32.07 -- 84.63 390.00 379.01 1,cis-2,trans-4-Trimethylcyclopentane 32.62 32.07 83.63 84.63 390.00 379.01 1-Ethyl-1-methylcyclopentane 33.20 32.56 84.11 84.93 394.70 383.43 1,cis-2,cis-3-Trimethylcyclopentane 33.17 32.07 83.84 84.63 395.60 379.01 Isopropylcyclopentane 33.56 32.97 83.98 84.63 399.60 389.55 (dl)-cis-1-Ethyl-2-methylcyclopentane 33.99 32.87 84.76 84.93 401.00 386.99 Propylcyclopentane 34.70 33.61 85.89 85.53 404.00 392.96 1,trans-2-Dimethylcyclohexane 32.96 33.26 83.09 84.72 396.70 392.59 1,1-Dimethylcyclohexane 32.51 32.96 82.81 84.72 392.60 389.03 cis-1,2-Dimethylcyclohexane 33.47 33.26 83.07 84.72 402.90 392.59 Ethylcyclohexane 34.04 34.05 84.07 85.02 404.90 400.51 Cyclooctane 35.92 35.64 85.12 85.65 422.00 416.06 3-Ethyl-2-methylpentane 32.93 33.05 84.70 84.98 388.80 388.87 2,3-Dimethylhexane 33.17 33.05 85.36 84.98 388.60 388.87

2,2,4-Trimethylpentane 30.79 31.84 82.68 84.38 372.40 377.33 2,2,3,3-Tetramethylbutane 31.42 30.58 82.78 85.17 379.60 359.08 2,2-Dimethylhexane 32.07 32.39 83.95 85.28 382.00 379.75 2,4-Dimethylhexane 32.51 33.05 84.97 84.98 382.60 388.87 2,5-Dimethylhexane 32.54 33.05 85.16 84.98 382.10 388.87 2,2,3-Trimethylpentane 31.94 31.84 83.39 84.38 383.00 377.33 3,3-Dimethylhexane 32.31 32.39 83.90 85.28 385.10 379.75 2,3,4-Trimethylpentane 32.36 32.40 83.73 84.08 386.50 385.39 2,3,3-Trimethylpentane 32.12 31.84 82.80 84.38 387.90 377.33 3,4-Dimethylhexane 33.24 33.05 85.08 84.98 390.70 388.87 2-Methylheptane 33.26 33.50 85.11 85.88 390.80 390.03 4-Methylheptane 33.35 33.50 85.36 85.88 390.70 390.03 3-Ethyl-3-methylpentane 32.78 32.39 83.75 85.28 391.40 379.75 3-Methylheptane 33.66 33.50 86.09 85.88 391.00 390.03 3-Ethylhexane 33.59 33.50 85.75 85.88 391.70 390.03 n-Octane 34.41 33.75 86.31 86.78 398.70 388.96 Styrene 36.38 36.27 87.04 88.26 418.00 410.97 Cyclooctatetraene 36.40 37.36 88.03 86.04 413.50 434.17 a-Methylstyrene 38.54 39.55 87.92 88.26 438.40 448.13 trans-Methylstyrene 38.74 39.30 85.84 88.56 451.30 443.72 Indane 39.63 40.47 87.89 88.84 450.90 455.53 Isopropylbenzene 37.53 36.67 88.31 88.26 425.00 415.44 Propylbenzene 38.24 37.69 88.48 89.16 432.20 422.66 3-Ethyltoluene 39.25 38.39 90.38 88.56 434.30 433.50 4-Ethyltoluene 38.41 38.39 88.30 88.56 435.00 433.50 2-Ethyltoluene 38.87 38.39 88.68 88.56 438.30 433.50 1,3,5-Trimethylbenzene 39.04 39.21 89.19 89.27 437.70 439.26 1,2,3-Trimethylbenzene 40.04 39.21 89.14 88.65 449.20 442.31 1,2,4-Trimethylbenzene 39.09 39.21 88.38 88.26 442.30 444.26 1-Nonyne 37.12 37.14 87.59 86.78 423.80 428.00 Allylcyclohexane -- 35.52 -- 85.32 430.50 416.31 trans-Hexahydroindan 37.60 36.94 86.60 84.93 434.20 434.93 cis-Hexahydroindan -- 36.94 -- 84.93 441.00 434.93 2,6-Dimethyl-1-heptene -- 35.13 -- 85.58 415.00 410.45 1-Nonene 36.32 35.46 86.50 87.08 419.90 407.23 1,1,3-Trimethylcyclohexane 34.41 34.70 84.01 84.72 409.60 409.55 Propylcyclohexane 36.07 36.53 83.94 85.62 429.70 426.69 Isopropylcyclohexane 36.67 35.89 85.71 84.72 427.80 423.65 Butylcyclopentane 36.16 36.04 84.13 86.13 429.80 418.48 3-Methyl-3-ethylhexane 35.73 34.77 86.39 85.88 413.60 404.88

2,2,4,4-Tetramethylpentane 32.51 33.11 82.30 84.38 395.00 392.44 2,2,5-Trimethylhexane 33.65 34.32 84.72 84.98 397.20 403.87 2,2,4-Trimethylhexane 34.02 34.32 85.14 84.98 399.60 403.87 2,3,5-Trimethylhexane 34.43 34.93 85.12 84.68 404.50 412.54 2,4,4-Trimethylhexane -- 34.32 -- 84.98 403.70 403.87 2,2-Dimethylheptane 34.60 34.77 85.28 85.88 405.70 404.88 2,2,3,4-Tetramethylpentane 33.70 33.68 83.00 84.08 406.00 400.56 2,4-Dimethylheptane 35.36 35.48 87.10 85.58 405.90 414.58 2,2-Dimethyl-3-ethylpentane 34.37 34.32 84.49 84.98 406.80 403.87 2,2,3-Trimethylhexane 34.77 34.32 85.51 84.98 406.60 403.87 2-Methyl-4-ethylhexane 35.65 35.48 87.63 85.58 406.80 414.58 4,4-Dimethylheptane 35.36 34.77 86.61 85.88 408.20 404.88 2,6-Dimethylheptane 35.38 35.48 86.68 85.58 408.20 414.58 3,5-Dimethylheptane 35.65 35.48 87.16 85.58 409.00 414.58 2,5-Dimethylheptane 35.61 35.48 87.06 85.58 409.00 414.58 2,4-Dimethyl-3-ethylpentane 34.73 34.93 84.78 84.68 409.70 412.54 3,3-Dimethylheptane 35.04 34.77 85.39 85.88 410.30 404.88 2,3,3-Trimethylhexane 34.98 34.32 85.17 84.98 410.70 403.87 2,3,4-Trimethylhexane 35.69 34.93 86.61 84.68 412.10 412.54 2,2,3,3-Tetramethylpentane 34.30 33.11 82.97 84.38 413.40 392.44 3-Methyl-4-ethylhexane 36.40 35.48 88.14 85.58 413.00 414.58 3,3,4-Trimethylhexane 35.15 34.32 85.00 84.98 413.50 403.87 2,3-Dimethylheptane 36.11 35.48 87.32 85.58 413.50 414.58 3,4-Dimethylheptane 36.36 35.48 87.91 85.58 413.60 414.58 4-Ethylheptane 36.65 35.83 88.49 86.48 414.20 414.36 2,3,3,4-Tetramethylpentane 34.50 33.68 83.23 84.08 414.50 400.56 4-Methyloctane 36.19 35.83 87.11 86.48 415.40 414.36 3-Ethylheptane -- 35.83 -- 86.48 416.00 414.36 2-Methyloctane 36.10 35.83 86.74 86.48 416.20 414.36 3-Methyloctane 36.40 35.83 87.25 86.48 417.20 414.36 2,3-Dimethyl-3-ethylpentane 35.31 34.32 84.54 84.98 417.70 403.87 3,3-Diethylpentane 34.61 34.77 82.54 85.88 419.30 404.88 n-Nonane 36.91 36.00 87.09 87.38 423.80 411.95 Indene 40.94 40.90 89.97 89.23 455.00 458.37 Benzene, 1-ethenyl-2-methyl- -- 39.51 -- 88.26 443.00 447.64 1,4-Dihydronaphthalene 42.41 43.83 87.54 89.38 484.50 490.33 1,2,3,4-Tetrahydronaphthalene 42.35 43.40 88.12 88.99 480.60 487.64 1,3-Dimethyl-4-ethylbenzene 40.95 41.63 88.76 88.56 461.40 470.05 1,2,3,5-Tetramethylbenzene 42.61 42.45 90.46 88.65 471.00 478.82 tert-Butylbenzene 38.44 38.48 86.95 88.26 442.10 436.02

Isobutylbenzene -- 39.53 -- 88.86 445.70 444.79 (dl)-sec-Butylbenzene 37.95 39.20 84.99 88.86 446.50 441.11 3-Isopropyltoluene 38.12 39.91 85.07 88.26 448.10 452.12 4-Isopropyltoluene 39.75 39.91 88.42 88.26 449.50 452.12 2-Isopropyltoluene 39.38 39.91 87.29 88.26 451.10 452.12 1,3-Diethylbenzene 40.33 40.81 88.82 89.16 454.10 457.71 3-Propyltoluene 40.25 40.92 88.46 89.16 455.00 458.96 4-Propyltoluene 39.71 40.92 87.00 89.16 456.40 458.96 1,2-Diethylbenzene 40.25 40.81 88.06 89.16 457.00 457.71 Butylbenzene 38.87 40.17 85.24 89.76 456.00 447.48 1,3-Dimethyl-5-ethylbenzene 40.73 41.63 89.20 88.56 456.60 470.05 1,4-Diethylbenzene 40.58 40.81 89.39 89.16 454.00 457.71 2-Propyltoluene 40.52 40.92 88.47 89.16 458.00 458.96 1,4-Dimethyl-2-ethylbenzene 40.80 41.63 88.71 88.56 459.90 470.05 1,2-Dimethyl-4-ethylbenzene 41.70 41.63 90.17 88.56 462.50 470.05 1,3-Dimethyl-2-ethylbenzene 41.80 41.63 90.27 88.56 463.00 470.05 1,2-Dimethyl-3-ethylbenzene 41.64 41.63 89.16 88.56 467.00 470.05 1,2,3,4-Tetramethylbenzene 45.02 42.45 94.18 88.65 478.00 478.82 1,2,4,5-Tetramethylbenzene 42.48 42.45 90.37 89.04 470.00 476.74 7-Methyl-3-methylene-1,6-octadiene(myrcene) -- 38.05 -- 85.58 440.00 444.60 (d)-Limonene 39.14 39.28 86.98 84.72 450.00 463.65 5-Isopropyl-2-methyl-1,3-cyclohexadiene 39.91 38.66 89.68 84.72 445.00 456.28 (dl)-Limonene 38.28 39.28 84.88 84.72 451.00 463.65 (l)-Limonene 38.28 39.28 84.88 84.72 451.00 463.65 a-Pinene 35.74 36.60 83.42 84.80 428.50 431.59 Decalin -- 39.87 -- 85.77 460.30 464.83 Spiro[4.5]decane 39.86 40.63 87.04 84.99 458.00 478.04 trans-Bicyclo[4.4.0]decane 38.62 39.87 83.90 85.38 460.30 466.95 cis-Bicyclo[4.4.0]decane 39.80 39.87 85.41 85.38 466.00 466.95 1-Decene 38.66 37.75 87.27 87.68 443.00 430.57 n-Pentylcyclopentane 38.95 38.43 85.99 86.73 453.00 443.10 tert-Butylcyclohexane 37.01 37.17 83.22 84.72 444.70 438.70 1-Isopropyl-4-methylcyclohexane -- 37.63 -- 84.72 443.00 444.17 Isobutylcyclohexane -- 38.42 -- 85.32 444.30 450.32 Butylcyclohexane 38.49 38.97 84.80 86.22 453.90 451.95 2,2,5,5-Tetramethylhexane 35.27 35.60 85.94 85.37 410.40 416.97 2,2-Dimethyl-4-ethylhexane -- 36.76 -- 85.58 420.00 429.48 2,2,4,5-Tetramethylhexane 35.82 36.21 85.09 84.68 420.90 427.60 2,2,3,5-Tetramethylhexane 36.23 36.21 85.98 84.68 421.40 427.60 2,2,4-Trimethylheptane 36.40 36.76 86.40 85.58 421.30 429.48

2,4,6-Trimethylheptane 36.90 37.42 87.74 85.28 420.60 438.74 2,2,6-Trimethylheptane 36.74 36.76 87.07 85.58 421.90 429.48 2,4,4-Trimethylheptane 36.36 36.76 85.75 85.58 424.00 429.48 2,2,5-Trimethylheptane 36.65 36.76 86.48 85.58 423.80 429.48 2,3,3,5-Tetramethylhexane 36.28 36.21 85.13 84.68 426.10 427.60 2,5,5-Trimethylheptane 36.78 36.76 86.37 85.58 425.80 429.48 2,2,4,4-Tetramethylhexane 35.06 35.60 82.15 84.98 426.80 418.88 2,5-Dimethyl-3-ethylhexane -- 37.42 -- 85.28 427.10 438.74 2,2,4-Trimethyl-3-ethylpentane 36.15 36.21 84.37 84.68 428.45 427.60 2,3,4,5-Tetramethylhexane 36.86 36.77 85.88 84.38 429.20 435.81 2,2-Dimethyl-3-ethylhexane 36.69 36.76 85.51 85.58 429.10 429.48 3,3,5-Trimethylheptane 36.40 36.76 84.91 85.58 428.70 429.48 2,3,6-Trimethylheptane 37.32 37.42 87.00 85.28 429.00 438.74 2-Methyl-4-ethylheptane 37.36 37.87 86.69 86.18 431.00 439.38 2,4-Dimethyloctane 36.47 37.87 85.01 86.18 429.00 439.38 2,4-Dimethyl-3-isopropylpentane 36.36 36.77 84.54 84.38 430.10 435.81 2,4,5-Timethylheptane 37.11 37.42 86.41 85.28 429.50 438.74 2,2-Dimethyloctane 37.15 37.11 86.80 86.48 428.00 429.10 2,2,3-Trimethylheptane -- 36.76 -- 85.58 430.80 429.48 3-Methyl-5-ethylheptane 37.70 37.87 87.43 86.18 431.20 439.38 4,4-Dimethyloctane 37.24 37.11 86.50 86.48 430.50 429.10 4-Propylheptane 38.12 38.12 88.54 87.08 430.50 437.80 2,2,3,4,4-Pentamethylpentane 35.31 34.95 81.69 84.08 432.30 415.72 2,2,3,4-Tetramethylhexane 36.40 36.21 84.65 84.68 430.00 427.60 4-Isopropylheptane 37.45 37.87 86.70 86.18 431.90 439.38 3,5-Dimethyloctane 37.74 37.87 87.28 86.18 432.40 439.38 2,5-Dimethyloctane 37.82 37.87 87.65 86.18 431.50 439.38 2,6-Dimethyloctane 38.20 37.87 88.14 86.18 433.40 439.38 2,2,3,3-Tetramethylhexane 36.20 35.60 83.54 84.98 433.30 418.88 2,3,3-Trimethylheptane 37.20 36.76 85.86 85.58 433.20 429.48 2,4-Dimethyl-3-ethylhexane 37.15 37.42 85.41 85.28 435.00 438.74 2,3,4-Trimethylheptane 37.32 37.42 85.99 85.28 434.00 438.74 2,7-Dimethyloctane 38.24 37.87 88.34 86.18 432.90 439.38 2-Methyl-5-ethylheptane 37.74 37.87 87.22 86.18 432.70 439.38 2,4-Dimethyl-4-ethylhexane 37.07 36.76 85.40 85.58 434.10 429.48 3,4,4-Trimethylheptane 37.07 36.76 85.40 85.58 434.10 429.48 2,3-Dimethyl-4-ethylhexane -- 37.42 -- 85.28 435.00 438.74 2,3,5-Trimethylheptane 37.15 37.42 85.67 85.28 433.70 438.74 3,6-Dimethyloctane 38.07 37.87 87.77 86.18 433.80 439.38 4-Methyl-4-ethylheptane 37.32 37.11 86.03 86.48 433.80 429.10

2-Methyl-3-ethylheptane 37.74 37.87 86.56 86.18 436.00 439.38 3,3-Dimethyloctane 37.61 37.11 86.63 86.48 434.20 429.10 2,3,4,4-Tetramethylhexane -- 36.21 -- 84.68 434.60 427.60 3,3-Dimethyl-4-ethylhexane 37.11 36.76 85.14 85.58 435.90 429.48 3,4-Dimethyl-3-ethylhexane 36.99 36.76 85.01 85.58 435.10 429.48 3,3,4-Timethylheptane 37.07 36.76 85.40 85.58 434.10 429.48 3-Methyl-4-ethylheptane 37.66 37.87 85.97 86.18 438.00 439.38 4,5-Dimethyloctane 37.87 37.87 87.02 86.18 435.15 439.38 3,4,5-Trimethylheptane 37.45 37.42 85.99 85.28 435.50 438.74 3,4-Dimethyloctane 38.03 37.87 87.15 86.18 436.40 439.38 4-Methyl-3-ethylheptane 37.74 37.87 86.16 86.18 438.00 439.38 2,3-Dimethyl-3-ethylhexane -- 36.76 -- 85.58 439.00 429.48 3,4-Diethylhexane -- 37.87 -- 86.18 436.90 439.38 3-Methyl-3-ethylheptane 37.53 37.11 85.92 86.48 436.80 429.10 2,3-Dimethyloctane 38.20 37.87 87.35 86.18 437.30 439.38 4-Ethyloctane 38.91 38.12 89.09 87.08 436.70 437.80 2,3,3,4-Tetramethylhexane 36.99 36.21 84.52 84.68 437.60 427.60 5-Methylnonane 38.14 38.12 87.02 87.08 438.30 437.80 2,2,3,3,4-Pentamethylpentane -- 34.95 -- 84.47 439.10 413.81 3,3-Diethylhexane 37.61 37.11 85.62 86.48 439.30 429.10 3-Ethyloctane 39.24 38.12 89.29 87.08 439.50 437.80 4-Methylnonane 38.51 38.12 87.77 87.08 438.70 437.80 2-Methylnonane 38.23 38.12 86.89 87.08 440.00 437.80 3-Methylnonane 38.26 38.12 86.76 87.08 441.00 437.80 2,3,4-Trimethyl-3-ethylpentane 37.03 36.21 83.66 84.68 442.60 427.60 2,2,3-Trimethyl-3-ethylpentane 36.48 35.60 82.45 84.98 442.50 418.88 2-Methyl-3,3-diethylpentane -- 36.76 -- 85.58 445.00 429.48 n-Decane 38.75 38.19 86.63 87.98 447.30 434.08 Naphthalene 46.34 41.76 94.41 90.32 490.90 462.37 2-Methylnaphthalene 46.28 45.00 90.02 89.54 514.10 502.54 1-Methylnaphthalene 45.82 45.00 88.97 89.54 515.00 502.54 Pentylbenzene 42.27 42.60 88.35 90.36 478.40 471.45 Pentamethylbenzene 44.78 45.69 88.68 88.65 505.00 515.34 1-Undecene 40.88 39.99 87.78 88.28 465.70 453.04 n-Hexylcyclopentane 41.17 40.77 86.49 87.33 476.00 466.83 n-Pentylcyclohexane 40.84 41.35 85.66 86.82 476.70 476.31 4-Methyldecane 40.70 40.37 88.46 87.68 460.10 460.38 2-Methyldecane 40.25 40.37 87.06 87.68 462.30 460.38 n-Undecane 41.20 40.34 87.87 88.58 468.90 455.36 Biphenyl 45.61 46.31 86.20 90.38 529.10 512.39

Acenaphthene 50.90 49.80 92.21 90.29 552.00 551.57 2-Ethylnaphthalene 48.12 47.42 90.61 89.84 531.00 527.77 1,8-Dimethylnaphthalene 48.05 48.23 89.30 89.93 538.00 536.36 2,6-Dimethylnaphthalene 48.75 48.23 90.62 89.93 538.00 536.36 1,3-Dimethylnaphthalene 49.92 48.23 93.13 89.54 536.00 538.69 2,3-Dimethylnaphthalene 50.18 48.23 92.73 89.93 541.15 536.36 1-Ethylnaphthalene 48.02 47.42 90.32 89.84 531.60 527.77 2,7-Dimethylnaphthalene 48.82 48.23 91.04 89.93 536.20 536.36 1,7-Dimethylnaphthalene 49.71 48.23 92.58 89.93 537.00 536.36 1,6-Dimethylnaphthalene 49.71 48.23 92.58 89.54 537.00 538.69 1,4-Dimethylnaphthalene 50.12 48.23 92.64 89.93 541.00 536.36 1,5-Dimethylnaphthalene 49.90 48.23 92.76 89.93 538.00 536.36 Cyclohexylbenzene 47.15 46.36 91.89 89.20 513.10 519.68 1,3-Diisopropylbenzene 41.62 43.84 87.40 88.56 476.20 494.97 1,4-Diisopropylbenzene 42.92 43.84 88.81 89.34 483.30 490.67 1,3,5-Triethylbenzene 44.61 46.47 91.24 89.76 488.90 517.65 Hexylbenzene 44.95 44.99 90.05 90.96 499.10 494.57 Hexamethylbenzene 46.00 47.70 85.66 89.65 537.00 532.04 Bicyclohexyl 44.52 43.75 87.12 85.09 511.00 514.19 1-Dodecene 42.97 42.19 88.27 88.88 486.80 474.66 n-Heptylcyclopentane 43.35 43.06 87.22 87.93 497.00 489.69 n-Hexylcyclohexane 42.84 43.69 86.21 87.42 497.00 499.79 2,2,4,6,6-Pentamethylheptane 39.21 39.97 86.97 85.28 450.80 468.64 n-Dodecane 43.40 42.43 88.70 89.18 489.30 475.82 Fluorene 53.12 50.21 93.51 90.38 568.00 555.48 3-Methylbiphenyl -- 49.55 -- 90.00 545.70 550.57 Diphenylmethane 49.94 48.47 93.35 90.30 535.00 536.79 2-Isopropylnaphthalene 47.87 48.93 88.45 89.54 541.20 546.44 2,3,5-Trimethylnaphthalene 49.01 51.47 87.84 89.54 558.00 574.84 Heptylbenzene 47.75 47.33 93.08 91.56 513.00 516.86 Dodecahydrofluorene -- 47.03 -- 85.13 533.00 552.40 1-Tridecene 44.98 44.33 88.93 89.48 505.80 495.46 n-Octylcyclopentane 45.40 45.30 87.84 88.53 516.85 511.69 n-Heptylcyclohexane 44.89 45.98 86.84 88.02 517.00 522.39 2,4-Dimethylundecane -- 44.74 -- 87.98 502.10 508.48 2,3-Dimethylundecane -- 44.74 -- 87.98 501.15 508.48 2-Methyldodecane -- 44.71 -- 88.88 502.65 502.99 n-Tridecane 45.65 44.48 89.79 89.78 508.40 495.48 Anthracene -- 54.02 -- 91.16 612.90 592.60 Phenanthrene 54.04 54.02 88.15 90.77 613.00 595.13

1,1-Diphenylethane -- 44.42 -- 90.00 542.00 493.62 1,2,3,4,5,6,7,8-Octahydroanthracene 50.37 45.06 88.84 89.35 567.00 504.31 Octylbenzene 48.92 49.62 91.02 92.16 537.50 538.34 1,2-Dicyclohexylethane 48.29 48.76 88.52 86.29 545.50 565.12 1,1-Dicyclohexylethane 48.16 48.12 88.53 85.39 544.00 563.56 1-Tetradecene 46.90 46.43 92.69 90.08 506.00 515.45 n-Nonylcyclopentane 47.24 47.49 88.26 89.13 535.26 532.87 Cyclohexane,octyl- 46.82 48.22 87.19 88.62 537.00 544.16 n-Tetradecane 47.61 46.49 90.43 90.38 526.50 514.34 1-Methylphenanthrene 56.23 57.26 89.65 90.38 627.15 633.50 2-Methylanthracene -- 57.26 -- 90.77 632.00 630.79 1-Methylanthracene -- 57.26 -- 90.38 636.00 633.50 3-Methylphenanthrene 55.83 57.26 89.62 90.38 623.00 633.50 Benzene,nonyl- 51.57 51.86 93.17 92.76 553.50 559.03 1-Pentadecene 48.66 48.48 89.88 90.68 541.40 534.65 n-Decylcyclopentane 49.00 49.64 88.77 89.73 552.00 553.22 n-Nonylcyclohexane 48.62 50.42 87.60 89.22 555.00 565.09 n-Pentadecane 49.45 48.44 90.97 90.98 543.60 532.42 Pyrene -- 58.25 -- 91.88 677.00 633.97 Fluoranthene -- 57.55 -- 91.10 657.00 631.72 1,2,3,6,7,8-Hexahydropyrene 51.90 51.47 89.04 90.87 582.82 566.43 Benzene,1,1'-butylidenebis- 49.43 49.44 88.27 91.20 560.00 542.08 Benzene, decyl- -- 54.05 -- 93.36 571.04 578.94 1-Hexadecene 50.42 50.48 90.36 90.68 558.00 556.73 n-Decylcyclohexane 50.38 52.56 89.96 89.82 560.00 585.20 Nonane,2,2,4,4,6,8,8-heptamethyl- 45.76 48.05 88.08 86.18 519.50 557.50 n-Hexadecane 51.21 50.35 91.48 91.58 559.80 549.75 2,3-Benzofluorene 60.84 62.47 90.27 90.72 674.00 688.60 1-Methylpyrene 61.73 61.49 90.36 90.72 683.15 677.80 Benzo(a)fluorene 61.24 62.47 90.32 90.72 678.00 688.60 n-Undecylbenzene 56.06 56.20 95.17 93.96 589.00 598.08 1-Heptadecene 53.56 52.44 93.46 91.88 573.00 570.72 n-Undecylcyclohexane 52.05 54.66 90.68 90.42 574.00 604.52 n-Heptadecane 52.89 52.20 91.98 92.18 575.00 566.33 Chrysene 68.90 66.28 95.56 91.40 721.00 725.17 Benz(a)anthracene 64.50 66.28 90.74 91.01 710.80 728.27 Triphenylene 63.21 66.28 90.56 92.01 698.00 720.32 Benzo(c)phenanthrene -- 66.28 -- 91.40 721.00 725.17 p-Terphenyl 63.43 63.12 95.79 91.31 662.20 691.31 1,6-Diphenylhexane -- 59.63 -- 93.30 618.82 639.11

Dodecylbenzene 56.80 58.30 94.50 94.56 601.00 616.47 1-Octadecene 54.27 54.34 92.30 92.48 588.00 587.63 n-Dodecylcyclohexane 53.56 56.71 91.08 91.02 588.00 623.06 n-Octadecane 54.46 54.01 92.41 92.78 589.30 582.17 Tridecylbenzene 57.42 60.35 92.75 95.16 619.00 634.13 1-Nonadecene 57.54 56.20 95.57 93.08 602.00 603.80 Tridecylcyclohexane 55.10 58.71 89.02 91.62 619.00 640.83 n-Nonadecane 56.02 55.78 92.92 93.38 602.90 597.30 Benzo(k)fluoranthene 68.67 69.81 91.19 91.66 753.00 761.62 Benzo(a)pyrene -- 70.51 -- 91.27 768.00 772.51 Eicosane 57.49 57.49 93.33 93.98 616.00 611.73 Heneicosane -- 59.16 -- 94.58 629.70 625.46 Indeno[1,2,3-cd]pyrene 74.26 74.04 91.79 91.51 809.00 809.09 Dibenz(a,h)anthracene -- 78.54 -- 91.90 797.00 854.62 Docosane -- 60.77 -- 95.18 641.80 638.52 Tricosane -- 62.34 -- 95.78 653.20 650.91 Tetracosane -- 63.87 -- 96.38 664.50 662.65 n-Pentacosane -- 65.34 -- 96.98 675.10 673.75 Hexacosane -- 66.77 -- 97.58 685.20 684.22 n-Heptacosane -- 68.14 -- 98.18 695.00 694.07 Octacosane -- 69.47 -- 98.78 704.60 703.32 n-Nonacosane -- 70.76 -- 99.38 714.00 711.97 Tricontane -- 71.99 -- 99.98 722.90 720.04 Dotriacontane -- 74.31 -- 101.18 740.20 734.47 n-Pentatriacotane -- 77.44 -- 102.98 763.20 751.99

SI Table 2. Experimental and calculated values of total heat of melting, entropy of melting and melting point

Compound ΔHm(kJ/mole) ΔSm(J/K mole) Tm(K) Exp Calc Exp Calc Exp Calc Ethyne 6.30 6.30 37.30 31.90 192.30 197.52 Ethene 3.35 2.74 32.21 31.90 104.00 85.97 Ethane 2.86 2.37 31.81 31.90 89.90 74.18 Propadiene 4.40 4.22 32.16 31.90 136.80 132.31 Propyne -- 7.78 -- 43.54 170.20 178.57 Propylene 3.00 4.82 34.09 43.54 88.20 110.77 Cyclopropane 5.44 3.96 37.36 41.07 145.60 96.34 Propane 3.52 4.27 41.17 40.85 85.50 104.59 2-Methylpropane 4.56 4.60 40.11 39.27 113.70 117.04 n-Butane 6.73 6.18 53.62 51.47 134.80 120.03 1,3-Butadiene 7.98 5.54 48.61 40.85 164.20 135.63 1-Butyne 6.03 6.03 40.89 43.54 147.40 138.49 1,2-Butadiene 6.96 6.30 50.84 43.54 136.90 144.72 2-Butyne 9.25 9.25 38.33 31.90 240.90 290.01 2-Methylpropene 5.92 6.24 44.71 40.85 132.40 152.70 1-Butene 3.85 4.91 43.85 47.51 87.80 103.25 trans-2-Butene 9.76 6.90 58.23 40.85 167.60 169.03 cis-2-Butene 7.31 6.90 54.55 40.85 134.00 169.03 Cyclobutane 6.80 5.28 45.13 41.13 182.40 128.26 1,3-Cyclopentadiene 8.01 5.21 45.36 47.44 176.60 109.85 3-Methyl-1-butene 5.36 3.86 51.19 43.54 104.70 88.63 1-Pentene 5.81 6.81 53.85 55.44 107.90 122.86 2-Methyl-1-butene 7.91 6.32 58.38 47.51 135.50 133.02 trans-2-Pentene 8.35 6.99 62.83 51.47 132.90 135.73 cis-2-Pentene 7.11 6.99 58.37 51.47 121.80 135.73 2-Methyl-2-butene 7.60 8.32 54.52 43.54 139.40 191.04 1,1-Dimethylcyclopropane -- 4.49 -- 45.35 164.00 98.91 Cyclopentane 5.84 6.60 45.96 41.18 179.20 160.15 2,2-Dimethylpropane 5.84 4.65 31.10 31.90 256.60 145.69 2-Methylbutane 5.13 6.50 45.24 47.51 113.40 136.87 n-Pentane 8.40 8.08 58.55 59.40 143.47 136.09 1,4-Pentadiene 6.14 7.48 49.44 51.47 124.20 145.35 2-Methyl-1,3-butadiene 4.92 4.92 38.66 43.54 127.27 113.02 1-Pentyne -- 7.94 -- 51.47 183.00 154.19 3-Methyl-1,2-butadiene 7.95 7.72 49.87 43.54 159.40 177.19

1,trans-3-Pentadiene 7.14 7.62 38.47 47.51 185.60 160.43 cis-1,3-Pentadiene 5.64 7.62 42.60 47.51 132.40 160.43 1,2-Pentadiene 7.56 6.38 55.63 47.51 135.90 134.36 2,3-Pentadiene 6.13 8.38 41.56 40.85 147.50 205.21 2-Pentyne -- 7.51 -- 43.54 163.70 172.37 Methylenecyclobutane 5.86 5.86 42.31 46.52 138.50 125.94 Cyclopentene 3.84 5.90 29.53 47.44 138.10 124.44 Spiropentane 6.43 6.43 38.71 44.74 166.10 143.67 1,5-Hexadiene -- 7.44 -- 59.40 132.30 125.32 2,3-Dimethyl-1,3-butadiene -- 8.90 -- 40.85 197.00 217.99 trans-1,3-Hexadiene -- 7.70 -- 55.44 170.60 138.96 trans-2,4-Hexadiene -- 9.70 -- 48.78 228.10 198.91 1-Hexyne -- 9.84 -- 59.40 141.10 165.69 1-Methylcyclopentene -- 7.25 -- 50.13 146.50 144.54 Cyclohexene 7.51 7.22 49.85 50.88 169.50 141.95 3,3-Dimethyl-1-butene 5.44 4.34 41.72 43.54 158.40 99.70 3-Methyl-1-pentene 3.60 5.77 30.35 51.47 118.60 112.01 4-Methyl-1-pentene 4.93 7.14 41.29 51.47 119.40 138.62 2,3-Dimethyl-1-butene 5.45 5.27 47.09 43.54 115.70 121.11 cis-4-Methyl-2-pentene 7.36 5.94 53.25 47.51 138.30 125.04 trans-4-methyl-2-pentene 7.16 5.94 54.06 47.51 132.35 125.04 2-Methyl-1-pentene 7.03 8.23 51.16 55.44 137.40 148.37 1-Hexene 9.35 8.72 70.09 63.37 133.40 137.57 2-Ethyl-1-butene 7.57 6.40 53.52 55.44 141.50 115.47 cis-3-Methyl-2-pentene 5.92 8.40 42.84 51.47 138.20 163.20 2-Methyl-2-pentene 8.03 8.40 58.21 51.47 138.00 163.20 cis-3-Hexene 8.25 7.07 60.94 59.40 135.33 118.99 trans-3-Hexene 11.08 7.07 69.37 59.40 159.73 118.99 trans-2-Hexene 8.26 8.89 58.89 59.40 140.17 149.70 cis-2-Hexene 8.88 8.89 67.27 59.40 132.00 149.70 trans-3-Methyl-2-pentene 7.70 8.40 57.16 51.47 134.70 163.20 2,3-Dimethyl-2-butene 9.97 9.73 50.25 40.85 198.40 238.26 Ethylcyclobutane -- 7.88 -- 53.18 130.10 148.21 Methylcyclopentane 6.93 7.30 53.02 50.13 130.70 145.52 Cyclohexane 9.42 7.91 45.77 43.91 279.80 180.22 2,2-Dimethylbutane 6.26 6.55 45.88 47.51 174.00 137.94 2,3-Dimethylbutane 6.43 6.83 52.96 43.54 144.20 156.78 2-Methylpentane 6.27 8.41 52.42 55.44 119.60 151.67 3-Methylpentane 5.31 8.41 48.23 55.44 110.10 151.67 n-Hexane 13.10 9.99 73.68 67.33 177.80 148.37

Benzene 9.87 8.32 35.40 41.01 278.70 202.93 1,3,5-Hexatriene -- 9.41 -- 51.47 261.00 182.82 1,4-Cyclohexadiene 6.54 6.53 29.76 41.22 223.80 158.42 1,3-Cyclohexadiene 4.20 6.53 26.09 41.22 161.00 158.42 1,6Heptadiene -- 9.35 -- 67.33 144.00 138.87 1-Heptyne -- 11.75 -- 67.33 192.00 174.48 4-Methylcyclohex-1-ene 6.63 7.92 43.16 50.88 153.60 155.71 3-Ethylcyclopentene -- 8.51 -- 54.10 146.00 157.29 (dl)-1,5-Dimethylcyclopentene -- 7.95 -- 50.13 155.00 158.50 1,2-Dimethylcyclopentene -- 8.59 -- 47.44 182.60 181.06 1-Ethylcyclopentene -- 7.33 -- 54.10 154.50 135.46 1-Methylcyclohexene -- 8.57 50.00 50.88 152.60 168.34 Cycloheptene 6.96 8.54 42.20 48.82 217.00 174.97 Methylenecyclohexane -- 8.50 -- 50.88 166.30 167.01 trans-2-Heptene -- 10.80 -- 67.33 163.50 160.37 4,4-Dimethylpent-1-ene 6.28 7.19 46.02 51.47 136.40 139.62 3,3-Dimethylpent-1-ene 7.53 6.25 54.30 51.47 138.70 121.37 trans-4,4-Dimethylpent-2-ene 6.70 6.42 48.66 47.51 137.60 135.19 2,3,3-Trimethyl-1-butene -- 5.76 -- 43.54 163.10 132.18 cis-4,4-Dimethylpent-2-ene 5.86 6.42 42.57 47.51 137.60 135.19 2,4-Dimethylpent-1-ene 8.79 8.55 58.94 51.47 149.09 166.10 2,4-Dimethylpent-2-ene 6.70 7.35 46.08 47.51 145.30 154.80 2,3-Dimethyl-1-pentene 7.11 7.18 51.29 51.47 138.70 139.48 3-Ethyl-1-pentene 5.82 7.67 40.00 59.40 145.50 129.14 5-Methyl-1-hexene 9.08 9.04 59.98 59.40 151.39 152.21 trans-2-Methyl-3-hexene 5.44 6.02 41.40 55.44 131.40 108.63 (dl)4-Methyl-1-hexene 7.50 9.04 57.03 59.40 131.50 152.21 4-Methyl-trans-2-hexene 7.11 7.85 48.30 55.44 147.30 141.54 trans-5-Methyl-2-hexene 6.28 9.22 42.21 55.44 148.70 166.25 cis-3,4-Dimethylpent-2-ene 8.79 7.35 55.00 47.51 159.76 154.80 trans-3,4-Dimethylpent-2-ene 8.79 7.35 59.00 47.51 148.92 154.80 2-Methyl-1-hexene 13.00 10.13 76.34 63.37 170.28 159.88 1-Heptene 12.66 10.62 82.58 71.30 153.30 149.00 3-Methyl-trans-3-hexene -- 8.48 -- 59.40 131.60 142.79 2-Methyl-2-hexene 9.21 10.31 64.56 59.40 142.60 173.50 3-Ethyl-2-pentene -- 8.48 -- 59.40 149.00 142.79 trans-3-Heptene 10.50 8.97 76.98 67.33 136.40 133.28 cis-3-Heptene -- 8.97 -- 67.33 136.40 133.28 2,3-dimethylpent-2-ene 8.79 9.81 56.80 51.47 154.70 190.67 cis-3-methyl-2-hexene 11.28 9.70 72.99 59.40 154.50 163.37

cis-2-Heptene -- 10.80 -- 67.33 163.50 160.37 1,1-Dimethylcyclopentane 7.58 7.12 49.52 47.44 203.70 150.16 cis-1,3-Dimethylcyclopentane 7.40 8.00 53.10 50.13 139.30 159.48 (dl)-trans-1,3-Dimethylcyclopentane 7.40 8.00 53.12 47.44 139.30 168.54 (dl)-trans-1,2-Dimethylcyclopentane 7.40 8.00 47.55 47.44 155.58 168.54 cis-1,2-Dimethylcyclopentane 8.21 8.00 54.56 50.13 219.00 159.48 Ethylcyclopentane 6.87 9.20 51.00 54.10 134.70 170.09 Methylcyclohexane 6.75 8.61 46.04 50.88 146.60 169.31 Cycloheptane 7.60 9.23 47.60 51.51 265.00 179.25 2,2-Dimethylpentane 5.86 8.46 39.57 55.44 148.10 152.59 2,2,3-Trimethylbutane 4.58 6.88 28.53 40.85 248.00 168.36 2,4-Dimethylpentane 6.85 8.73 44.48 51.47 154.00 169.65 3,3-Dimethylpentane 7.07 8.46 51.19 55.44 138.10 152.59 (dl)2,3-Dimethylpentane -- 8.73 -- 51.47 149.00 169.65 2-Methylhexane 9.18 10.31 59.30 63.37 154.80 162.77 (dl)3-Methylhexane -- 10.31 -- 63.37 154.00 162.77 3-Ethylpentane 9.55 10.31 61.77 63.37 154.60 162.77 n-Heptane 14.04 13.99 76.97 77.64 182.40 180.19 Toluene 6.62 9.94 37.17 47.97 178.10 207.18 Cycloheptatriene 3.51 7.16 21.10 48.82 193.50 146.61 Ethylbenzene 9.18 10.02 51.54 54.63 178.10 183.42 1,4-Dimethylbenzene 17.11 11.56 59.74 45.28 286.40 255.22 1,3-Dimethylbenzene 11.57 11.56 51.35 47.97 225.30 240.88 1,2-Dimethylbenzene 13.60 11.56 54.88 47.97 247.80 240.88 (dl)-4-Vinyl-1-cyclohexene -- 9.78 -- 50.88 164.10 192.17 cis-1,5-Cyclooctadiene -- 9.17 -- 49.36 203.00 185.73 1-Octyne -- 13.65 -- 75.26 193.70 181.42 4-Octyne -- 9.57 -- 67.33 172.00 142.17 3-Octyne -- 9.57 -- 67.33 169.10 142.17 2-Octyne -- 13.22 -- 67.33 211.40 196.39 Allylcyclopentane -- 9.83 -- 58.06 162.30 169.37 Vinylcyclohexane -- 10.47 -- 50.88 146.40 205.77 Ethylidenecyclohexane -- 10.58 -- 50.88 180.30 207.91 Cyclooctene 11.61 9.86 58.53 52.06 259.20 189.41 cis-Bicyclo[3.3.0]octane -- 10.17 -- 49.36 224.00 205.99 2,4,4-Trimethyl-1-pentene 8.77 8.60 48.86 51.47 179.50 167.09 trans-2,2-Dimethyl-3-hexene -- 6.50 -- 55.44 135.60 117.33 trans-2,5-Dimethyl-3-hexene -- 4.98 -- 48.78 177.90 102.02 2,4,4-Trimethyl-2-pentene 6.80 7.84 40.79 47.51 166.70 164.95 cis-2,2-Dimethyl-3-hexene -- 6.50 -- 55.44 135.60 117.33

2,3,3-Trimethyl-1-pentene -- 7.66 -- 51.47 204.00 148.84 3-Ethyl-2-methyl-1-pentene -- 9.09 -- 59.40 160.10 152.95 2-Methyl-trans-3-heptene -- 7.93 -- 63.37 165.50 125.12 2,3,4-Trimethyl-2-pentene -- 8.77 -- 47.51 159.60 184.57 2-Methyl-1-heptene -- 12.04 -- 71.30 183.00 168.83 1-Octene 15.31 12.53 89.27 79.23 171.50 158.14 2,3-Dimethyl-2-hexene -- 11.72 -- 59.40 157.90 197.31 trans-4-Octene -- 10.88 -- 75.26 179.20 144.57 2-Methyl-2-heptene -- 12.21 -- 67.33 151.00 181.38 cis-3-Octene -- 10.88 -- 75.26 147.00 144.57 cis-4-Octene -- 10.88 -- 75.26 155.00 144.57 trans-2-Octene -- 12.70 -- 75.26 185.30 168.80 tran-3-Octene -- 10.88 -- 75.26 163.00 144.57 cis-2-Octene -- 12.70 -- 75.26 172.00 168.80 cis-1,3-Dimethylcyclohexane 10.82 9.31 54.77 50.88 197.60 183.07 trans-1,3-Dimethylcyclohexane 9.87 9.31 53.90 50.88 183.10 183.07 cis-1,4-Dimethylcyclohexane 9.31 9.31 50.11 50.88 185.70 183.07 trans-1,4-Dimethylcyclohexane 12.33 9.31 52.20 48.18 236.20 193.30 1,1,3-Trimethylcyclopentane -- 7.82 -- 50.13 130.60 156.05 1,2(cis),3(trans)-trimethylcyclopentane -- 8.70 -- 50.13 160.25 173.44 1,1,2-Trimethylcyclopentane -- 7.82 -- 50.13 251.40 156.05 1,cis-2,cis-4-Trimethylcyclopentane -- 8.70 -- 50.13 140.83 173.44 1,cis-2,trans-4-Trimethylcyclopentane -- 8.70 -- 50.13 139.00 173.44 1-Ethyl-1-methylcyclopentane -- 9.03 -- 54.10 129.20 166.91 1,cis-2,cis-3-Trimethylcyclopentane -- 8.70 -- 50.13 156.70 173.44 Isopropylcyclopentane -- 9.53 -- 50.13 161.60 190.00 (dl)-cis-1-Ethyl-2-methylcyclopentane -- 9.90 -- 54.10 167.10 183.03 Propylcyclopentane 10.03 11.11 64.42 62.03 155.70 179.07 1,trans-2-Dimethylcyclohexane 10.50 9.31 56.76 50.88 185.00 183.07 1,1-Dimethylcyclohexane 7.99 8.44 47.42 50.88 239.80 165.93 cis-1,2-Dimethylcyclohexane -- 9.31 55.22 50.88 221.00 183.07 Ethylcyclohexane 8.33 10.52 51.52 54.84 161.70 191.82 Cyclooctane 9.21 10.55 48.89 46.67 287.80 226.11 3-Ethyl-2-methylpentane 11.34 10.64 71.73 59.40 158.10 179.09 2,2,4-Trimethylpentane 9.04 8.78 54.52 51.47 165.80 170.64 2,2,3,3-Tetramethylbutane 9.54 6.93 33.28 33.88 373.90 204.48 2,2-Dimethylhexane 6.78 10.37 44.62 63.37 151.90 163.58 2,5-Dimethylhexane 12.95 10.64 71.18 59.40 182.00 179.09 2,2,3-Trimethylpentane 8.62 8.78 53.60 51.47 160.80 170.64 3,3-Dimethylhexane 7.11 10.37 48.42 63.37 146.90 163.58

2,3,4-Trimethylpentane 9.27 9.06 56.59 47.51 163.80 190.63 2,3,3-Trimethylpentane -- 8.78 -- 51.47 172.10 170.64 2-Methylheptane 11.92 12.22 72.68 71.30 164.00 171.40 4-Methylheptane 10.84 12.22 71.32 71.30 152.00 171.40 3-Ethyl-3-methylpentane 10.80 10.37 59.31 63.37 182.10 163.58 3-Methylheptane 11.70 12.22 76.67 71.30 152.60 171.40 n-Octane 20.74 17.99 95.93 87.95 216.20 204.55 Styrene 10.96 10.92 45.29 50.67 242.00 215.60 Cyclooctatetraene 11.27 7.78 41.97 43.97 268.50 177.02 a-Methylstyrene 11.92 12.61 47.72 50.67 249.80 248.80 trans-Methylstyrene -- 13.01 -- 54.63 243.70 238.04 Indane 9.38 11.94 49.34 55.17 221.80 216.49 Isopropylbenzene 7.32 8.98 41.36 50.67 177.00 177.13 Propylbenzene 9.27 11.93 53.43 62.56 173.50 190.64 4-Ethyltoluene 12.70 11.64 60.28 54.63 210.70 213.02 2-Ethyltoluene 9.96 11.64 51.82 54.63 192.20 213.02 1,3,5-Trimethylbenzene 9.51 13.17 42.27 43.70 225.00 301.42 1,2,3-Trimethylbenzene 10.17 13.17 41.81 47.97 247.80 274.59 1,2,4-Trimethylbenzene 12.65 13.17 55.34 50.67 228.60 259.99 1-Nonyne -- 17.65 -- 85.57 223.00 206.31 trans-Hexahydroindan 10.90 11.49 50.97 52.54 213.86 218.64 cis-Hexahydroindan 10.05 11.49 53.37 52.54 236.50 218.64 1-Nonene 19.97 16.53 104.17 89.53 191.70 184.61 1,1,3-Trimethylcyclohexane -- 9.14 50.00 50.88 207.30 179.68 Propylcyclohexane 10.37 12.43 58.16 62.77 178.30 197.95 Isopropylcyclohexane -- 10.84 -- 50.88 183.60 213.14 Butylcyclopentane 11.31 13.01 68.46 69.96 165.20 186.02 2,2,4,4-Tetramethylpentane 9.75 8.83 47.22 51.47 206.50 171.63 2,2,5-Trimethylhexane -- 10.69 -- 59.40 167.30 179.95 2,2,4-Trimethylhexane 11.00 10.69 71.90 59.40 153.00 179.95 2,3,5-Trimethylhexane 10.00 10.96 68.92 55.44 145.10 197.75 2,4,4-Trimethylhexane 11.30 10.69 70.80 59.40 159.60 179.95 2,2-Dimethylheptane -- 12.27 -- 71.30 160.00 172.12 2,2,3,4-Tetramethylpentane -- 9.11 -- 47.51 152.00 191.71 2,4-Dimethylheptane 12.00 12.54 75.00 67.33 160.00 186.31 2,2-Dimethyl-3-ethylpentane 10.20 10.69 58.72 59.40 173.70 179.95 2,2,3-Trimethylhexane 10.30 10.69 67.25 59.40 153.16 179.95 4,4-Dimethylheptane 10.10 12.27 59.32 71.30 170.26 172.12 2,6-Dimethylheptane 13.00 12.54 76.43 67.33 170.10 186.31 3,5-Dimethylheptane 13.00 12.54 76.35 67.33 170.26 186.31

2,5-Dimethylheptane 12.00 12.54 74.93 67.33 160.16 186.31 2,4-Dimethyl-3-ethylpentane 7.20 10.96 47.81 55.44 150.60 197.75 2,3,3-Trimethylhexane 9.10 10.69 58.26 59.40 156.20 179.95 2,3,4-Trimethylhexane 10.70 10.96 68.43 55.44 156.36 197.75 2,2,3,3-Tetramethylpentane 9.66 8.83 50.90 51.47 263.20 171.63 3-Methyl-4-ethylhexane 12.30 12.54 76.80 67.33 160.16 186.31 3,3,4-Trimethylhexane 8.10 10.69 47.15 59.40 171.80 179.95 2,3-Dimethylheptane 14.00 12.54 89.17 67.33 157.00 186.31 3,4-Dimethylheptane 13.00 12.54 76.47 67.33 170.00 186.31 4-Ethylheptane 15.00 16.22 93.77 81.60 159.96 198.76 2,3,3,4-Tetramethylpentane -- 9.11 -- 47.51 170.90 191.71 4-Methyloctane 16.00 16.22 100.06 81.60 159.90 198.76 3-Ethylheptane -- 16.22 -- 81.60 158.10 198.76 2-Methyloctane 18.00 16.22 93.41 81.60 192.70 198.76 3-Methyloctane 17.00 16.22 102.78 81.60 165.40 198.76 2,3-Dimethyl-3-ethylpentane 11.00 10.69 63.34 59.40 173.67 179.95 3,3-Diethylpentane 11.38 12.27 48.20 71.30 240.10 172.12 n-Nonane 21.75 21.99 99.20 98.26 219.50 223.80 Indene 10.20 11.25 37.54 52.47 271.70 214.42 Benzene, 1-ethenyl-2-methyl- -- 12.54 -- 54.63 205.00 229.50 1,4-Dihydronaphthalene -- 12.57 -- 53.65 298.00 234.29 1,2,3,4-Tetrahydronaphthalene 12.45 13.26 52.47 56.35 237.30 235.37 1,3-Dimethyl-4-ethylbenzene 12.93 13.26 61.54 54.63 210.10 242.62 1,2,3,5-Tetramethylbenzene 12.93 14.79 51.87 47.97 249.30 308.29 tert-Butylbenzene 8.40 9.46 39.03 50.67 215.20 186.65 Isobutylbenzene 12.51 12.25 56.45 58.60 221.60 209.07 (dl)-sec-Butylbenzene 9.83 10.88 49.66 58.60 198.00 185.69 3-Isopropyltoluene 13.68 10.59 65.37 50.67 209.30 209.05 4-Isopropyltoluene 9.67 10.59 47.36 50.67 204.20 209.05 2-Isopropyltoluene 10.00 10.59 49.59 50.67 201.64 209.05 1,3-Diethylbenzene 10.97 11.72 57.99 62.56 189.10 187.33 3-Propyltoluene 10.59 13.54 55.57 62.56 190.50 216.49 4-Propyltoluene 11.51 13.54 54.95 62.56 209.40 216.49 1,2-Diethylbenzene 16.78 11.72 69.39 62.56 241.80 187.33 Butylbenzene 11.22 13.83 60.55 70.49 185.30 196.23 1,3-Dimethyl-5-ethylbenzene 8.95 13.26 47.45 54.63 188.70 242.62 1,4-Diethylbenzene 10.59 11.72 45.99 62.56 230.17 187.33 2-Propyltoluene 14.77 13.54 69.45 62.56 212.70 216.49 1,4-Dimethyl-2-ethylbenzene 15.19 13.26 69.27 54.63 219.30 242.62 1,2-Dimethyl-4-ethylbenzene 12.05 13.26 58.47 54.63 206.10 242.62

1,3-Dimethyl-2-ethylbenzene 14.71 13.26 57.28 54.63 256.80 242.62 1,2-Dimethyl-3-ethylbenzene 13.64 13.26 61.03 54.63 223.50 242.62 1,2,3,4-Tetramethylbenzene 11.23 14.79 42.31 47.97 265.40 308.29 1,2,4,5-Tetramethylbenzene 20.88 14.79 59.30 45.28 352.60 326.64 (d)-Limonene -- 12.53 57.13 50.88 198.65 246.35 (dl)-Limonene -- 12.53 -- 50.88 181.00 246.35 a-Pinene -- 10.03 50.00 51.51 211.00 194.68 Decalin 14.41 12.81 59.37 47.58 242.70 269.14 trans-Bicyclo[4.4.0]decane 11.62 12.81 51.09 50.28 242.40 254.72 cis-Bicyclo[4.4.0]decane 14.43 12.81 59.46 50.28 242.70 254.72 1-Decene 21.76 20.53 106.80 99.84 207.00 205.61 n-Pentylcyclopentane -- 14.92 -- 77.89 190.00 191.55 tert-Butylcyclohexane -- 10.90 -- 50.88 231.80 214.14 1-Isopropyl-4-methylcyclohexane -- 11.54 -- 50.88 183.10 226.90 Isobutylcyclohexane -- 12.75 -- 58.81 178.00 216.81 Butylcyclohexane 14.14 14.33 71.27 70.70 198.40 202.71 2,2,5,5-Tetramethylhexane 9.80 10.74 37.98 56.71 258.00 189.40 2,2-Dimethyl-4-ethylhexane 15.00 12.60 68.49 67.33 219.00 187.06 2,2,4,5-Tetramethylhexane 14.00 11.01 63.93 55.44 219.00 198.67 2,2,3,5-Tetramethylhexane 10.00 11.01 45.66 55.44 219.00 198.67 2,4,6-Trimethylheptane 11.00 12.87 50.23 63.37 219.00 203.08 2,2,6-Trimethylheptane -- 12.60 -- 67.33 168.00 187.06 2,3,3,5-Tetramethylhexane 15.00 11.01 57.57 55.44 260.56 198.67 2,5,5-Trimethylheptane 11.00 12.60 50.23 67.33 219.00 187.06 2,2,4,4-Tetramethylhexane 13.00 10.74 59.36 59.40 219.00 180.81 2,5-Dimethyl-3-ethylhexane 13.00 12.87 59.36 63.37 219.00 203.08 2,3,4,5-Tetramethylhexane 12.00 11.29 46.05 51.47 260.56 219.27 2,2-Dimethyl-3-ethylhexane 14.00 12.60 63.93 67.33 219.00 187.06 3,3,5-Trimethylheptane 14.00 12.60 63.93 67.33 219.00 187.06 2-Methyl-4-ethylheptane 15.00 14.45 68.49 75.26 219.00 192.00 2,4-Dimethyloctane 16.00 14.45 73.01 75.26 219.16 192.00 2,4-Dimethyl-3-isopropylpentane -- 11.29 -- 51.47 191.30 219.27 4-Propylheptane 18.00 20.22 82.19 91.91 219.00 219.99 2,2,3,4,4-Pentamethylpentane -- 9.16 -- 47.51 234.30 192.78 4-Isopropylheptane 16.00 14.45 73.06 75.26 219.00 192.00 3,5-Dimethyloctane 15.00 14.45 68.44 75.26 219.16 192.00 2,5-Dimethyloctane 16.00 14.45 73.01 75.26 219.16 192.00 2,6-Dimethyloctane 16.00 14.45 73.01 75.26 219.16 192.00 2,2,3,3-Tetramethylhexane 12.40 10.74 56.62 59.40 219.00 180.81 2,4-Dimethyl-3-ethylhexane 10.00 12.87 45.66 63.37 219.00 203.08

2,7-Dimethyloctane 17.30 14.45 79.32 75.26 218.10 192.00 2-Methyl-5-ethylheptane 15.00 14.45 68.49 75.26 219.00 192.00 2,4-Dimethyl-4-ethylhexane 15.00 12.60 68.49 67.33 219.00 187.06 3,4,4-Trimethylheptane 12.00 12.60 54.79 67.33 219.00 187.06 2,3-Dimethyl-4-ethylhexane 14.00 12.87 63.93 63.37 219.00 203.08 3,6-Dimethyloctane 15.00 14.45 68.44 75.26 219.16 192.00 2-Methyl-3-ethylheptane 17.00 14.45 77.63 75.26 219.00 192.00 3,3-Dimethyloctane 16.00 16.27 73.01 81.60 219.16 199.39 2,3,4,4-Tetramethylhexane 9.00 11.01 34.54 55.44 260.56 198.67 3,3-Dimethyl-4-ethylhexane 13.00 12.60 59.36 67.33 219.00 187.06 3,4-Dimethyl-3-ethylhexane 13.00 12.60 59.36 67.33 219.00 187.06 3-Methyl-4-ethylheptane 16.00 14.45 73.06 75.26 219.00 192.00 4,5-Dimethyloctane 16.00 14.45 73.06 75.26 219.00 192.00 3,4,5-Trimethylheptane 14.00 12.87 63.93 63.37 219.00 203.08 3,4-Dimethyloctane 17.00 14.45 77.57 75.26 219.16 192.00 2,3-Dimethyl-3-ethylhexane 14.00 12.60 63.93 67.33 219.00 187.06 3,4-Diethylhexane 15.00 14.45 68.49 75.26 219.00 192.00 3-Methyl-3-ethylheptane 15.00 16.27 68.49 81.60 219.00 199.39 2,3,3,4-Tetramethylhexane 12.00 11.01 46.05 55.44 260.56 198.67 5-Methylnonane 16.65 20.22 89.18 91.91 186.70 219.99 2,2,3,3,4-Pentamethylpentane -- 9.16 -- 44.81 236.60 204.37 3,3-Diethylhexane 15.00 16.27 68.49 81.60 219.00 199.39 2-Methyl-3-isopropylhexane 11.00 12.87 50.19 63.37 219.16 203.08 4-Methylnonane 15.19 20.22 86.94 91.91 174.70 219.99 2-Methylnonane 17.49 20.22 87.98 91.91 198.80 219.99 3-Methylnonane 18.70 20.22 99.19 91.91 188.50 219.99 3,3,4,4-Tetramethylhexane 10.00 10.74 38.38 56.71 260.56 189.40 2,2,3-Trimethyl-3-ethylpentane -- 10.74 -- 59.40 230.50 180.81 n-Decane 28.70 25.99 117.96 108.57 243.30 239.39 Naphthalene 19.10 14.05 54.05 47.31 353.40 297.01 2-Methylnaphthalene 17.74 15.67 58.86 52.70 307.20 297.32 1-Methylnaphthalene 11.93 15.67 49.31 52.70 242.70 297.32 Pentylbenzene 15.24 15.74 76.97 78.42 198.00 200.69 Pentamethylbenzene 11.65 16.41 39.33 47.97 327.50 342.00 1-Undecene 26.19 24.53 118.20 110.15 224.00 222.68 n-Hexylcyclopentane -- 18.92 -- 88.20 200.00 214.51 n-Pentylcyclohexane -- 16.24 -- 78.63 215.50 206.50 4-Methyldecane -- 24.22 -- 102.22 195.50 236.94 2-Methyldecane 25.09 24.22 111.95 102.22 224.10 236.94 n-Undecane 29.04 29.99 118.60 118.88 247.60 252.28

Biphenyl 18.58 20.12 54.33 50.73 342.00 396.52 Acenaphthene 21.46 16.35 58.54 52.84 366.60 309.47 2-Ethylnaphthalene -- 15.75 -- 56.67 265.60 277.97 1,8-Dimethylnaphthalene 15.77 17.29 46.86 50.01 336.30 345.68 2,6-Dimethylnaphthalene 25.06 17.29 65.37 50.01 383.30 345.68 1,3-Dimethylnaphthalene -- 17.29 -- 52.70 267.00 328.01 2,3-Dimethylnaphthalene 15.90 17.29 42.06 50.01 378.00 345.68 1-Ethylnaphthalene 16.30 15.75 62.91 56.67 259.10 277.97 2,7-Dimethylnaphthalene 23.35 17.29 63.32 50.01 368.80 345.68 1,7-Dimethylnaphthalene -- 17.29 -- 50.01 259.10 345.68 1,6-Dimethylnaphthalene -- 17.29 -- 52.70 256.10 328.01 1,5-Dimethylnaphthalene -- 17.29 -- 50.01 355.00 345.68 Cyclohexylbenzene 15.27 15.59 54.44 58.01 280.50 268.68 1,3-Diisopropylbenzene -- 9.63 -- 54.63 209.90 176.23 1,4-Diisopropylbenzene -- 9.63 -- 49.24 256.00 195.51 1,3,5-Triethylbenzene -- 13.42 -- 70.49 206.50 190.36 Hexylbenzene 18.41 17.65 86.84 86.35 212.00 204.34 Hexamethylbenzene 22.39 18.02 51.60 41.01 438.70 439.51 Bicyclohexyl 16.14 14.86 59.13 53.72 277.00 276.67 1-Dodecene 24.42 28.53 104.92 120.46 237.90 236.83 n-Heptylcyclopentane -- 22.92 -- 98.50 212.00 232.67 n-Hexylcyclohexane 22.18 20.24 84.12 88.94 263.60 227.54 2,2,4,6,6-Pentamethylheptane -- 12.97 -- 63.37 206.00 204.69 n-Dodecane 36.82 33.99 139.79 129.18 263.40 263.11 Fluorene 19.58 21.10 50.48 50.73 387.90 415.90 3-Methylbiphenyl -- 21.73 -- 53.43 296.00 406.79 Diphenylmethane 19.05 17.71 63.71 57.39 299.00 308.64 2-Isopropylnaphthalene -- 14.71 -- 52.70 287.50 279.03 2,3,5-Trimethylnaphthalene -- 18.90 -- 52.70 298.65 358.69 Heptylbenzene 21.80 21.65 96.89 96.66 225.00 223.92 1-Tridecene -- 32.53 -- 130.77 250.30 248.75 n-Octylcyclopentane -- 26.92 -- 108.81 228.70 247.39 n-Heptylcyclohexane 22.22 24.24 95.45 99.25 232.80 244.21 2,4-Dimethylundecane -- 26.45 -- 106.19 204.00 249.09 2-Methyldodecane -- 32.22 -- 122.84 246.00 262.29 n-Tridecane 36.15 37.99 136.31 139.49 267.80 272.34 Anthracene 28.83 19.78 58.84 48.65 490.00 406.62 Phenanthrene 18.00 19.78 48.36 51.34 372.20 385.28 1-Methylfluorene -- 22.72 50.00 53.43 358.00 425.19 1,1-Diphenylethane 17.57 17.58 68.89 53.43 255.10 328.96

1,2,3,4,5,6,7,8-Octahydroanthracene 20.85 18.20 60.69 59.18 346.00 307.55 Octylbenzene 29.96 25.65 126.41 106.97 237.00 239.74 1,2-Dicyclohexylethane -- 18.67 -- 69.58 284.50 268.39 1,1-Dicyclohexylethane -- 17.09 -- 57.68 252.00 296.32 1-Tetradecene -- 36.53 -- 141.08 261.00 258.93 cis-1,4-Di-tert-butylcyclohexane 8.79 13.88 29.98 52.15 293.20 266.09 trans-1,4-Di-tert-butylcyclohexane 17.15 13.88 47.22 49.45 363.20 280.58 n-Nonylcyclopentane 33.13 30.92 135.69 119.12 244.16 259.56 Cyclohexane,octyl- 30.13 28.24 119.07 109.56 253.00 257.74 n-Tetradecane 45.07 41.99 161.66 149.80 278.80 280.30 1-Methylphenanthrene -- 21.40 -- 54.04 396.00 396.00 9-Methylanthracene -- 21.40 -- 54.04 354.50 396.00 2-Methylanthracene -- 21.40 -- 51.34 482.00 416.77 1-Methylanthracene -- 21.40 -- 54.04 358.50 396.00 3-Methylphenanthrene -- 21.40 -- 54.04 338.00 396.00 Benzene,nonyl- 28.87 29.65 115.94 117.28 249.00 252.77 Benzene,1,3,5-tris(1-methylethyl)- -- 10.28 -- 58.60 265.60 175.45 1-Pentadecene -- 40.53 -- 151.39 270.20 267.72 n-Decylcyclopentane 33.13 34.92 131.99 129.43 251.00 269.79 n-Nonylcyclohexane -- 32.24 -- 119.87 263.00 268.94 n-Pentadecane 43.77 45.99 156.02 160.11 282.90 287.24 Pyrene 17.65 17.03 43.36 46.49 423.80 366.42 Fluoranthene 18.73 19.89 48.85 51.88 383.36 383.34 1,2,3,6,7,8-Hexahydropyrene 23.11 21.29 57.69 57.34 406.00 371.34 Benzene,1,1'-butylidenebis- -- 21.39 -- 69.29 300.00 308.68 Benzene, decyl- -- 33.65 -- 127.59 258.70 263.70 1-Hexadecene 34.08 40.53 124.39 151.39 277.50 267.72 n-Decylcyclohexane 38.62 36.24 142.30 130.18 271.40 278.37 n-Hexadecane 53.35 49.99 183.27 170.42 291.10 293.33 2,3-Benzofluorene 23.40 26.83 47.78 54.57 489.70 491.65 1-Methylpyrene -- 18.65 -- 54.57 347.65 341.78 Benzo(a)fluorene 22.20 26.83 49.26 54.57 462.80 491.65 n-Undecylbenzene 36.00 37.65 134.33 137.90 268.00 272.99 1-Heptadecene -- 48.53 -- 172.01 284.50 282.14 n-Undecylcyclohexane 42.68 40.24 152.99 140.49 278.96 286.42 n-Heptadecane 51.13 53.99 174.67 180.73 295.10 298.73 Chrysene 29.37 25.51 55.50 52.34 531.40 487.39 Benz(a)anthracene 21.38 25.51 49.26 55.04 434.00 463.53 Triphenylene 24.74 25.51 52.42 48.07 472.00 530.68 Naphthacene -- 25.51 65.12 49.65 613.00 513.84

Benzo(c)phenanthrene 16.32 25.51 48.76 52.34 334.70 487.39 p-Terphenyl 37.46 31.91 83.12 59.00 486.30 540.82 1,6-Diphenylhexane -- 25.30 -- 97.04 270.00 260.72 Dodecylbenzene 40.17 41.65 145.53 148.21 276.00 280.99 1-Octadecene -- 52.53 -- 182.32 290.50 288.12 n-Dodecylcyclohexane 45.84 44.24 160.84 150.80 285.00 293.36 n-Octadecane 60.50 57.99 200.80 191.04 301.30 303.55 Tridecylbenzene 43.93 45.65 155.24 158.52 283.00 287.95 1-Nonadecene -- 56.53 -- 192.62 296.00 293.47 Tridecylcyclohexane 51.05 48.24 175.11 161.10 291.50 299.42 n-Nonadecane 61.07 61.99 202.10 201.35 304.00 307.88 Perylene 31.87 22.76 57.81 50.07 551.29 454.65 Benzo(b)fluoranthene -- 25.62 -- 55.46 441.00 461.90 Benzo(k)fluoranthene 27.50 25.62 56.12 52.76 490.00 485.49 Benzo(a)pyrene 25.81 22.76 57.42 55.46 449.50 410.48 Benzo(e)pyrene 19.08 22.76 42.35 52.76 450.50 431.44 Cholanthrene -- 27.81 50.00 57.88 447.00 480.57 Tetradecylbenzene -- 49.65 -- 168.82 289.00 294.06 Eicosane 67.80 65.99 219.60 211.66 308.80 311.78 3-Methylcholanthrene -- 29.43 50.00 57.88 453.00 508.51 pentadecylbenzene 51.47 53.65 174.38 179.13 295.16 299.47 pentadecylbenzene -- 53.65 -- 179.13 295.16 299.47 Heneicosane 64.12 69.99 206.01 221.97 313.40 315.32 Indeno[1,2,3-cd]pyrene 21.51 22.87 49.43 55.84 435.20 409.55 Benzo(ghi)perylene 17.50 20.02 31.58 50.45 554.20 396.76 Anthanthrene -- 20.02 75.23 50.45 530.90 396.76 Dibenz(a,h)anthracene 31.16 31.24 57.26 53.14 544.20 587.89 Pentacene -- 31.24 69.48 50.45 544.00 619.29 Picene 35.19 31.24 55.23 53.14 637.20 587.89 Benzo[b]chrysene -- 31.24 75.23 53.14 567.00 587.89 Dibenz(a,j)anthracene -- 31.24 75.23 53.14 542.50 587.89 Dibenz(a,c)anthracene 25.82 31.24 46.65 53.14 553.50 587.92 Benzo(a)naphthacene -- 31.24 80.98 55.84 530.00 559.53 Docosane 78.50 73.99 245.00 232.27 317.00 318.55 Tricosane 75.73 77.99 237.70 242.58 320.00 321.50 Dibenzo(a,h)pyrene -- 28.49 77.41 53.49 579.50 532.71 Dibenzo(a,e)pyrene 30.50 28.49 58.63 56.18 520.20 507.17 Dibenzo(a,l)pyrene 24.68 28.49 49.24 56.18 501.20 507.17 Dibenzo(a,i)pyrene 27.87 28.49 50.05 56.18 556.80 507.17 2,11-Dicyclohexyldodecane 44.27 42.95 147.08 134.60 301.00 319.06

1,1-Dicyclohexyldodecane 44.27 48.72 147.26 151.26 300.60 322.08 Tetracosane 86.19 81.99 266.79 252.89 324.00 324.21 n-Pentacosane 83.81 85.99 258.18 263.20 327.00 326.71 Hexacosane 91.70 89.99 289.30 273.51 330.00 329.02 n-Heptacosane 87.59 93.99 265.68 283.82 332.00 331.16 Octacosane 100.08 97.99 300.26 294.13 337.50 333.15 n-Nonacosane 95.82 101.99 286.08 304.44 337.00 335.01 Tricontane 106.32 105.99 315.06 314.75 338.90 336.75 Pentacosane, 13-phenyl- -- 88.60 -- 263.98 305.00 335.62 hentriacontane -- 109.99 -- 325.06 341.05 338.37 Dotriacontane 117.95 113.99 345.11 335.36 343.00 339.90 n-Tritriacontane 110.67 117.99 322.40 345.67 345.00 341.33 Tetratriacontane 126.00 121.99 364.16 355.98 346.00 342.69 n-Pentatriacotane 127.49 125.99 368.05 366.29 348.00 343.96 Hexatriacontane 129.29 129.99 371.13 376.60 349.10 345.17 2-methylpentatriacontane -- 124.22 -- 359.95 343.20 345.11 3-methylpentatriacontane -- 124.22 -- 359.95 339.20 345.11 heptatriacontane -- 133.99 -- 386.91 350.85 346.31 octatriacontane -- 137.99 -- 397.22 352.15 347.39 nonatriacontane -- 141.99 -- 407.53 353.45 348.42 1,8-bis[4-(4'-butylbiphenyl)]octane -- 76.29 -- 189.41 398.00 402.76 Tetracontane 147.46 145.99 418.40 417.84 354.10 349.40 hentetracontane -- 142.37 -- 428.15 357.50 332.52 hentetracontane -- 149.99 -- 428.15 356.00 350.33 dotetracontane -- 153.99 -- 438.45 356.10 351.21 Tritetracontane -- 157.99 -- 448.76 358.00 352.06 Tetratetracontane -- 161.99 -- 459.07 360.90 352.86 22-methyltritetracontane -- 156.22 -- 442.42 339.80 353.10 n-tetratetracontane -- 161.99 -- 459.07 359.20 352.86 pentatetracontane -- 165.99 -- 469.38 360.00 353.64 Hexatetracontane 175.30 169.99 489.40 479.69 360.70 354.37 n-heptatetracontane -- 173.99 -- 490.00 361.20 355.08 n-Octatetracontane -- 177.99 -- 500.31 361.40 355.76 n-nonatetracontane -- 181.99 -- 510.62 363.00 356.41 pentacontane 185.00 185.99 506.85 520.93 366.90 357.04 n-henpentacontane -- 189.99 -- 531.24 366.00 357.64 dopentacontane -- 193.99 -- 541.54 367.00 358.22 n-tripenlacontane -- 197.99 -- 551.85 367.50 358.77 Tetrapentacontane -- 201.99 -- 562.16 368.00 359.31 n-penlapentacontane -- 205.99 -- 572.47 368.00 359.83

n-hexapentacontane -- 209.99 -- 582.78 369.00 360.32 heptapentacontane -- 213.99 -- 593.09 369.70 360.81 octapentacontane -- 217.99 -- 603.40 371.00 361.27 n-octapentacontane -- 217.99 -- 603.40 370.00 361.27 n-nonapentacontane -- 221.99 -- 613.71 371.00 361.72 Hexacontane -- 225.99 -- 624.02 375.00 362.15 n-henhexacontane -- 229.99 -- 634.33 373.00 362.57 dohexacontane -- 233.99 -- 644.63 375.00 362.98 n-trihexacontane -- 237.99 -- 654.94 375.10 363.38 tetrahexacontane -- 241.99 -- 665.25 375.00 363.76 n-pentahexacontane -- 245.99 -- 675.56 376.00 364.13 hexahexacontane -- 249.99 -- 685.87 376.80 364.49 heptahexacontane -- 253.99 -- 696.18 377.30 364.83 n-oclahexacontane -- 257.99 -- 706.49 377.70 365.17 n-nonahexacontane -- 261.99 -- 716.80 378.10 365.50 heptacontane -- 265.99 -- 727.11 380.20 365.82 n-henheptacontane -- 269.99 -- 737.42 373.80 366.13 n-doheptacontane -- 273.99 -- 747.72 374.60 366.43 n-triheptacontane -- 277.99 -- 758.03 375.40 366.73 n-telraheplacontane -- 281.99 -- 768.34 376.20 367.01 n-penlaheplacontane -- 285.99 -- 778.65 377.00 367.29 n-hexaheplacontane -- 289.99 -- 788.96 377.80 367.56 n-heptaheplacontane -- 293.99 -- 799.27 378.60 367.82 n-octaheptacontane -- 297.99 -- 809.58 379.40 368.08 n-nonaheptacontane -- 301.99 -- 819.89 380.20 368.33 n-octacontane -- 305.99 -- 830.20 381.00 368.58 n-henoctacontane -- 309.99 -- 840.51 382.00 368.81 dooctacontane -- 313.99 -- 850.81 383.00 369.05 n-lrioctacontane -- 317.99 -- 861.12 383.80 369.27 n-lelraoctacontane -- 321.99 -- 871.43 384.10 369.50 n-pentaoclacontane -- 325.99 -- 881.74 384.40 369.71 n-hexaoclacontane -- 329.99 -- 892.05 384.70 369.92 n-heptaoctacontane -- 333.99 -- 902.36 385.00 370.13 n-octaoctacontane -- 337.99 -- 912.67 385.30 370.33 n-nonaoctacontane -- 341.99 -- 922.98 385.60 370.53 n-nonacontane -- 345.99 -- 933.29 385.90 370.72 n-hennonacontane -- 349.99 -- 943.60 386.20 370.91 n-dononacontane -- 353.99 -- 953.90 386.50 371.10 n-trinonacontane -- 357.99 -- 964.21 386.80 371.28 tetranonacontane -- 361.99 -- 974.52 387.50 371.45

n-pentanonacontane -- 365.99 -- 984.83 387.50 371.63 n-hexanonacontane -- 369.99 -- 995.14 387.60 371.80 n-heptanonacontane -- 373.99 -- 1005.45 387.70 371.96 n-octanonacontane -- 377.99 -- 1015.76 387.80 372.13 n-nonanonacontane -- 381.99 -- 1026.07 387.90 372.29 Hectane -- 385.99 -- 1036.38 388.00 372.44

SI Table 3. Experimental and calculated values of differential heat capacity of boiling, heat of sublimation, solubility parameter and vapor pressure

3 1/2 Compound ΔCpb(J/K mole) ΔHsub(kJ/mole) δ(J/cm ) VP(log atm) Exp Calc Exp Calc Exp Calc Exp Calc Ethyne -- -36.12 22.70 21.54 -- 15.86 1.68 1.17 Ethene -- -36.12 18.30 17.37 -- 14.13 1.84 1.23 Ethane -- -36.12 -- 19.05 -- 14.76 1.62 1.02 Propadiene -- -33.19 -- 24.10 -- 14.67 0.85 0.68 Propyne -- -51.70 -- 28.65 -- 16.89 0.75 0.48 Propylene -32.60 -51.70 -- 23.17 -- 14.47 1.06 0.68 Cyclopropane -33.74 -45.20 29.20 22.61 -- 15.58 0.85 0.74 Propane -41.58 -47.42 28.50 24.26 -- 14.66 0.97 0.55 2-Methylpropane -35.83 -44.91 -- 27.47 -- 14.51 0.54 0.26 n-Butane -- -56.70 -- 29.92 -- 14.75 0.38 0.15 1,3-Butadiene -34.13 -47.42 -- 28.28 -- 15.46 0.44 0.26 1-Butyne -43.45 -51.70 -- 31.01 -- 16.52 0.27 0.00 1,2-Butadiene -51.43 -51.70 -- 30.45 -- 15.05 0.22 0.09 - 2-Butyne -- -33.19 37.40 36.77 -- 17.89 -0.03 0.26 2-Methylpropene -- -47.42 -- 28.57 -- 14.86 0.48 0.30 1-Butene -38.26 -54.20 -- 27.06 -- 14.57 0.47 0.30 trans-2-Butene -43.75 -47.42 -- 30.13 -- 15.13 0.36 0.20 cis-2-Butene -30.48 -47.42 -- 30.13 -- 15.13 0.36 0.20 Cyclobutane -47.58 -44.62 -- 28.37 -- 15.99 0.19 0.28 - 1,3-Cyclopentadiene -- -54.11 -- 34.44 -- 18.08 -0.24 0.43 3-Methyl-1-butene -- -51.70 -- 28.56 -- 14.24 0.07 0.03 - 1-Pentene -- -59.20 -- 33.04 -- 14.77 -0.08 0.10 - 2-Methyl-1-butene -- -54.20 -- 32.51 -- 14.90 -0.10 0.12 - trans-2-Pentene -- -56.70 -- 34.09 -- 15.13 -0.18 0.21 - cis-2-Pentene -- -56.70 -- 34.09 -- 15.13 -0.18 0.21 - 2-Methyl-2-butene -75.18 -51.70 -- 35.52 15.32 15.36 -0.21 0.25 - Cyclopentane -58.44 -44.17 42.60 34.10 16.70 16.26 -0.38 0.22 2,2-Dimethylpropane -23.38 -33.19 33.20 29.38 -- 14.10 0.23 0.09 - 2-Methylbutane -36.67 -54.20 -- 33.43 13.85 14.70 -0.04 0.20 - n-Pentane -74.11 -61.70 42.00 35.85 14.47 14.89 -0.17 0.25 - 1,4-Pentadiene -- -56.70 -- 34.00 -- 15.27 -0.01 0.15

2-Methyl-1,3- - butadiene -- -51.70 -- 31.81 -- 15.56 -0.14 0.21 - 1-Pentyne -- -56.70 -- 37.02 -- 16.42 -0.24 0.43 3-Methyl-1,2- - butadiene -41.69 -51.70 -- 35.83 15.21 15.28 -0.25 0.35 - 1,trans-3-Pentadiene -- -54.20 -- 35.23 -- 15.87 -0.27 0.28 - cis-1,3-Pentadiene -- -54.20 -- 35.23 -- 15.87 -0.27 0.28 - 1,2-Pentadiene -- -54.20 -- 34.44 -- 15.07 -0.31 0.33 - 2-Pentyne -- -51.70 -- 39.49 -- 17.52 -0.51 0.80 - Methylenecyclobutane -71.57 -53.18 -- 33.47 -- 16.54 -- 0.25 - Cyclopentene -40.10 -54.11 -- 34.43 17.13 17.18 -0.30 0.35 - Spiropentane -67.14 -49.83 -- 32.75 -- 17.19 -0.22 0.10 - 1,5-Hexadiene -- -61.70 -- 36.16 -- 14.78 -0.54 0.35 2,3-Dimethyl-1,3- - butadiene -47.69 -47.42 -- 39.69 15.89 15.74 -0.70 0.66 - trans-1,3-Hexadiene -- -59.20 -- 39.38 -- 15.82 -0.77 0.70 - trans-2,4-Hexadiene -- -52.42 -- 42.03 -- 16.14 -0.94 0.80 - 1-Hexyne -- -61.70 -- 43.21 -- 16.39 -0.75 0.87 - 3-Methylcyclopentene -53.28 -58.40 -- 38.26 -- 16.57 -- 0.70 - 1-Methylcyclopentene -70.22 -58.40 -- 39.18 16.91 16.75 -- 0.73 - Cyclohexene -53.62 -59.15 -- 40.90 17.52 17.47 -0.93 0.92 - 3,3-Dimethyl-1-butene -41.67 -51.70 -- 31.98 13.68 14.12 -0.25 0.30 - 3-Methyl-1-pentene -58.22 -56.70 -- 34.57 14.39 14.46 -0.45 0.39 - 4-Methyl-1-pentene -58.82 -56.70 -- 36.49 14.41 14.70 -0.45 0.46 - 2,3-Dimethyl-1-butene -- -51.70 -- 33.94 14.67 14.55 -0.48 0.41 cis-4-Methyl-2- - pentene -58.82 -54.20 -- 35.56 14.68 14.77 -0.56 0.50 trans-4-methyl-2- - pentene -70.59 -54.20 -- 35.56 14.80 14.77 -0.56 0.50 - 2-Methyl-1-pentene -64.69 -59.20 -- 38.62 15.07 15.06 -0.59 0.55 - 1-Hexene -59.90 -64.20 -- 39.20 15.00 14.96 -0.62 0.53 - 2-Ethyl-1-butene -66.80 -59.20 -- 36.61 15.29 14.98 -0.64 0.53 cis-3-Methyl-2- - pentene -74.54 -56.70 -- 39.60 15.58 15.36 -0.68 0.66 - 2-Methyl-2-pentene -63.83 -56.70 -- 39.60 15.42 15.36 -0.68 0.66

- cis-3-Hexene -61.76 -61.70 -- 38.28 15.23 15.20 -0.66 0.63 - trans-3-Hexene -61.76 -61.70 -- 38.28 15.28 15.20 -0.66 0.63 - trans-2-Hexene -65.00 -61.70 -- 40.30 15.29 15.28 -0.64 0.65 - cis-2-Hexene -60.00 -61.70 -- 40.30 15.39 15.28 -0.64 0.65 trans-3-Methyl-2- - pentene -58.55 -56.70 -- 39.60 15.37 15.36 -0.68 0.66 - 2,3-Dimethyl-2-butene -62.73 -47.42 -- 40.63 15.94 15.45 -0.78 0.68 - Ethylcyclobutane -59.91 -59.97 -- 38.15 15.82 15.55 -- 0.53 - Methylcyclopentane -57.45 -58.40 -- 38.22 16.15 15.90 -0.74 0.62 - Cyclohexane -54.20 -48.08 -- 40.07 16.81 16.54 -0.89 0.77 - 2,2-Dimethylbutane -65.59 -54.20 -- 35.58 13.80 14.39 -0.38 0.44 - 2,3-Dimethylbutane -59.27 -51.70 -- 36.75 14.36 14.61 -0.51 0.56 - 2-Methylpentane -65.25 -59.20 -- 39.49 14.47 14.86 -0.56 0.63 - 3-Methylpentane -62.76 -59.20 -- 39.49 14.69 14.86 -0.60 0.63 - n-Hexane -65.90 -66.70 -- 41.94 14.91 15.04 -0.70 0.67 - Benzene -41.23 -42.79 38.00 39.15 18.53 17.59 -0.90 0.50 - 1,3,5-Hexatriene -- -56.70 -- 47.06 -- 17.79 -0.93 1.42 - 1,4-Cyclohexadiene -33.70 -43.80 -- 39.71 18.34 17.90 -1.06 0.91 - 1,3-Cyclohexadiene -- -43.80 -- 39.71 18.17 17.90 -0.89 0.91 - 1-Heptyne -- -66.70 -- 49.56 -- 16.41 -1.16 1.32 - 1-Ethylcyclopentene -- -60.90 -- 43.46 17.29 16.62 -- 1.19 - 1-Methylcyclohexene -63.50 -59.15 -- 45.48 17.26 17.01 -1.39 1.30 - Methylenecyclohexane -52.81 -59.15 -- 46.19 16.52 17.14 -1.28 1.40 - trans-2-Heptene -- -66.70 -- 46.67 -- 15.44 -1.19 1.10 - cis-3-Methyl-3-hexene -58.51 -61.70 -- 43.92 -- 15.42 -0.97 1.10 4,4-Dimethylpent-1- - ene -- -56.70 -- 38.67 14.12 14.43 -- 0.70 3,3-Dimethylpent-1- - ene -- -56.70 -- 38.09 -- 14.35 -0.86 0.74 trans-4,4- - Dimethylpent-2-ene -- -54.20 -- 39.03 14.60 14.61 -0.84 0.85 2,3,3-Trimethyl-1- - butene -53.10 -51.70 -- 37.36 14.58 14.40 -0.83 0.75 cis-4,4-Dimethylpent- - 2-ene -57.35 -54.20 -- 39.03 14.65 14.61 -0.84 0.85

2,4-Dimethylpent-1- - ene -57.24 -56.70 -- 42.00 14.71 14.96 -0.91 0.92 2,4-Dimethylpent-2- - ene -- -54.20 -- 41.00 15.01 15.00 -- 0.97 2,3-Dimethyl-1- - pentene -- -56.70 -- 40.09 -- 14.74 -0.97 0.86 - (dl)3-Methyl-1-hexene -- -61.70 -- 40.75 -- 14.67 -0.96 0.83 - 3-Ethyl-1-pentene -- -61.70 -- 40.75 -- 14.67 -0.97 0.83 trans-2-Methyl-3- - hexene -- -59.20 -- 39.77 -- 14.87 -1.00 0.93 - (dl)4-Methyl-1-hexene -- -61.70 -- 42.77 -- 14.91 -1.01 0.91 cis-3,4-Dimethylpent- - 2-ene -- -54.20 -- 41.00 -- 15.00 -1.05 0.97 trans-3,4- - Dimethylpent-2-ene -- -54.20 -- 41.00 -- 15.00 -1.05 0.97 - 1-Heptene -70.72 -69.20 -- 45.51 15.41 15.14 -1.11 0.97 3-Methyl-trans-3- - hexene -53.54 -61.70 -- 43.92 15.52 15.42 -0.97 1.10 - 2-Methyl-2-hexene -- -61.70 -- 45.94 -- 15.50 -1.15 1.13 - 3-Ethyl-2-pentene -- -61.70 -- 43.92 -- 15.42 -1.16 1.10 - trans-3-Heptene -- -66.70 -- 44.73 -- 15.38 -1.16 1.09 - cis-3-Heptene -- -66.70 -- 44.73 -- 15.38 -1.16 1.09 2,3-dimethylpent-2- - ene -- -56.70 -- 45.12 -- 15.54 -1.18 1.14 - cis-3-methyl-2-hexene -- -61.70 -- 47.74 -- 16.06 -1.18 1.41 - cis-2-Heptene -- -66.70 -- 46.67 -- 15.44 -1.19 1.10 1,1- - Dimethylcyclopentane -- -54.11 -- 40.15 15.51 15.34 -1.00 0.87 cis-1,3- - Dimethylcyclopentane -59.27 -58.40 -- 41.86 15.54 15.50 -1.06 0.95 (dl)-trans-1,3- - Dimethylcyclopentane -44.53 -54.11 -- 41.51 15.58 15.42 -1.06 0.93 (dl)-trans-1,2- - Dimethylcyclopentane -55.82 -54.11 -- 41.51 15.67 15.42 -1.21 0.93 cis-1,2- - Dimethylcyclopentane -56.38 -58.40 -- 41.86 16.22 15.50 -1.21 0.95 - Ethylcyclopentane -57.45 -60.90 -- 44.50 16.28 15.96 -1.28 1.09 - Methylcyclohexane -49.01 -59.15 -- 44.52 15.96 16.25 -1.22 1.18 - Cycloheptane -53.03 -59.80 -- 47.19 17.25 17.02 -1.55 1.42 - 2,2-Dimethylpentane -61.21 -59.20 -- 41.71 14.22 14.59 -0.86 0.88 - 2,2,3-Trimethylbutane -56.27 -47.42 -- 38.57 14.27 14.26 -0.87 0.77 - 2,4-Dimethylpentane -44.34 -56.70 -- 42.94 14.09 14.80 -0.98 1.01

- 3,3-Dimethylpentane -57.87 -59.20 -- 41.71 14.56 14.59 -0.96 0.88 (dl)2,3- - Dimethylpentane -58.27 -56.70 -- 42.94 14.84 14.80 -1.04 1.01 - 2-Methylhexane -67.08 -64.20 -- 45.71 14.84 15.03 -1.06 1.07 - (dl)3-Methylhexane -64.70 -64.20 -- 45.71 14.97 15.03 -1.09 1.07 - 3-Ethylpentane -61.22 -64.20 -- 45.71 15.12 15.03 -1.12 1.07 - n-Heptane -66.44 -71.70 -- 50.26 15.27 15.18 -1.22 1.10 - Toluene -44.52 -53.87 43.10 46.52 18.02 17.89 -1.43 1.18 - Cycloheptatriene -36.77 -55.51 -- 46.77 18.68 18.95 -1.51 1.65 - Ethylbenzene -60.22 -60.65 -- 51.18 18.02 17.70 -1.90 1.68 - 1,4-Dimethylbenzene -46.96 -49.58 60.80 52.79 17.67 17.86 -1.93 1.79 - 1,3-Dimethylbenzene -46.72 -53.87 -- 53.34 17.75 17.99 -1.96 1.83 - 1,2-Dimethylbenzene -39.80 -53.87 -- 53.34 18.04 17.99 -1.98 1.83 (dl)-4-Vinyl-1- - cyclohexene -58.64 -59.15 -- 51.46 16.88 17.33 -1.68 1.88 - cis-1,5-Cyclooctadiene -46.71 -56.07 -- 52.95 18.26 18.27 -- 2.16 - 1-Octyne -64.26 -71.70 -- 56.05 16.44 16.45 -1.75 1.79 - 4-Octyne -63.36 -66.70 -- 54.96 16.57 17.11 -1.90 2.22 - 3-Octyne -64.73 -66.70 -- 54.96 16.82 17.11 -- 2.22 - 2-Octyne -64.42 -66.70 -- 58.74 17.02 17.23 -2.01 2.24 - Allylcyclopentane -62.10 -63.40 -- 47.78 -- 15.92 -- 1.38 - Vinylcyclohexane -50.74 -59.15 -- 51.42 16.44 16.76 -- 1.79 - Ethylidenecyclohexane -- -59.15 -- 53.40 17.17 17.30 -- 2.02 cis- - Bicyclo[3.3.0]octane -67.46 -56.07 -- 49.84 -- 17.10 -- 1.65 2,4,4-Trimethyl-1- - pentene -62.04 -56.70 -- 44.18 14.55 14.68 -1.23 1.17 trans-2,2-Dimethyl-3- - hexene -77.51 -59.20 -- 43.34 14.72 14.74 -- 1.29 trans-2,5-Dimethyl-3- - hexene -- -52.42 -- 40.75 -- 14.51 -1.24 1.22 2,4,4-Trimethyl-2- - pentene -68.84 -54.20 -- 44.47 14.99 14.83 -1.33 1.33 cis-2,2-Dimethyl-3- - hexene -70.88 -59.20 -- 43.34 14.80 14.74 -- 1.29 2,3,3-Trimethyl-1- - pentene -- -56.70 -- 43.60 -- 14.61 -1.40 1.22 3-Ethyl-2-methyl-1- - pentene -58.39 -61.70 -- 46.40 14.99 14.93 -- 1.32

- 2,5-Dimethyl-2-hexene -- -59.20 -- 49.29 -- 15.36 -1.48 1.51 - 6-Methyl-1-heptene -- -66.70 -- 49.21 -- 15.10 -1.48 1.37 2,3,4-Trimethyl-2- - pentene -- -54.20 -- 46.45 -- 15.18 -1.53 1.46 - 2-Methyl-1-heptene -- -69.20 -- 51.35 -- 15.39 -1.58 1.47 - 2-Ethyl-1-hexene -- -69.20 -- 49.50 -- 15.35 -1.59 1.46 - 1-Octene -66.08 -74.20 -- 51.96 15.55 15.31 -1.64 1.42 - 2,3-Dimethyl-2-hexene -- -61.70 -- 51.59 -- 15.68 -1.62 1.63 - trans-4-Octene -- -71.70 -- 51.34 -- 15.55 -1.63 1.57 - 2-Methyl-2-heptene -- -66.70 -- 52.44 -- 15.64 -1.63 1.60 - cis-4-Octene -- -71.70 -- 51.34 -- 15.55 -1.63 1.57 - trans-2-Octene -- -71.70 -- 53.19 -- 15.59 -1.67 1.57 - cis-2-Octene -- -71.70 -- 53.19 -- 15.59 -1.67 1.57 cis-1,3- - Dimethylcyclohexane -56.84 -59.15 -- 48.17 15.64 15.86 -1.64 1.54 trans-1,3- - Dimethylcyclohexane -58.43 -59.15 -- 48.17 16.03 15.86 -1.64 1.54 cis-1,4- - Dimethylcyclohexane -58.48 -59.15 -- 48.17 15.98 15.86 -1.52 1.54 trans-1,4- - Dimethylcyclohexane -56.98 -54.87 -- 47.67 15.53 15.75 -1.52 1.50 1,1,3- - Trimethylcyclopentane -- -58.40 -- 44.12 -- 15.13 -1.84 1.24 1,2(cis),3(trans)- - trimethylcyclopentane -- -58.40 -- 45.50 -- 15.20 -1.38 1.30 1,cis-2,cis-3- - Trimethylcyclopentane -- -58.40 -- 45.50 -- 15.20 -1.38 1.30 - Isopropylcyclopentane -58.27 -58.40 -- 47.84 16.01 15.76 -1.67 1.48 (dl)-cis-1-Ethyl-2- - methylcyclopentane -- -60.90 -- 48.18 -- 15.61 -1.58 1.45 - Propylcyclopentane -60.57 -65.90 -- 50.97 16.35 16.05 -1.79 1.57 1,trans-2- - Dimethylcyclohexane -55.22 -59.15 -- 48.17 15.76 15.86 -1.59 1.54 1,1- - Dimethylcyclohexane -57.72 -59.15 -- 46.79 15.72 15.80 -1.52 1.47 cis-1,2- - Dimethylcyclohexane -59.77 -59.15 -- 48.17 16.26 15.86 -1.59 1.54 - Ethylcyclohexane -61.37 -61.65 -- 50.89 16.36 16.29 -1.77 1.69 - Cyclooctane -61.13 -51.78 -- 52.30 17.48 16.96 -2.14 1.94 3-Ethyl-2- - methylpentane -62.00 -61.70 -- 49.29 15.07 14.98 -1.50 1.48 - 2,3-Dimethylhexane -62.47 -61.70 -- 49.29 -- 14.98 -1.51 1.48

2,2,4- - Trimethylpentane -59.81 -56.70 -- 45.12 14.09 14.55 -1.19 1.26 2,2,3,3- - Tetramethylbutane -- -36.34 43.37 39.73 -- 13.82 -1.56 0.95 - 2,2-Dimethylhexane -62.98 -64.20 -- 48.00 14.57 14.79 -1.35 1.33 - 2,4-Dimethylhexane -62.88 -61.70 -- 49.29 -- 14.98 -1.40 1.48 - 2,5-Dimethylhexane -63.97 -61.70 -- 49.29 14.67 14.98 -1.40 1.48 2,2,3- - Trimethylpentane -59.29 -56.70 -- 45.12 14.71 14.55 -1.37 1.26 - 3,3-Dimethylhexane -60.73 -64.20 -- 48.00 14.78 14.79 -1.42 1.33 2,3,4- - Trimethylpentane -61.69 -54.20 -- 46.20 14.91 14.71 -1.45 1.39 2,3,3- - Trimethylpentane -57.95 -56.70 -- 45.12 14.88 14.55 -1.45 1.26 - 3,4-Dimethylhexane -62.46 -61.70 -- 49.29 -- 14.98 -1.54 1.48 - 2-Methylheptane -69.61 -69.20 -- 52.08 15.09 15.19 -1.17 1.53 - 4-Methylheptane -69.04 -69.20 -- 52.08 15.17 15.19 -1.57 1.53 3-Ethyl-3- - methylpentane -56.42 -64.20 -- 48.00 14.97 14.79 -1.52 1.33 - 3-Methylheptane -66.88 -69.20 -- 52.08 15.20 15.19 -1.59 1.53 - 3-Ethylhexane -65.10 -69.20 -- 52.08 -- 15.19 -1.58 1.53 - n-Octane -70.71 -76.70 68.10 58.72 15.50 15.33 -1.73 1.54 - Styrene -62.89 -58.15 -- 53.77 18.97 18.64 -2.07 1.93 - Cyclooctatetraene -58.00 -47.50 54.40 51.61 18.99 19.30 -1.99 2.26 - a-Methylstyrene -- -58.15 -- 60.89 -- 18.70 -2.70 2.62 - Indane -59.97 -62.72 -- 62.29 19.44 19.76 -2.71 2.80 - Isopropylbenzene -60.00 -58.15 -- 52.47 17.49 17.10 -2.23 2.01 - Propylbenzene -59.61 -65.65 -- 57.80 17.72 17.62 -2.35 2.19 - 3-Ethyltoluene -56.13 -60.65 -- 58.25 -- 17.86 -2.40 2.36 - 4-Ethyltoluene -59.78 -60.65 -- 58.25 17.78 17.86 -2.42 2.36 - 2-Ethyltoluene -62.94 -60.65 -- 58.25 18.27 17.86 -2.46 2.36 1,3,5- - Trimethylbenzene -60.56 -47.08 -- 59.03 18.00 17.83 -2.56 2.45 1,2,3- - Trimethylbenzene -59.26 -53.87 -- 60.16 18.60 18.06 -2.65 2.50 1,2,4- - Trimethylbenzene -61.34 -58.15 -- 60.89 18.20 18.21 -2.56 2.54 - 1-Nonyne -- -76.70 -- 64.77 -- 16.51 -2.08 2.28

- trans-Hexahydroindan -52.86 -60.84 -- 56.76 -- 17.41 -- 2.30 - 1-Nonene -- -79.20 -- 60.64 -- 15.47 -2.15 1.89 1,1,3- - Trimethylcyclohexane -- -59.15 -- 50.44 -- 15.49 -1.85 1.83 - Propylcyclohexane -68.56 -66.65 -- 57.54 16.37 16.37 -2.26 2.19 - Isopropylcyclohexane -56.82 -59.15 -- 54.17 16.25 16.07 -2.20 2.08 - Butylcyclopentane -73.98 -70.90 -- 57.60 16.43 16.15 -2.28 2.06 2,2,4,4- - Tetramethylpentane -62.27 -56.70 -- 47.30 14.22 14.34 -1.58 1.52 - 2,2,5-Trimethylhexane -66.13 -61.70 -- 51.54 14.42 14.76 -1.66 1.74 - 2,2,4-Trimethylhexane -- -61.70 -- 51.54 -- 14.76 -1.68 1.74 - 2,3,5-Trimethylhexane -65.92 -59.20 -- 52.68 14.81 14.91 -1.81 1.89 - 2,4,4-Trimethylhexane -- -61.70 -- 51.54 -- 14.76 -1.75 1.74 - 2,2-Dimethylheptane -- -69.20 -- 54.44 -- 14.97 -1.85 1.80 2,2,3,4- - Tetramethylpentane -- -54.20 -- 48.34 -- 14.48 -1.78 1.65 2,2-Dimethyl-3- - ethylpentane -- -61.70 -- 51.54 -- 14.76 -1.83 1.74 - 2,2,3-Trimethylhexane -- -61.70 -- 51.54 -- 14.76 -1.82 1.74 2,4-Dimethyl-3- - ethylpentane -- -59.20 -- 52.68 -- 14.91 -1.88 1.89 - 2,3,3-Trimethylhexane -- -61.70 -- 51.54 -- 14.76 -1.89 1.74 - 2,3,4-Trimethylhexane -- -59.20 -- 52.68 -- 14.91 -1.93 1.89 2,2,3,3- - Tetramethylpentane -- -56.70 -- 47.30 -- 14.34 -1.91 1.52 - 3,3,4-Trimethylhexane -- -61.70 -- 51.54 -- 14.76 -1.93 1.74 2,3,3,4- - Tetramethylpentane -- -54.20 -- 48.34 -- 14.48 -1.93 1.65 - 4-Methyloctane -- -74.20 -- 60.69 -- 15.35 -2.05 2.00 - 2-Methyloctane -- -74.20 -- 60.69 -- 15.35 -2.09 2.00 - 3-Methyloctane -- -74.20 -- 60.69 -- 15.35 -2.08 2.00 - 3,3-Diethylpentane -61.17 -69.20 -- 54.44 15.25 14.97 -2.02 1.80 - n-Nonane -75.68 -81.70 71.40 67.30 15.73 15.46 -2.23 2.00 - Indene -61.54 -58.44 -- 61.52 20.27 20.28 -2.84 2.84 1,2,3,4- - Tetrahydronaphthalene -69.27 -63.92 -- 68.78 19.66 19.71 -3.31 3.44 1,3-Dimethyl-4- - ethylbenzene -- -60.65 -- 65.32 -- 17.99 -2.95 3.06

1,2,3,5- - Tetramethylbenzene -54.17 -53.87 -- 66.98 18.13 18.12 -3.18 3.27 - tert-Butylbenzene -64.39 -58.15 -- 55.97 17.10 16.74 -2.54 2.39 - Isobutylbenzene -- -63.15 -- 61.05 16.98 17.28 -2.60 2.59 - (dl)-sec-Butylbenzene -67.61 -63.15 -- 59.12 17.10 17.09 -2.64 2.52 - 3-Isopropyltoluene -- -58.15 -- 59.46 -- 17.28 -2.65 2.69 - 4-Isopropyltoluene -- -58.15 -- 59.46 -- 17.28 -2.67 2.69 - 2-Isopropyltoluene -- -58.15 -- 59.46 -- 17.28 -2.70 2.69 - 1,3-Diethylbenzene -- -65.65 -- 63.01 -- 17.73 -2.83 2.87 - 3-Propyltoluene -- -65.65 -- 65.03 -- 17.80 -2.46 2.89 - 4-Propyltoluene -- -65.65 -- 65.03 -- 17.80 -2.84 2.89 - 1,2-Diethylbenzene -- -65.65 -- 63.01 -- 17.73 -2.86 2.87 - Butylbenzene -79.11 -70.65 -- 64.56 17.70 17.59 -2.86 2.71 1,3-Dimethyl-5- - ethylbenzene -- -60.65 -- 65.32 -- 17.99 -2.87 3.06 - 1,4-Diethylbenzene -- -65.65 -- 63.01 -- 17.73 -2.86 2.87 - 2-Propyltoluene -- -65.65 -- 65.03 -- 17.80 -2.88 2.89 1,4-Dimethyl-2- - ethylbenzene -- -60.65 -- 65.32 -- 17.99 -2.91 3.06 1,2-Dimethyl-4- - ethylbenzene -- -60.65 -- 65.32 -- 17.99 -3.01 3.06 1,3-Dimethyl-2- - ethylbenzene -- -60.65 -- 65.32 -- 17.99 -3.01 3.06 1,2-Dimethyl-3- - ethylbenzene -- -60.65 -- 65.32 -- 17.99 -3.09 3.06 1,2,3,4- - Tetramethylbenzene -41.89 -53.87 -- 66.98 18.38 18.12 -3.32 3.27 1,2,4,5- - Tetramethylbenzene -- -49.58 71.70 66.10 -- 17.96 -3.16 3.36 7-Methyl-3- methylene-1,6- - octadiene(myrcene) -- -66.70 -- 58.86 -- 16.14 -2.58 2.52 - (d)-Limonene -- -59.15 -- 61.61 -- 16.99 -2.72 2.81 5-Isopropyl-2-methyl- - 1,3-cyclohexadiene -- -59.15 -- 58.82 -- 16.75 -2.73 2.68 - (dl)-Limonene -- -59.15 -- 61.61 -- 16.99 -2.72 2.81 - (l)-Limonene -- -59.15 -- 61.61 -- 16.99 -2.72 2.81 - a-Pinene -- -59.80 -- 54.62 -- 16.28 -2.20 2.23 - Decalin -- -52.71 -- 61.47 -- 17.25 -2.79 2.83 trans- - Bicyclo[4.4.0]decane -60.87 -57.00 64.30 62.30 17.12 17.41 -2.79 2.88

cis- - Bicyclo[4.4.0]decane -61.90 -57.00 62.50 62.30 17.60 17.41 -2.79 2.88 - 1-Decene -81.24 -84.20 -- 69.44 15.92 15.62 -2.66 2.38 - tert-Butylcyclohexane -67.96 -59.15 -- 56.38 16.24 15.75 -2.51 2.36 1-Isopropyl-4- - methylcyclohexane -- -59.15 -- 57.82 -- 15.76 -2.45 2.46 - Isobutylcyclohexane -- -64.15 -- 60.94 16.03 16.19 -2.20 2.61 - Butylcyclohexane -69.79 -71.65 -- 64.33 16.34 16.46 -2.76 2.70 2,2,5,5- - Tetramethylhexane -- -57.42 -- 53.17 -- 14.45 -1.94 1.97 2,2,4,5- - Tetramethylhexane -- -59.20 -- 54.89 -- 14.70 -2.10 2.15 - 2,6-Dimethyloctane -- -71.70 -- 62.45 -- 15.33 -2.41 2.46 2,2,3,3- - Tetramethylhexane -- -61.70 -- 53.79 -- 14.57 -2.29 2.01 - 5-Methylnonane -79.90 -79.20 -- 69.42 15.54 15.50 -- 2.49 - 2-Methylnonane -80.35 -79.20 -- 69.42 15.51 15.50 -2.60 2.49 - 3-Methylnonane -80.14 -79.20 -- 69.42 15.57 15.50 -- 2.49 - n-Decane -84.66 -86.70 80.30 75.98 15.84 15.59 -2.73 2.47 - Naphthalene -- -51.42 72.00 64.26 -- 19.47 -3.95 2.91 - 2-Methylnaphthalene -- -59.99 65.70 72.94 -- 19.73 -4.14 3.73 - 1-Methylnaphthalene -52.99 -59.99 -- 72.94 19.88 19.73 -4.05 3.73 - Pentylbenzene -- -75.65 -- 71.46 -- 17.58 -3.24 3.24 - Pentamethylbenzene -- -53.87 71.60 73.80 -- 18.17 -4.34 4.26 - 1-Undecene -- -89.20 -- 78.35 -- 15.77 -3.19 2.87 - n-Pentylcyclohexane -- -76.65 -- 71.26 -- 16.56 -3.31 3.24 - 4-Methyldecane -80.63 -84.20 -- 78.26 15.58 15.64 -- 2.98 - 2-Methyldecane -85.45 -84.20 -- 78.26 15.67 15.64 -3.10 2.98 - n-Undecane -89.12 -91.70 91.50 84.76 15.98 15.72 -3.27 2.95 - Biphenyl -- -56.36 82.00 78.51 -- 19.20 -4.93 4.80 - Acenaphthene -- -58.59 85.00 81.01 -- 20.86 -5.55 4.85 - 2-Ethylnaphthalene -- -62.49 -- 77.52 -- 19.39 -4.38 4.27 1,8- - Dimethylnaphthalene -- -55.71 82.70 78.80 -- 19.47 -5.18 4.80 2,6- - Dimethylnaphthalene -- -55.71 84.10 78.80 -- 19.47 -5.13 4.80

1,3- - Dimethylnaphthalene -- -59.99 -- 79.96 -- 19.66 -4.52 4.74 2,3- - Dimethylnaphthalene -- -55.71 82.00 78.80 -- 19.47 -- 4.80 - 1-Ethylnaphthalene -- -62.49 -- 77.52 -- 19.39 -4.16 4.27 2,7- - Dimethylnaphthalene -- -55.71 84.60 78.80 -- 19.47 -5.13 4.80 1,7- - Dimethylnaphthalene -- -55.71 -- 78.80 -- 19.47 -4.72 4.80 1,6- - Dimethylnaphthalene -- -59.99 -- 79.96 -- 19.66 -4.72 4.74 1,4- - Dimethylnaphthalene -- -55.71 -- 78.80 -- 19.47 -4.55 4.80 1,5- - Dimethylnaphthalene -- -55.71 -- 78.80 -- 19.47 -5.18 4.80 - Cyclohexylbenzene -59.46 -65.61 -- 76.49 18.46 18.66 -4.28 4.11 1,3- - Diisopropylbenzene -- -60.65 -- 65.41 -- 16.79 -3.29 3.55 1,4- - Diisopropylbenzene -- -52.08 -- 63.50 -- 16.49 -3.49 3.42 - Hexylbenzene -- -80.65 -- 78.49 -- 17.60 -3.80 3.78 - Hexamethylbenzene -- -42.79 81.00 75.74 -- 17.46 -5.95 5.16 - Bicyclohexyl -63.21 -62.04 -- 72.02 16.98 17.06 -3.85 3.81 - 1-Dodecene -94.33 -94.20 -- 87.36 16.20 15.90 -3.68 3.38 - n-Hexylcyclohexane -80.93 -81.65 -- 80.41 16.46 16.66 -3.82 3.78 2,2,4,6,6- - Pentamethylheptane -63.90 -64.20 -- 63.89 -- 14.74 -- 2.96 - n-Dodecane -94.67 -96.70 100.20 93.62 16.11 15.83 -3.75 3.43 - Fluorene -- -56.36 83.00 85.82 -- 20.06 -6.10 5.84 - Diphenylmethane -75.78 -63.15 87.20 81.26 -- 19.26 -4.97 4.59 2- - Isopropylnaphthalene -- -59.99 -- 78.54 -- 18.75 -5.17 4.62 - Heptylbenzene -- -85.65 -- 87.72 -- 17.62 -4.39 4.34 - 1-Tridecene -- -99.20 -- 96.45 -- 16.03 -4.08 3.90 - n-Heptylcyclohexane -85.96 -86.65 -- 89.66 16.50 16.76 -4.28 4.33 - n-Tridecane -98.34 -101.70 91.40 102.56 16.18 15.95 -4.13 3.93 - Anthracene -- -52.63 99.00 89.31 -- 20.46 -- 6.47 - Phenanthrene -- -56.92 91.00 90.71 -- 20.68 -6.80 6.43 - 1-Methylfluorene -- -60.65 -- 94.10 -- 20.16 -6.40 6.83 - 1,1-Diphenylethane -- -60.65 -- 73.86 -- 17.18 -4.65 3.86

1,2,3,4,5,6,7,8- - Octahydroanthracene -- -66.80 82.00 77.05 -- 18.97 -- 3.92 - Octylbenzene -- -90.65 -- 97.05 -- 17.66 -4.83 4.91 - 1-Tetradecene -- -104.20 -- 105.62 -- 16.15 -4.70 4.43 - Cyclohexane,octyl- -- -91.65 -- 99.02 -- 16.85 -4.92 4.90 - n-Tetradecane -103.68 -106.70 117.60 111.56 16.27 16.05 -4.82 4.44 - 1-Methylphenanthrene -- -61.20 -- 99.19 -- 20.74 -7.70 7.44 - 9-Methylanthracene -- -61.20 98.95 99.19 -- 20.74 -7.28 7.44 - 2-Methylanthracene -- -56.92 -- 97.60 -- 20.52 -8.15 7.46 - Benzene,nonyl- -- -95.65 -- 106.47 -- 17.70 -5.12 5.48 - 1-Pentadecene -- -109.20 -- 114.85 -- 16.26 -5.22 4.96 - n-Nonylcyclohexane -- -96.65 -- 108.47 -- 16.95 -5.49 5.48 - n-Pentadecane -108.55 -111.70 107.80 120.62 16.32 16.15 -5.35 4.95 - Pyrene -- -48.83 99.00 91.69 -- 21.23 -8.23 6.93 - Fluoranthene -- -57.40 100.00 96.59 -- 21.41 -7.92 7.22 1,2,3,6,7,8- - Hexahydropyrene -- -63.16 84.80 89.72 -- 20.11 -- 5.87 - 1-Hexadecene -114.73 -109.20 -- 119.27 16.45 16.28 -5.46 5.51 - n-Decylcyclohexane -108.09 -101.65 -- 118.00 16.68 17.04 -5.87 6.06 - n-Hexadecane -115.24 -116.70 135.60 129.72 16.41 16.24 -5.73 5.46 - 2,3-Benzofluorene -- -61.68 -- 113.39 -- 21.10 -10.14 9.60 - Benzo(a)fluorene -- -61.68 -- 113.39 -- 21.10 -9.50 9.60 - n-Undecylbenzene -- -105.65 -- 125.55 -- 17.79 -6.50 6.66 - 1-Heptadecene -- -119.20 -- 133.48 -- 16.47 -6.22 6.05 - n-Heptadecane -119.60 -121.70 125.10 138.85 16.44 16.32 -6.52 6.01 - 10.2 Chrysene -- -57.82 123.00 116.49 -- 21.34 -11.09 4 - 10.2 Benz(a)anthracene -- -62.11 119.50 118.51 -- 21.58 -9.56 6 - 10.2 Triphenylene -- -51.03 120.10 113.34 -- 20.96 -10.56 1 - 10.2 Naphthacene -- -53.54 128.00 114.50 -- 21.10 -- 2

- 10.2 Benzo(c)phenanthrene -- -57.82 106.30 116.49 -- 21.34 -- 4 - 10.4 p-Terphenyl -- -64.61 118.00 120.44 -- 20.16 -9.88 3 - Dodecylbenzene -- -110.65 -- 135.18 -- 17.84 -7.17 7.26 - 1-Octadecene -- -124.20 -- 142.85 -- 16.56 -7.05 6.60 - n-Dodecylcyclohexane -121.91 -111.65 -- 137.24 16.74 17.21 -- 7.25 - n-Octadecane -127.50 -126.70 152.70 148.01 -- 16.40 -6.35 6.69 - Tridecylbenzene -- -115.65 -- 144.86 -- 17.89 -7.78 7.87 - 1-Nonadecene -- -129.20 -- 152.24 -- 16.64 -7.30 7.16 - Tridecylcyclohexane -- -116.65 -- 146.94 -- 17.29 -7.92 7.90 - n-Nonadecane -133.09 -131.70 143.60 157.18 -- 16.47 -7.19 7.38 - 10.7 Perylene -- -53.92 135.90 118.51 -- 21.91 -11.16 0 - 11.0 Benzo(k)fluoranthene -- -58.20 133.80 122.41 -- 21.92 -- 7 - 10.7 Benzo(a)pyrene -- -62.49 122.50 122.92 -- 22.42 -11.14 9 - 10.7 Benzo(e)pyrene -- -58.20 117.90 120.70 -- 22.16 -11.12 4 - Eicosane -138.71 -136.70 170.40 166.37 -- 16.53 -8.22 8.07 - pentadecylbenzene -- -125.65 -- 164.35 -- 17.97 -8.02 9.14 - Heneicosane -- -141.70 142.00 175.55 -- 16.59 -- 8.76 - 11.2 Benzo(ghi)perylene -- -54.26 129.90 122.53 -- 22.69 -- 0 - 11.2 Anthanthrene -- -54.26 135.00 122.53 -- 22.69 -- 0 - 14.1 Dibenz(a,h)anthracene -- -58.55 142.00 142.37 -- 21.80 -- 7 - 14.0 Pentacene -- -54.26 157.00 139.79 -- 21.54 -- 9 - 14.4 Dibenz(a,c)anthracene -- -62.83 145.90 144.98 -- 22.06 -- 0 - 14.8 Dibenzo(a,e)pyrene -- -63.14 146.40 149.42 -- 22.76 -- 3

- 18.0 Dibenzo(g,p)chrysene -- -54.86 150.90 165.16 -- 21.87 -- 5

SI Table 4. Experimental and calculated values of molar volume, aqueous activity coefficient, octanol solubility and aqueous solubility

logγw(log logSo(log logSw(log Compound V(cm3/mole) mole/L) mole/L) mole/L) Exp Calc Exp Calc Exp Calc Exp Calc Propyne -- 64.48 1.04 1.04 -- 0.30 -1.04 -1.04 Propylene -- 75.79 2.32 1.62 -- 0.63 -2.32 -1.62 Cyclopropane -- 66.69 2.04 1.56 -- 0.50 -2.04 -1.56 Propane -- 81.50 2.85 2.59 -- 0.56 -2.85 -2.59 2-Methylpropane -- 96.92 3.08 2.77 -- 0.49 -3.08 -2.77 n-Butane -- 97.77 2.98 3.22 0.69 0.45 -2.98 -3.22 1,3-Butadiene -- 84.81 1.87 1.83 -- 0.41 -1.87 -1.83 1-Butyne -- 82.40 1.28 1.14 -- 0.28 -1.28 -1.14 2-Butyne 78.28 78.22 -- 2.08 -- 0.14 -- -2.08 2-Methylpropene -- 89.93 2.33 2.01 -- 0.47 -2.33 -2.01 1-Butene -- 92.65 2.40 2.20 -- 0.50 -2.40 -2.20 trans-2-Butene -- 90.69 2.04 1.99 -- 0.43 -2.04 -1.99 cis-2-Butene -- 90.69 1.93 1.99 -- 0.43 -1.93 -1.99 1,3-Cyclopentadiene 82.94 81.87 1.56 1.60 -- 0.12 -1.56 -1.60 3-Methyl-1-butene -- 109.58 2.73 2.49 -- 0.47 -2.73 -2.49 1-Pentene 109.42 108.92 2.68 2.87 -- 0.40 -2.68 -2.87 2-Methyl-1-butene 107.91 106.80 2.73 2.59 -- 0.39 -2.73 -2.59 trans-2-Pentene 108.24 107.56 2.54 2.57 -- 0.36 -2.54 -2.57 cis-2-Pentene 106.92 107.56 2.54 2.57 -- 0.36 -2.54 -2.57 2-Methyl-2-butene 105.95 104.84 2.56 2.37 -- 0.34 -2.56 -2.37 Cyclopentane 94.15 94.60 2.65 2.60 -- 0.27 -2.65 -2.60 2,2-Dimethylpropane -- 111.98 3.34 3.17 -- 0.48 -3.34 -3.17 2-Methylbutane 116.43 113.19 3.18 3.44 -- 0.40 -3.18 -3.44 n-Pentane 115.26 114.05 3.28 3.82 -- 0.37 -3.28 -3.82 1,4-Pentadiene 103.06 103.06 2.09 2.31 -- 0.36 -2.09 -2.31 2-Methyl-1,3-butadiene 100.80 100.80 2.03 2.03 -- 0.33 -2.03 -2.03 1-Pentyne 98.72 98.67 1.64 1.81 -- 0.24 -1.64 -1.81 3-Methyl-1,2-butadiene 109.87 109.87 -- 2.01 -- 0.34 -- -2.01 1,trans-3-Pentadiene 101.52 99.72 -- 2.20 -- 0.30 -- -2.20 cis-1,3-Pentadiene 99.30 99.72 -- 2.20 -- 0.30 -- -2.20 2-Pentyne 95.81 96.15 -- 2.19 -- 0.15 -- -2.19 Cyclopentene 88.24 88.24 2.10 2.10 -- 0.19 -2.10 -2.10 1,5-Hexadiene 118.71 120.07 2.69 2.49 -- 0.36 -2.69 -2.49 2,3-Dimethyl-1,3-butadiene 113.00 114.30 2.40 2.59 -- 0.28 -2.40 -2.59 trans-1,3-Hexadiene 115.06 116.58 -- 2.78 -- 0.26 -- -2.78

trans-2,4-Hexadiene 115.70 114.63 -- 2.57 -- 0.23 -- -2.57 1-Hexyne 114.73 114.95 2.36 2.45 -- 0.21 -2.36 -2.45 1-Methylcyclopentene 105.32 105.03 -- 2.63 -- 0.20 -- -2.63 Cyclohexene 101.29 102.20 2.59 2.62 -- 0.14 -2.59 -2.62 3,3-Dimethyl-1-butene 128.88 126.29 -- 2.90 -- 0.42 -- -2.90 3-Methyl-1-pentene 126.18 125.85 -- 3.15 -- 0.38 -- -3.15 4-Methyl-1-pentene 126.75 124.33 3.24 3.06 -- 0.36 -3.24 -3.06 2,3-Dimethyl-1-butene 124.13 123.72 -- 2.87 -- 0.38 -- -2.87 cis-4-Methyl-2-pentene 125.42 124.48 -- 2.85 -- 0.35 -- -2.85 trans-4-methyl-2-pentene 125.61 124.48 -- 2.85 -- 0.35 -- -2.85 2-Methyl-1-pentene 123.40 123.07 3.03 3.26 -- 0.32 -3.03 -3.26 1-Hexene 125.05 125.19 3.23 3.51 -- 0.33 -3.23 -3.51 2-Ethyl-1-butene 121.97 123.66 -- 3.17 -- 0.33 -- -3.17 cis-3-Methyl-2-pentene 121.97 121.70 -- 2.95 -- 0.30 -- -2.95 2-Methyl-2-pentene 122.50 121.70 -- 2.95 -- 0.30 -- -2.95 cis-3-Hexene 124.31 124.42 -- 3.15 -- 0.31 -- -3.15 trans-3-Hexene 124.31 124.42 -- 3.15 -- 0.31 -- -3.15 trans-2-Hexene 124.13 123.83 3.23 3.24 -- 0.30 -3.23 -3.24 cis-2-Hexene 122.50 123.83 3.23 3.24 -- 0.30 -3.23 -3.24 trans-3-Methyl-2-pentene 121.97 121.70 -- 2.95 -- 0.30 -- -2.95 2,3-Dimethyl-2-butene 118.87 118.99 -- 2.76 -- 0.29 -- -2.76 Ethylcyclobutane 115.60 114.91 -- 3.44 -- 0.29 -- -3.44 Methylcyclopentane 112.36 112.60 3.30 3.29 -- 0.26 -3.30 -3.29 Cyclohexane 108.04 108.56 3.18 3.12 0.67 0.21 -3.18 -3.12 2,2-Dimethylbutane 133.74 128.25 3.67 3.84 -- 0.38 -3.67 -3.84 2,3-Dimethylbutane 130.25 128.60 3.58 3.63 -- 0.36 -3.58 -3.63 2-Methylpentane 131.98 129.46 3.79 4.08 -- 0.33 -3.79 -4.08 3-Methylpentane 129.79 129.46 3.68 4.08 -- 0.33 -3.68 -4.08 n-Hexane 131.61 130.32 3.96 4.38 0.58 0.31 -3.96 -4.38 Benzene 88.90 91.65 1.64 1.87 0.75 0.15 -1.64 -1.87 1,4-Cyclohexadiene 94.60 95.83 2.06 2.12 -- 0.12 -2.06 -2.12 1,3-Cyclohexadiene 93.00 95.83 -- 2.12 -- 0.12 -- -2.12 1,6Heptadiene 134.69 136.34 3.34 3.16 -- 0.30 -3.34 -3.16 1-Heptyne 131.20 131.22 3.01 3.04 -- 0.18 -3.01 -3.04 4-Methylcyclohex-1-ene 120.36 120.19 -- 3.31 -- 0.16 -- -3.31 3-Ethylcyclopentene 122.82 122.51 -- 3.46 -- 0.18 -- -3.46 (dl)-1,5-Dimethylcyclopentene 123.29 123.02 -- 3.32 -- 0.21 -- -3.32 1,2-Dimethylcyclopentene 120.51 121.82 -- 3.16 -- 0.21 -- -3.16 1-Ethylcyclopentene 120.51 121.89 -- 3.21 -- 0.18 -- -3.21 1-Methylcyclohexene 118.58 118.99 3.27 3.15 -- 0.15 -3.27 -3.15

100

Cycloheptene 116.71 116.16 3.16 3.14 -- 0.12 -3.16 -3.14 Methylenecyclohexane 123.14 119.82 -- 3.31 -- 0.14 -- -3.31 trans-2-Heptene 140.07 140.10 3.83 3.87 -- 0.25 -3.83 -3.87 4,4-Dimethylpent-1-ene 143.97 139.40 -- 3.46 -- 0.35 -- -3.46 3,3-Dimethylpent-1-ene 140.88 142.56 -- 3.56 -- 0.35 -- -3.56 trans-4,4-Dimethylpent-2-ene 142.30 141.20 -- 3.26 -- 0.33 -- -3.26 2,3,3-Trimethyl-1-butene 139.28 140.44 -- 3.28 -- 0.35 -- -3.28 cis-4,4-Dimethylpent-2-ene 140.27 141.20 -- 3.26 -- 0.33 -- -3.26 2,4-Dimethylpent-1-ene 141.48 138.48 -- 3.44 -- 0.30 -- -3.44 2,4-Dimethylpent-2-ene 141.28 138.63 -- 3.24 -- 0.29 -- -3.24 2,3-Dimethyl-1-pentene 139.28 139.99 -- 3.54 -- 0.32 -- -3.54 3-Ethyl-1-pentene 141.08 142.12 -- 3.79 -- 0.32 -- -3.79 5-Methyl-1-hexene 141.89 140.60 -- 3.73 -- 0.30 -- -3.73 (dl)4-Methyl-1-hexene 140.47 140.60 -- 3.73 -- 0.30 -- -3.73 cis-3,4-Dimethylpent-2-ene 138.30 138.63 -- 3.24 -- 0.29 -- -3.24 trans-3,4-Dimethylpent-2-ene 138.30 138.63 -- 3.24 -- 0.29 -- -3.24 2-Methyl-1-hexene 139.67 139.34 -- 3.89 -- 0.27 -- -3.89 1-Heptene 140.88 141.46 3.73 4.10 -- 0.28 -3.73 -4.10 3-Methyl-trans-3-hexene 138.30 138.57 -- 3.54 -- 0.25 -- -3.54 2-Methyl-2-hexene 138.69 137.97 -- 3.62 -- 0.25 -- -3.62 3-Ethyl-2-pentene 136.38 138.57 -- 3.54 -- 0.25 -- -3.54 trans-3-Heptene 140.67 140.69 -- 3.82 -- 0.25 -- -3.82 cis-3-Heptene 139.67 140.69 -- 3.82 -- 0.25 -- -3.82 2,3-dimethylpent-2-ene 134.88 135.85 -- 3.34 -- 0.25 -- -3.34 cis-3-methyl-2-hexene 137.71 137.81 -- 3.87 -- 0.20 -- -3.87 cis-2-Heptene 138.88 140.10 3.83 3.87 -- 0.25 -3.83 -3.87 1,1-Dimethylcyclopentane 130.23 129.80 -- 3.71 -- 0.28 -- -3.71 cis-1,3-Dimethylcyclopentane 131.80 130.60 -- 3.98 -- 0.26 -- -3.98 (dl)-trans-1,3- Dimethylcyclopentane 131.09 130.60 -- 3.98 -- 0.27 -- -3.98 (dl)-trans-1,2- Dimethylcyclopentane 130.75 130.60 -- 3.98 -- 0.27 -- -3.98 cis-1,2-Dimethylcyclopentane 127.02 130.60 -- 3.98 -- 0.26 -- -3.98 Ethylcyclopentane 128.19 128.87 -- 3.96 -- 0.22 -- -3.96 Methylcyclohexane 127.69 126.56 3.85 3.81 -- 0.20 -3.85 -3.81 Cycloheptane 121.07 122.52 3.51 3.64 -- 0.15 -3.51 -3.64 2,2-Dimethylpentane 148.68 144.52 4.36 4.47 -- 0.32 -4.36 -4.47 2,2,3-Trimethylbutane 145.23 143.66 -- 4.03 -- 0.36 -- -4.03 2,4-Dimethylpentane 148.90 144.87 4.26 4.30 -- 0.30 -4.26 -4.30 3,3-Dimethylpentane 144.60 144.52 4.23 4.47 -- 0.32 -4.23 -4.47 (dl)2,3-Dimethylpentane 144.19 144.87 4.28 4.30 -- 0.30 -4.28 -4.30

101

2-Methylhexane 147.58 145.73 4.60 4.67 -- 0.28 -4.60 -4.67 (dl)3-Methylhexane 145.87 145.73 4.31 4.67 -- 0.28 -4.31 -4.67 3-Ethylpentane 143.57 145.73 -- 4.67 -- 0.28 -- -4.67 n-Heptane 146.51 146.59 4.47 4.90 -- 0.26 -4.47 -4.90 Toluene 106.27 106.57 2.24 2.38 0.67 0.11 -2.24 -2.38 Cycloheptatriene 103.76 103.42 2.17 2.13 -- 0.05 -2.17 -2.13 Ethylbenzene 122.46 123.44 2.80 2.96 -- 0.10 -2.80 -2.96 1,4-Dimethylbenzene 123.31 121.49 2.82 2.89 0.61 0.09 -2.82 -2.89 1,3-Dimethylbenzene 122.26 121.49 2.82 2.89 -- 0.09 -2.82 -2.89 1,2-Dimethylbenzene 118.36 121.49 2.78 2.89 -- 0.09 -2.78 -2.89 (dl)-4-Vinyl-1-cyclohexene 130.35 130.58 3.34 3.26 -- 0.12 -3.34 -3.26 cis-1,5-Cyclooctadiene 122.65 123.75 -- 3.16 -- 0.07 -- -3.16 1-Octyne 147.52 147.49 3.66 3.60 -- 0.16 -3.66 -3.60 4-Octyne 146.74 146.61 -- 3.59 -- 0.12 -- -3.59 3-Octyne 146.54 146.61 -- 3.59 -- 0.12 -- -3.59 2-Octyne 145.19 144.96 -- 4.09 -- 0.11 -- -4.09 Vinylcyclohexane 137.75 136.95 -- 3.77 -- 0.15 -- -3.77 Ethylidenecyclohexane 134.06 134.73 -- 3.68 -- 0.12 -- -3.68 Cyclooctene 130.26 130.11 -- 3.66 -- 0.09 -- -3.66 2,4,4-Trimethyl-1-pentene 156.95 153.54 -- 3.84 -- 0.29 -- -3.84 trans-2,2-Dimethyl-3-hexene 160.31 158.06 -- 3.84 -- 0.28 -- -3.84 trans-2,5-Dimethyl-3-hexene 158.06 158.27 -- 3.72 -- 0.30 -- -3.72 2,4,4-Trimethyl-2-pentene 155.43 155.34 -- 3.65 -- 0.28 -- -3.65 cis-2,2-Dimethyl-3-hexene 158.06 158.06 -- 3.84 -- 0.28 -- -3.84 3-Ethyl-2-methyl-1-pentene 155.86 156.26 -- 4.17 -- 0.27 -- -4.17 2,3,4-Trimethyl-2-pentene 151.04 152.78 -- 3.62 -- 0.25 -- -3.62 2-Methyl-1-heptene 155.64 155.61 -- 4.49 -- 0.23 -- -4.49 1-Octene 156.95 157.73 4.44 4.66 -- 0.23 -4.44 -4.66 2,3-Dimethyl-2-hexene 151.44 152.12 -- 4.01 -- 0.21 -- -4.01 trans-4-Octene 157.17 156.96 -- 4.45 -- 0.21 -- -4.45 2-Methyl-2-heptene 155.86 154.25 -- 4.26 -- 0.21 -- -4.26 cis-3-Octene 157.83 156.96 -- 4.45 -- 0.21 -- -4.45 cis-4-Octene 155.64 156.96 -- 4.45 -- 0.21 -- -4.45 trans-2-Octene 156.30 156.37 -- 4.47 -- 0.21 -- -4.47 tran-3-Octene 156.95 156.96 -- 4.45 -- 0.21 -- -4.45 cis-2-Octene 155.86 156.37 -- 4.47 -- 0.21 -- -4.47 cis-1,3-Dimethylcyclohexane 146.50 144.56 -- 4.50 -- 0.21 -- -4.50 trans-1,3-Dimethylcyclohexane 142.94 144.56 -- 4.50 -- 0.21 -- -4.50 cis-1,4-Dimethylcyclohexane 143.32 144.56 4.47 4.50 -- 0.21 -4.47 -4.50 trans-1,4-Dimethylcyclohexane 147.06 144.56 4.47 4.50 -- 0.22 -4.47 -4.50

102

1,1,3-Trimethylcyclopentane 150.03 147.80 4.48 4.40 -- 0.26 -4.48 -4.40 1,1,2-Trimethylcyclopentane 145.17 147.80 -- 4.40 -- 0.26 -- -4.40 1,cis-2,trans-4- Trimethylcyclopentane 147.08 148.60 -- 4.68 -- 0.26 -- -4.68 Isopropylcyclopentane 144.43 144.28 -- 4.15 -- 0.22 -- -4.15 Propylcyclopentane 144.61 145.14 4.74 4.59 -- 0.19 -4.74 -4.59 1,trans-2-Dimethylcyclohexane 144.61 144.56 4.33 4.50 -- 0.21 -4.33 -4.50 1,1-Dimethylcyclohexane 143.69 143.76 -- 4.23 -- 0.21 -- -4.23 cis-1,2-Dimethylcyclohexane 140.97 144.56 4.27 4.50 -- 0.21 -4.27 -4.50 Ethylcyclohexane 142.41 142.83 4.25 4.48 -- 0.18 -4.25 -4.48 Cyclooctane 134.23 136.48 4.15 4.16 -- 0.14 -4.15 -4.16 3-Ethyl-2-methylpentane 158.87 161.14 -- 4.93 -- 0.25 -- -4.93 2,2,4-Trimethylpentane 165.07 159.93 4.67 4.70 -- 0.29 -4.67 -4.70 2,2-Dimethylhexane 164.36 160.79 5.76 5.07 -- 0.27 -5.76 -5.07 2,5-Dimethylhexane 164.60 161.14 -- 4.93 -- 0.25 -- -4.93 2,2,3-Trimethylpentane 159.54 159.93 4.68 4.70 -- 0.29 -4.68 -4.70 3,3-Dimethylhexane 160.89 160.79 -- 5.07 -- 0.27 -- -5.07 2,3,4-Trimethylpentane 158.87 160.28 4.70 4.49 -- 0.28 -4.70 -4.49 2,3,3-Trimethylpentane 157.34 159.93 -- 4.70 -- 0.29 -- -4.70 2-Methylheptane 163.65 162.00 -- 5.23 -- 0.24 -- -5.23 4-Methylheptane 162.03 162.00 -- 5.23 -- 0.24 -- -5.23 3-Ethyl-3-methylpentane 158.65 160.79 -- 5.07 -- 0.27 -- -5.07 3-Methylheptane 161.80 162.00 5.16 5.23 -- 0.24 -5.16 -5.23 n-Octane 162.49 162.86 5.24 5.39 0.49 0.22 -5.24 -5.39 Styrene 115.15 116.20 2.53 2.59 -- 0.06 -2.53 -2.59 Cyclooctatetraene 112.59 111.02 -- 2.15 -- 0.03 -- -2.15 a-Methylstyrene 130.41 130.94 3.01 2.97 -- 0.05 -3.01 -2.97 trans-Methylstyrene 130.30 131.10 -- 2.96 -- 0.05 -- -2.96 Indane 122.61 122.61 3.04 3.03 -- 0.02 -3.04 -3.03 Isopropylbenzene 139.44 140.36 3.29 3.25 -- 0.13 -3.29 -3.25 Propylbenzene 139.44 139.71 3.36 3.63 -- 0.09 -3.36 -3.63 4-Ethyltoluene 139.61 138.36 3.10 3.48 -- 0.08 -3.10 -3.48 2-Ethyltoluene 135.51 138.36 3.21 3.48 -- 0.08 -3.21 -3.48 1,3,5-Trimethylbenzene 138.96 136.42 3.40 3.41 -- 0.09 -3.40 -3.43 1,2,3-Trimethylbenzene 134.45 136.42 3.20 3.41 -- 0.07 -3.20 -3.41 1,2,4-Trimethylbenzene 137.21 136.42 3.32 3.41 -- 0.07 -3.32 -3.41 1-Nonyne 163.89 163.76 4.24 4.13 -- 0.14 -4.24 -4.13 1-Nonene 173.17 174.00 5.05 5.19 -- 0.20 -5.05 -5.19 1,1,3-Trimethylcyclohexane -- 161.76 4.85 4.92 -- 0.21 -4.85 -4.92 Propylcyclohexane 158.99 159.10 -- 5.11 -- 0.15 -- -5.11 Isopropylcyclohexane 157.41 158.24 -- 4.67 -- 0.18 -- -4.67

103

Butylcyclopentane 160.82 161.41 -- 5.19 -- 0.17 -- -5.19 2,2,4,4-Tetramethylpentane 178.39 175.00 -- 5.09 -- 0.29 -- -5.09 2,2,5-Trimethylhexane 181.41 176.20 5.05 5.33 -- 0.25 -5.05 -5.33 2,2,4-Trimethylhexane 179.13 176.20 -- 5.33 -- 0.25 -- -5.33 2,3,5-Trimethylhexane 177.65 176.55 -- 5.16 -- 0.24 -- -5.16 2,4,4-Trimethylhexane 177.15 176.20 -- 5.33 -- 0.25 -- -5.33 2,2-Dimethylheptane 178.14 177.06 -- 5.63 -- 0.23 -- -5.63 2,2,3,4-Tetramethylpentane 173.56 175.35 -- 4.89 -- 0.27 -- -4.89 2,4-Dimethylheptane 179.38 177.41 -- 5.53 -- 0.22 -- -5.53 2,2-Dimethyl-3-ethylpentane 175.70 176.20 -- 5.33 -- 0.25 -- -5.33 2,2,3-Trimethylhexane 175.70 176.20 -- 5.33 -- 0.25 -- -5.33 4,4-Dimethylheptane 176.67 177.06 -- 5.63 -- 0.23 -- -5.63 2,6-Dimethylheptane 180.90 177.41 -- 5.53 -- 0.22 -- -5.53 3,5-Dimethylheptane 177.40 177.41 -- 5.53 -- 0.22 -- -5.53 2,5-Dimethylheptane 178.88 177.41 -- 5.53 -- 0.22 -- -5.53 2,4-Dimethyl-3-ethylpentane 173.79 176.55 -- 5.16 -- 0.24 -- -5.16 2,3,3-Trimethylhexane 173.79 176.20 -- 5.33 -- 0.25 -- -5.33 2,3,4-Trimethylhexane 173.56 176.55 -- 5.16 -- 0.24 -- -5.16 2,2,3,3-Tetramethylpentane 169.43 175.00 -- 5.09 -- 0.29 -- -5.09 3-Methyl-4-ethylhexane 173.32 177.41 -- 5.53 -- 0.22 -- -5.53 3,3,4-Trimethylhexane 172.16 176.20 -- 5.33 -- 0.25 -- -5.33 2,3-Dimethylheptane 176.67 177.41 -- 5.53 -- 0.22 -- -5.53 3,4-Dimethylheptane 175.46 177.41 -- 5.53 -- 0.22 -- -5.53 4-Ethylheptane 176.18 178.27 -- 5.76 -- 0.20 -- -5.76 2,3,3,4-Tetramethylpentane 169.88 175.35 -- 4.89 -- 0.27 -- -4.89 4-Methyloctane 178.14 178.27 6.05 5.76 -- 0.20 -6.05 -5.76 3-Ethylheptane 176.42 178.27 -- 5.76 -- 0.20 -- -5.76 2-Methyloctane 179.89 178.27 -- 5.76 -- 0.20 -- -5.76 3-Methyloctane 177.89 178.27 -- 5.76 -- 0.20 -- -5.76 3,3-Diethylpentane 170.11 177.06 -- 5.63 -- 0.23 -- -5.63 n-Nonane 177.72 179.13 5.77 5.84 -- 0.19 -5.77 -5.84 Indene 117.10 116.25 -- 2.53 -- 0.01 -- -2.53 1,2,3,4-Tetrahydronaphthalene 135.88 136.57 3.45 3.55 -- 0.02 -3.45 -3.55 1,2,3,5-Tetramethylbenzene 150.64 151.34 -- 3.92 -- 0.06 -- -4.00 tert-Butylbenzene 154.81 157.08 3.66 3.66 -- 0.13 -3.66 -3.66 Isobutylbenzene 157.35 155.12 4.12 3.82 -- 0.10 -4.12 -3.82 (dl)-sec-Butylbenzene 155.71 156.63 3.88 3.92 -- 0.11 -3.88 -3.92 3-Isopropyltoluene -- 155.28 3.50 3.76 -- 0.10 -3.50 -3.76 4-Isopropyltoluene 156.07 155.28 3.76 3.76 -- 0.10 -3.76 -3.76 2-Isopropyltoluene 154.28 155.28 3.76 3.76 -- 0.10 -3.76 -3.76

104

1,3-Diethylbenzene 155.35 155.22 3.75 4.06 -- 0.08 -3.75 -4.06 3-Propyltoluene 155.89 154.63 -- 4.14 -- 0.08 -- -4.14 4-Propyltoluene 156.43 154.63 -- 4.14 -- 0.08 -- -4.14 1,2-Diethylbenzene 152.52 155.22 3.28 4.06 -- 0.08 -3.28 -4.06 Butylbenzene 156.07 155.98 4.06 4.27 -- 0.09 -4.06 -4.27 1,4-Diethylbenzene 155.71 155.22 3.73 4.06 -- 0.08 -3.73 -4.06 2-Propyltoluene 154.28 154.63 -- 4.14 -- 0.08 -- -4.14 1,2-Dimethyl-4-ethylbenzene 154.10 153.28 -- 3.99 -- 0.07 -- -3.99 1,2,3,4-Tetramethylbenzene 148.31 151.34 -- 3.92 -- 0.06 -- -4.00 1,2,4,5-Tetramethylbenzene -- 151.34 4.15 3.92 -- -0.36 -4.59 -4.14 7-Methyl-3-methylene-1,6- octadiene(myrcene) -- 174.13 -- 3.64 -- 0.15 -4.39 -3.64 (d)-Limonene 161.98 161.52 3.99 4.18 -- 0.11 -3.99 -4.18 (dl)-Limonene 162.19 161.52 4.26 4.18 -- 0.11 -4.26 -4.18 (l)-Limonene -- 161.52 3.99 4.18 -- 0.11 -3.99 -4.18 a-Pinene 158.97 158.93 4.74 4.76 -- 0.16 -4.74 -4.76 Decalin 154.30 155.19 5.19 5.19 -- 0.10 -5.19 -5.19 trans-Bicyclo[4.4.0]decane 157.10 155.19 5.19 5.19 -- 0.10 -5.19 -5.19 cis-Bicyclo[4.4.0]decane 154.12 155.19 5.19 5.19 -- 0.10 -5.19 -5.19 1-Decene 189.30 190.28 5.39 5.68 -- 0.17 -5.39 -5.68 n-Pentylcyclopentane 177.33 177.69 6.09 5.75 -- 0.14 -6.09 -5.75 tert-Butylcyclohexane 168.80 173.31 -- 5.07 -- 0.18 -- -5.07 1-Isopropyl-4-methylcyclohexane -- 176.24 5.70 5.36 -- 0.18 -5.70 -5.36 Isobutylcyclohexane 175.34 174.51 -- 5.34 -- 0.15 -- -5.34 Butylcyclohexane 175.56 175.37 -- 5.71 -- 0.13 -- -5.71 2,2,5,5-Tetramethylhexane 197.90 191.27 -- 5.73 -- 0.25 -- -5.73 2,2,4,5-Tetramethylhexane 193.59 191.62 -- 5.56 -- 0.23 -- -5.56 2,4,6-Trimethylheptane 196.80 192.82 -- 5.79 -- 0.20 -- -5.79 2,3,3,5-Tetramethylhexane 190.99 191.62 -- 5.56 -- 0.23 -- -5.56 2,5,5-Trimethylheptane 192.28 192.48 -- 5.93 -- 0.21 -- -5.93 2,2-Dimethyl-3-ethylhexane 192.28 192.48 -- 5.93 -- 0.21 -- -5.93 3,3,5-Trimethylheptane 191.51 192.48 -- 5.93 -- 0.21 -- -5.93 2,4-Dimethyloctane 194.92 193.68 -- 6.09 -- 0.19 -- -6.09 4,4-Dimethyloctane -- 193.33 -- 6.16 -- -- -4.81 -6.16 4-Propylheptane 193.33 194.54 -- 6.25 -- 0.18 -- -6.25 3,5-Dimethyloctane 193.07 193.68 -- 6.09 -- 0.19 -- -6.09 2,5-Dimethyloctane 194.92 193.68 -- 6.09 -- 0.19 -- -6.09 2,6-Dimethyloctane 195.45 193.68 -- 6.09 -- 0.19 -- -6.09 2,2,3,3-Tetramethylhexane 186.24 191.27 -- 5.73 -- 0.24 -- -5.73 2,7-Dimethyloctane 196.53 193.68 -- 6.09 -- 0.19 -- -6.09 2-Methyl-5-ethylheptane 194.39 193.68 -- 6.09 -- 0.19 -- -6.09

105

2,4-Dimethyl-4-ethylhexane 189.72 192.48 -- 5.93 -- 0.21 -- -5.93 3,4,4-Trimethylheptane 189.72 192.48 -- 5.93 -- 0.21 -- -5.93 3,6-Dimethyloctane 193.33 193.68 -- 6.09 -- 0.19 -- -6.09 3,3-Dimethyloctane 192.54 193.33 -- 6.16 -- 0.20 -- -6.16 3,4,5-Trimethylheptane 188.21 192.82 -- 5.79 -- 0.20 -- -5.79 3,4-Diethylhexane 189.47 193.68 -- 6.09 -- 0.19 -- -6.09 5-Methylnonane 194.12 194.54 -- 6.25 -- 0.18 -- -6.25 2-Methylnonane 195.99 194.54 -- 6.25 -- 0.18 -- -6.25 3-Methylnonane 194.92 194.54 -- 6.25 -- 0.18 -- -6.25 n-Decane 194.92 195.40 6.44 6.26 -- 0.17 -6.44 -6.26 Naphthalene -- 125.89 3.16 3.08 -0.15 -0.44 -3.62 -3.08 2-Methylnaphthalene -- 140.81 3.68 3.59 -- -0.07 -3.76 -3.59 1-Methylnaphthalene 138.73 140.81 3.74 3.59 -- 0.01 -3.74 -3.59 Pentylbenzene -- 172.25 4.64 4.86 -- 0.08 -4.64 -4.86 Pentamethylbenzene -- 166.26 3.73 4.43 -- -0.19 -3.98 -4.80 1-Undecene 205.73 206.55 -- 6.13 -- 0.15 -- -6.13 n-Hexylcyclopentane 193.60 193.96 -- 6.28 -- 0.13 -- -6.28 4-Methyldecane 211.23 210.81 -- 6.70 -- 0.15 -- -6.70 2-Methyldecane 210.94 210.81 -- 6.70 -- 0.15 -- -6.70 n-Undecane 211.23 211.67 7.55 6.64 -- 0.15 -7.55 -6.64 Biphenyl -- 151.65 3.96 3.83 -0.16 -0.37 -4.35 -4.70 Acenaphthene -- 142.89 3.96 3.72 -0.59 -0.63 -4.60 -3.82 2-Ethylnaphthalene -- 157.67 4.29 4.17 -- 0.02 -4.29 -4.17 1,8-Dimethylnaphthalene -- 155.73 4.42 4.10 -- -0.32 -4.76 -4.52 2,6-Dimethylnaphthalene -- 155.73 4.15 4.10 -- -0.73 -4.89 -4.52 1,3-Dimethylnaphthalene 159.09 155.73 4.29 4.10 -- 0.01 -4.29 -4.38 2,3-Dimethylnaphthalene -- 155.73 4.19 4.10 -- -0.68 -4.89 -4.52 1-Ethylnaphthalene 156.23 157.67 4.16 4.17 -- 0.02 -4.16 -4.17 2,7-Dimethylnaphthalene -- 155.73 4.27 4.10 -- -0.60 -4.89 -4.52 1,6-Dimethylnaphthalene 155.90 155.73 -- 4.10 -- 0.01 -- -4.38 1,4-Dimethylnaphthalene -- 155.73 3.72 4.10 -- -0.40 -4.14 -4.52 1,5-Dimethylnaphthalene -- 155.73 4.26 4.10 -- -0.48 -4.76 -4.52 Cyclohexylbenzene 168.69 167.73 -- 4.53 -- 0.04 -- -4.53 1,3-Diisopropylbenzene 189.58 189.07 -- 4.62 -- 0.11 -- -4.62 1,4-Diisopropylbenzene 189.36 189.07 -- 4.62 -- 0.12 -- -4.62 1,3,5-Triethylbenzene 188.48 187.01 7.06 5.15 -- 0.06 -7.06 -5.15 Hexylbenzene 188.48 188.52 5.26 5.42 -- 0.07 -5.26 -5.42 Hexamethylbenzene -- 181.18 4.83 4.94 -- -0.93 -5.84 -5.96 Bicyclohexyl 192.48 187.89 -- 5.71 -- 0.10 -- -5.71 1-Dodecene 222.07 222.82 -- 6.55 -- 0.13 -- -6.55

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n-Heptylcyclopentane 210.14 210.23 -- 6.77 -- 0.11 -- -6.77 n-Hexylcyclohexane 208.33 207.92 -- 6.80 -- 0.10 -- -6.80 n-Dodecane 227.42 227.94 7.66 6.99 -- 0.13 -7.66 -6.99 Fluorene -- 154.70 4.19 3.95 -0.62 -0.79 -4.99 -4.99 3-Methylbiphenyl 166.57 166.57 -- 4.34 -- 0.02 -- -5.36 Diphenylmethane -- 164.63 4.07 3.84 -- 0.01 -4.08 -3.94 Heptylbenzene -- 204.79 5.60 5.95 -- 0.06 -5.60 -5.95 1-Tridecene 238.37 239.09 -- 6.93 -- 0.12 -- -6.93 n-Heptylcyclohexane 224.85 224.19 -- 7.29 -- 0.09 -- -7.29 2-Methyldodecane 244.85 243.35 -- 7.50 -- 0.12 -- -7.50 n-Tridecane 243.88 244.21 7.59 7.30 -- 0.12 -7.59 -7.30 Anthracene -- 160.13 4.98 4.28 -1.91 -1.63 -6.61 -5.21 Phenanthrene -- 160.13 4.52 4.28 -0.40 -0.67 -5.19 -5.07 1-Methylfluorene -- 169.62 4.66 4.46 -0.56 -0.56 -5.22 -5.65 1,1-Diphenylethane 182.27 182.27 -- 4.30 -- 0.09 -- -4.59 Octylbenzene 222.35 221.06 6.46 6.44 -- 0.06 -6.46 -6.44 1,2-Dicyclohexylethane 222.89 220.43 -- 7.01 -- 0.07 -- -7.01 1,1-Dicyclohexylethane 218.38 219.57 -- 6.57 -- 0.09 -- -6.57 1-Tetradecene 254.71 255.36 -- 7.27 -- 0.10 -- -7.27 n-Nonylcyclopentane 243.03 242.77 -- 7.64 -- 0.09 -- -7.64 Cyclohexane,octyl- 241.25 240.46 -- 7.74 -- 0.08 -- -7.74 n-Tetradecane 260.03 260.48 7.96 7.57 -- 0.11 -7.96 -7.57 1-Methylphenanthrene -- 175.05 4.93 4.79 -- -0.93 -5.85 -5.72 9-Methylanthracene -- 175.05 5.33 4.79 -- -0.53 -5.87 -5.72 2-Methylanthracene -- 175.05 5.30 4.79 -- -1.65 -6.96 -5.86 1-Methylanthracene -- 175.05 5.28 4.79 -- -0.57 -5.85 -5.72 3-Methylphenanthrene -- 175.05 5.46 4.79 -- -0.38 -5.84 -5.72 Benzene,nonyl- 238.74 237.33 -- 6.89 -- 0.05 -- -6.89 1-Pentadecene 271.15 271.63 -- 7.58 -- 0.09 -- -7.58 n-Decylcyclopentane 259.45 259.04 -- 8.02 -- 0.08 -- -8.02 n-Nonylcyclohexane 257.86 256.73 -- 8.16 -- 0.07 -- -8.16 n-Pentadecane 276.59 276.76 9.45 7.81 -- 0.10 -9.45 -7.81 Pyrene -- 160.13 5.15 5.26 -0.85 -1.02 -6.18 -5.81 Fluoranthene -- 161.97 5.11 5.06 -0.76 -0.78 -5.89 -5.83 1,2,3,6,7,8-Hexahydropyrene -- 163.01 4.87 5.40 -- -1.08 -5.96 -6.13 1-Hexadecene 287.36 287.90 -- 7.86 -- 0.09 -- -7.86 n-Decylcyclohexane 274.03 273.00 -- 8.54 -- 0.07 -- -8.54 n-Hexadecane 292.95 293.03 8.40 8.01 0.58 0.09 -8.40 -8.01 2,3-Benzofluorene -- 188.93 5.90 5.15 -1.75 -1.83 -7.73 -7.00 Benzo(a)fluorene -- 188.93 5.10 5.15 -- -1.58 -6.68 -7.00

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n-Undecylbenzene 272.78 269.87 -- 7.69 -- 0.04 -- -7.69 1-Heptadecene 303.77 304.17 -- 8.09 -- 0.08 -- -8.09 n-Heptadecane 309.10 309.30 -- 8.17 -- 0.08 -- -8.19 Chrysene -- 194.36 5.92 5.48 -2.60 -2.14 -8.06 -7.22 Benz(a)anthracene -- 194.36 6.07 5.48 -- -1.31 -7.39 -7.08 Triphenylene -- 194.36 5.28 5.48 -1.77 -1.47 -6.74 -7.44 Naphthacene -- 194.36 5.44 5.48 -2.27 -2.74 -8.18 -7.36 Benzo(c)phenanthrene -- 194.36 7.48 5.48 -- -0.34 -7.82 -7.22 p-Terphenyl -- 211.65 5.16 5.78 -- -1.94 -7.11 -8.29 Dodecylbenzene 287.90 286.15 7.39 8.03 -- 0.04 -7.39 -8.03 1-Octadecene 320.01 320.44 -- 8.29 -- 0.07 -- -8.29 n-Dodecylcyclohexane 308.29 305.54 -- 9.19 -- 0.05 -- -9.19 n-Octadecane -- 325.57 7.52 8.30 -- -0.04 -7.63 -8.49 6-Methylchrysene -- 209.29 -- 6.00 -- -- -6.57 -7.88 Tridecylbenzene 304.29 302.42 -- 8.34 -- 0.04 -- -8.34 1-Nonadecene 336.50 336.71 -- 8.46 -- 0.06 -- -8.46 Tridecylcyclohexane 317.27 321.81 -- 9.46 -- 0.05 -- -9.50 Perylene -- 194.36 6.23 6.46 -2.52 -2.56 -8.80 -7.83 Benzo(b)fluoranthene -- 196.21 6.84 6.26 -- -1.38 -8.23 -7.86 Benzo(k)fluoranthene -- 196.21 6.72 6.26 -- -1.77 -8.50 -8.00 Benzo(a)pyrene -- 194.36 6.72 6.46 -1.60 -1.46 -8.19 -7.55 Benzo(e)pyrene -- 194.36 6.19 6.46 -- -1.40 -7.60 -7.69 Cholanthrene -- 211.37 6.35 6.12 -- -1.50 -7.86 -7.98 Eicosane -- 358.11 7.77 8.45 -- -0.34 -8.17 -8.96 3-Methylcholanthrene -- 226.29 6.39 6.64 -- -1.57 -7.97 -8.77 Indeno[1,2,3-cd]pyrene -- 196.21 7.82 7.24 -- -1.32 -9.16 -8.33 Benzo(ghi)perylene -- 194.36 6.76 7.44 -- -2.25 -9.03 -8.31 Dibenz(a,h)anthracene -- 228.60 5.76 6.69 -3.00 -2.29 -8.05 -9.39 Picene -- 228.60 4.89 6.69 -- -3.16 -8.05 -9.39 Benzo[b]chrysene -- 228.60 5.93 6.69 -- -2.50 -8.43 -9.39 Dibenz(a,j)anthracene -- 228.60 6.15 6.69 -- -2.27 -8.43 -9.39 Dibenz(a,c)anthracene -- 228.60 5.86 6.69 -- -2.38 -8.24 -9.39 Benzo(c)chrysene -- 228.60 -- 6.69 -- -- -7.81 -9.25

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SI Table 5. Experimental and calculated values of air-octanol partition coefficient, air- water partition coefficient and octanol-water partition coefficient

Compound logKao logKaw logKow Exp Calc Exp Calc Exp Calc Propadiene -- -1.27 -- 0.55 1.45 1.81 Propyne -1.29 -1.21 -0.35 0.14 0.94 1.34 Propylene -0.87 -1.35 0.90 0.91 1.77 2.26 Cyclopropane -0.21 -1.15 1.51 0.91 1.72 2.06 Propane -0.90 -1.40 1.46 1.74 2.36 3.14 2-Methylpropane -1.07 -1.62 1.69 1.64 2.76 3.26 n-Butane -1.30 -1.70 1.59 1.97 2.89 3.67 1,3-Butadiene -1.51 -1.54 0.48 0.70 1.99 2.24 2-Butyne -- -1.80 -- 0.43 1.46 2.23 2-Methylpropene -1.39 -1.56 0.95 0.92 2.34 2.48 1-Butene -1.42 -1.59 0.98 1.12 2.40 2.71 trans-2-Butene -1.34 -1.62 0.98 0.80 2.31 2.42 cis-2-Butene -1.34 -1.62 1.00 0.80 2.33 2.42 2-Methyl-2-butene -1.71 -1.98 0.96 0.74 2.67 2.72 Cyclopentane -2.21 -1.88 0.79 0.99 3.00 2.87 2,2-Dimethylpropane -0.93 -1.78 2.18 1.87 3.11 3.65 n-Pentane -1.68 -2.01 1.71 2.17 3.39 4.18 1,4-Pentadiene -1.79 -1.90 0.69 0.78 2.48 2.67 2-Methyl-1,3-butadiene -1.92 -1.93 0.50 0.42 2.42 2.36 1-Pentyne -1.97 -2.06 0.01 0.00 1.98 2.06 1,trans-3-Pentadiene -- -1.97 -- 0.53 2.44 2.50 cis-1,3-Pentadiene -- -1.97 -- 0.53 2.40 2.50 1,5-Hexadiene -2.11 -2.11 0.76 0.75 2.87 2.85 trans-1,3-Hexadiene -- -2.35 -- 0.70 3.16 3.04 trans-2,4-Hexadiene -- -2.43 -- 0.38 3.01 2.80 1-Hexyne -2.52 -2.47 0.21 0.19 2.73 2.66 Cyclohexene -2.59 -2.46 0.27 0.30 2.86 2.76 1-Hexene -2.16 -2.25 1.23 1.59 3.39 3.83 Methylcyclopentane -2.20 -2.27 1.17 1.28 3.37 3.56 Cyclohexane -2.65 -2.37 0.79 0.96 3.44 3.33 2,2-Dimethylbutane -2.03 -2.21 1.79 2.01 3.82 4.22 2,3-Dimethylbutane -1.74 -2.31 1.68 1.68 3.42 3.99 3-Methylpentane -1.76 -2.35 1.84 2.06 3.60 4.40 n-Hexane -2.03 -2.37 1.87 2.32 3.90 4.68 Benzene -2.77 -2.04 -0.64 -0.02 2.13 2.02

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1,4-Cyclohexadiene -- -2.42 -- -0.19 2.30 2.23 1,3-Cyclohexadiene -- -2.42 -- -0.19 2.47 2.23 1-Heptene -2.75 -2.63 1.24 1.74 3.99 4.38 Methylcyclohexane -2.37 -2.78 1.25 1.24 3.61 4.02 Cycloheptane -3.42 -2.96 0.58 0.83 4.00 3.79 n-Heptane -2.75 -2.75 1.91 2.41 4.66 5.16 Toluene -3.30 -2.67 -0.57 -0.19 2.73 2.49 Cycloheptatriene -3.36 -3.09 -0.73 -0.90 2.63 2.18 Ethylbenzene -3.64 -3.17 -0.49 -0.11 3.15 3.07 1,4-Dimethylbenzene -3.70 -3.27 -0.55 -0.29 3.15 2.99 1,3-Dimethylbenzene -3.73 -3.30 -0.53 -0.32 3.20 2.98 1,2-Dimethylbenzene -3.79 -3.30 -0.67 -0.32 3.12 2.98 (dl)-4-Vinyl-1-cyclohexene -3.67 -3.39 0.26 -0.01 3.93 3.38 2,4,4-Trimethyl-1-pentene -- -2.86 -- 1.28 4.55 4.13 1-Octene -3.16 -3.05 1.41 1.85 4.57 4.90 trans-2-Octene -- -3.17 -- 1.51 4.51 4.68 cis-2-Octene -- -3.17 -- 1.51 4.51 4.68 Ethylcyclohexane -3.47 -3.25 1.09 1.41 4.56 4.66 Cyclooctane -- -3.47 -- 0.83 4.45 4.30 n-Octane -3.06 -3.16 2.12 2.46 5.18 5.61 Styrene -3.90 -3.37 -0.95 -0.73 2.95 2.65 Cyclooctatetraene -- -3.68 -- -1.49 3.08 2.18 a-Methylstyrene -4.46 -4.05 -0.98 -1.04 3.48 3.01 trans-Methylstyrene -- -3.99 -- -0.99 3.35 3.01 Indane -5.27 -4.20 -2.09 -1.16 3.18 3.05 Isopropylbenzene -3.99 -3.52 -0.33 -0.15 3.66 3.37 Propylbenzene -4.06 -3.67 -0.37 0.06 3.69 3.73 3-Ethyltoluene -- -3.83 -- -0.27 3.98 3.56 4-Ethyltoluene -4.32 -3.83 -0.69 -0.27 3.63 3.56 2-Ethyltoluene -4.18 -3.83 -0.65 -0.27 3.53 3.56 1,3,5-Trimethylbenzene -3.87 -3.93 -0.45 -0.41 3.42 3.49 1,2,3-Trimethylbenzene -4.41 -3.96 -0.75 -0.48 3.66 3.48 1,2,4-Trimethylbenzene -4.23 -4.00 -0.60 -0.53 3.63 3.47 1-Nonene -3.64 -3.48 1.51 1.90 5.15 5.39 n-Nonane -3.51 -3.58 2.14 2.46 5.65 6.04 Indene -- -4.24 -- -1.70 2.92 2.54 1,2,3,4-Tetrahydronaphthalene -4.75 -4.85 -1.26 -1.28 3.49 3.57 1,3-Dimethyl-4-ethylbenzene -- -4.52 -- -0.46 4.47 4.06 1,2,3,5-Tetramethylbenzene -- -4.73 -- -0.66 4.10 3.98 tert-Butylbenzene -4.38 -3.91 -0.27 -0.12 4.11 3.79

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Isobutylbenzene -4.54 -4.09 0.14 -0.16 4.68 3.92 (dl)-sec-Butylbenzene -4.71 -4.02 -0.14 0.00 4.57 4.03 3-Isopropyltoluene -5.03 -4.18 -0.53 -0.33 4.50 3.86 4-Isopropyltoluene -4.45 -4.18 -0.35 -0.33 4.10 3.86 2-Isopropyltoluene -4.71 -4.18 -0.33 -0.33 4.38 3.86 1,3-Diethylbenzene -5.04 -4.34 -0.47 -0.20 4.57 4.14 3-Propyltoluene -- -4.36 -- -0.14 4.67 4.22 4-Propyltoluene -- -4.36 -- -0.14 4.60 4.22 1,2-Diethylbenzene -4.69 -4.34 -0.97 -0.20 3.72 4.14 Butylbenzene -4.57 -4.18 -0.19 0.17 4.38 4.35 1,3-Dimethyl-5-ethylbenzene -- -4.52 -- -0.46 4.55 4.06 1,4-Diethylbenzene -5.09 -4.34 -0.51 -0.20 4.58 4.14 2-Propyltoluene -- -4.36 -- -0.14 4.50 4.22 1,4-Dimethyl-2-ethylbenzene -- -4.52 -- -0.46 4.43 4.06 1,2-Dimethyl-4-ethylbenzene -- -4.52 -- -0.46 4.50 4.06 1,3-Dimethyl-2-ethylbenzene -- -4.52 -- -0.46 4.28 4.06 1,2-Dimethyl-3-ethylbenzene -- -4.52 -- -0.46 4.34 4.06 1,2,3,4-Tetramethylbenzene -- -4.73 -- -0.66 4.00 3.98 1,2,4,5-Tetramethylbenzene -- -4.39 -- -0.60 4.00 3.99 7-Methyl-3-methylene-1,6-octadiene(myrcene) -3.75 -4.07 0.42 -0.27 4.17 3.80 (d)-Limonene -4.27 -4.32 0.12 -0.03 4.38 4.29 (dl)-Limonene -4.27 -4.32 0.31 -0.03 4.57 4.29 (l)-Limonene -4.27 -4.32 0.12 -0.03 4.38 4.29 a-Pinene -3.36 -3.78 1.47 1.14 4.83 4.92 1-Decene -4.36 -3.94 1.35 1.91 5.70 5.85 tert-Butylcyclohexane -- -3.93 -- 1.32 5.04 5.25 1-Isopropyl-4-methylcyclohexane -3.70 -4.02 1.86 1.52 5.56 5.54 n-Decane -2.69 -4.03 2.32 2.40 5.01 6.43 Naphthalene -5.05 -3.86 -1.75 -1.22 3.30 3.10 2-Methylnaphthalene -5.53 -5.05 -1.67 -1.53 3.86 3.60 1-Methylnaphthalene -5.55 -5.13 -1.68 -1.53 3.87 3.60 Pentylbenzene -4.88 -4.71 0.02 0.23 4.90 4.94 Pentamethylbenzene -6.31 -5.46 -1.75 -0.86 4.56 4.48 Biphenyl -5.88 -5.83 -1.90 -1.49 3.98 3.85 Acenaphthene -6.04 -5.60 -2.12 -2.41 3.92 3.72 2-Ethylnaphthalene -6.04 -5.68 -1.66 -1.50 4.38 4.19 1,8-Dimethylnaphthalene -6.22 -5.87 -1.96 -1.67 4.26 4.12 2,6-Dimethylnaphthalene -- -5.46 -- -1.67 4.31 4.12 1,3-Dimethylnaphthalene -6.03 -6.14 -1.61 -1.75 4.42 4.11 2,3-Dimethylnaphthalene -5.83 -5.51 -1.43 -1.67 4.40 4.12

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1-Ethylnaphthalene -5.95 -5.68 -1.55 -1.50 4.40 4.19 2,7-Dimethylnaphthalene -- -5.59 -- -1.67 4.31 4.12 1,7-Dimethylnaphthalene -- -6.21 -- -1.67 4.44 4.12 1,6-Dimethylnaphthalene -- -6.14 -- -1.75 4.44 4.11 1,4-Dimethylnaphthalene -6.17 -5.79 -1.80 -1.67 4.37 4.12 1,5-Dimethylnaphthalene -6.22 -5.71 -1.84 -1.67 4.38 4.12 Hexylbenzene -5.45 -5.24 0.07 0.25 5.52 5.50 Hexamethylbenzene -6.61 -5.62 -1.50 -0.60 5.11 5.02 n-Dodecane -3.58 -4.96 2.52 2.16 6.10 7.12 Fluorene -6.59 -6.44 -2.41 -2.24 4.18 3.95 Diphenylmethane -6.42 -6.00 -2.28 -2.04 4.14 3.86 Heptylbenzene -5.58 -5.79 -0.21 0.22 5.37 6.01 Anthracene -7.09 -6.22 -2.64 -2.65 4.45 4.28 Phenanthrene -7.22 -7.15 -2.76 -2.75 4.46 4.28 1-Methylfluorene -7.54 -7.66 -2.57 -2.57 4.97 4.46 Octylbenzene -6.06 -6.36 0.24 0.14 6.30 6.50 n-Tetradecane -4.63 -5.93 2.58 1.74 7.20 7.68 1-Methylphenanthrene -7.78 -7.90 -2.70 -3.11 5.08 4.79 9-Methylanthracene -7.87 -8.30 -2.80 -3.11 5.07 4.79 2-Methylanthracene -6.59 -7.20 -1.59 -2.99 5.00 4.79 3-Methylphenanthrene -- -8.45 -- -3.11 5.15 4.79 Benzene,nonyl- -- -6.93 -- 0.02 7.11 6.94 Pyrene -8.19 -7.29 -3.31 -2.50 4.88 5.26 Fluoranthene -8.60 -7.83 -3.44 -2.77 5.16 5.06 2,3-Benzofluorene -9.57 -9.16 -3.80 -3.99 5.77 5.15 Benzo(a)fluorene -8.36 -9.41 -2.96 -3.99 5.40 5.15 n-Undecylbenzene -- -8.10 -- -0.36 8.14 7.73 Chrysene -9.48 -9.49 -3.67 -4.41 5.81 5.48 Benz(a)anthracene -9.07 -10.34 -3.31 -4.57 5.76 5.49 Triphenylene -10.69 -10.13 -5.20 -4.15 5.49 5.48 Naphthacene -10.45 -8.87 -4.69 -4.25 5.76 5.48 Benzo(c)phenanthrene -9.48 -11.29 -3.67 -4.41 5.81 5.48 p-Terphenyl -8.63 -9.88 -2.60 -3.53 6.03 5.78 Dodecylbenzene -- -8.69 -- -0.62 8.65 8.07 Tridecylbenzene -- -9.30 -- -0.91 9.36 8.38 Perylene -10.08 -9.53 -3.83 -4.26 6.25 6.46 Benzo(b)fluoranthene -10.35 -11.12 -4.57 -4.65 5.78 6.27 Benzo(k)fluoranthene -10.73 -10.69 -4.62 -4.47 6.11 6.27 Benzo(a)pyrene -10.86 -10.71 -4.73 -4.62 6.13 6.47 Benzo(e)pyrene -11.35 -10.73 -4.91 -4.44 6.44 6.47

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3-Methylcholanthrene -10.09 -13.52 -3.67 -6.31 6.42 6.64 Benzo(ghi)perylene -11.50 -10.34 -4.87 -4.28 6.63 7.45 Anthanthrene -- -10.55 -- -4.28 7.04 7.45 Dibenz(a,h)anthracene -11.78 -13.27 -5.03 -6.18 6.75 6.69 Pentacene -- -13.31 -- -5.95 7.11 6.69 Picene -- -12.41 -- -6.18 7.11 6.69 Benzo[b]chrysene -11.78 -13.06 -4.67 -6.18 7.11 6.69 Dibenz(a,j)anthracene -11.78 -13.29 -5.24 -6.18 6.54 6.69 Dibenz(a,c)anthracene -- -13.42 -- -6.40 6.41 6.69 Benzo(c)chrysene -- -13.10 -- -6.40 7.11 6.69 Dibenzo(c,g)phenanthrene -- -12.87 -- -6.18 7.11 6.69 Benzo(a)naphthacene -- -13.39 -- -6.40 6.81 6.69 Dibenzo(a,e)pyrene -- -14.04 -- -6.49 7.71 7.68 Dibenzo(a,l)pyrene -- -14.23 -- -6.49 7.71 7.68 Dibenzo(g,p)chrysene -- -15.63 -- -7.74 8.39 7.89

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REFERENCES

1. Baum EJ. Chemical property estimation : theory and application. Boca Raton:

Lewis Publishers; 1998.

2. Boethling RS, Mackay D. Handbook of property estimation methods for environmental chemicals : environmental and health sciences. Boca Raton: Lewis

Publishers; 2000.

3. Lyman WJR, W.; Rosenbalt, D. H. . Handbook of Chemical Property Estimations.

New York: McGraw-Hill Book Co.; 1982.

4. Reinhard M, Drefahl A, Knovel (Firm). Handbook for estimating physicochemical properties of organic compounds. In. Wiley; 1999. http://www.knovel.com/knovel2/Toc.jsp?BookID=1199.

5. Yaws CL. Yaws handbook of thermodynamic properties for hydrocarbons and chemicals. In. Knovel (Firm),; 2009. http://www.knovel.com/web/portal/browse/display?_EXT_KNOVEL_DISPLAY_bookid

=2380.

6. Bondi AA. Physical Properties of Molecular Crystals, Liquids, and Glasses.: New

York: John Wiley and Sons, Inc.; 1968.

7. Joback KG, Reid RC. Estimation of Pure-Component Properties from Group-

Contributions. Chem Eng Commun. 1987;57(1-6):233-43.

114

8. Hukkerikar AS, Sarup B, Ten Kate A, Abildskov J, Sin G, Gani R. Group- contribution(+) (GC(+)) based estimation of properties of pure components: Improved property estimation and uncertainty analysis. Fluid Phase Equilibr. 2012;321:25-43.

9. Lian B, Yalkowsky SH. Molecular Geometry and Melting Point Related

Properties. Ind Eng Chem Res. 2012;51(51):16750-4. doi: 10.1021/ie302574y.

10. Lian B, Yalkowsky SH. Molecular geometry and boiling related thermodynamic properties. J Chem Thermodyn. 2012;54:250-3.

11. Lian B, Yalkowsky SH. A simplified approach to predict the heat of melting for organic compounds. Chemometr Intell Lab. 2011;108(2):150-3.

12. Sanghvi R, Yalkowsky SH. Estimation of the normal boiling point of organic compounds. Ind Eng Chem Res. 2006;45(8):2856-61. doi: Doi 10.1021/Ie051277g.

13. Jain A, Yalkowsky SH. Estimation of melting points of organic compounds-II. J

Pharm Sci-Us. 2006;95(12):2562-618. doi: Doi 10.1002/Jps.20634.

14. Johnson JLH, Yalkowsky SH. Two new parameters for predicting the entropy of melting: Eccentricity (epsilon) and spirality (mu). Ind Eng Chem Res. 2005;44(19):7559-

66. doi: Doi 10.1021/Ie050055f.

15. Jain A, Yang G, Yalkowsky SH. Estimation of melting points of organic compounds. Ind Eng Chem Res. 2004;43(23):7618-21. doi: Doi 10.1021/Ie049378m.

16. Zhao LW, Ni N, Yalkowsky SH. A modification of Trouton's rule by simple molecular parameters for hydrocarbon compounds. Ind Eng Chem Res. 1999;38(1):324-7.

115

17. Jain N, Yalkowsky SH. UPPER III: Unified physical property estimation relationships. Application to non-hydrogen bonding aromatic compounds. J Pharm Sci-

Us. 1999;88(9):852-60.

18. Dannenfelser RM, Yalkowsky SH. Predicting the total entropy of melting:

Application to pharmaceuticals and environmentally relevant compounds. J Pharm Sci-

Us. 1999;88(7):722-4.

19. Myrdal PB, Krzyzaniak JF, Yalkowsky SH. Modified Trouton's rule for predicting the entropy of boiling. Ind Eng Chem Res. 1996;35(5):1788-92.

20. Jain A, Yang G, Yalkowsky SH. Estimation of total entropy of melting of organic compounds. Ind Eng Chem Res. 2004;43(15):4376-9.

21. Mishra DS, Yalkowsky SH. Estimation of Entropy of Vaporization - Effect of

Chain-Length. Chemosphere. 1990;21(1-2):111-7.

22. Leo AJ. Calculating Log P(Oct) from Structures. Chem Rev. 1993;93(4):1281-

306.

23. NIST Chemistry WebBook, NIST Standard Reference Database Number 69 Eds.

P.J. Linstrom and W.G. Mallard, National Institute of Standards and Technology,

Gaithersburg MD, 20899, http://webbook.nist.gov,.

24. US EPA. 2009 Estimation Programs Interface Suite™ for Microsoft® Windows, v 4.00 United States Environmental Protection Agency, Washington, DC, USA.

25. Jia QZ, Wang QA, Ma PS. Prediction of the Enthalpy of Vaporization of Organic

Compounds at Their Normal Boiling Point with the Positional Distributive Contribution

Method. J Chem Eng Data. 2010;55(12):5614-20. doi: Doi 10.1021/Je1004824.

116

26. Acree W, Chickos JS. Phase Transition Enthalpy Measurements of Organic and

Organometallic Compounds. Sublimation, Vaporization and Fusion Enthalpies From

1880 to 2010. J Phys Chem Ref Data. 2010;39(4).

27. Admire B, Yalkowsky SH. Predicting the octanol solubility of organic compounds. J Pharm Sci-Us. 2013:n/a-n/a. doi: 10.1002/jps.23561.

28. Yalkowsky SH, He Y, Jain P. Handbook of aqueous solubility data. 2nd ed. Boca

Raton, FL: CRC Press; 2010.

29. Yalkowsky SH. Solubility and solubilization in aqueous media. Washington, D.C.

New York ; Oxford: American Chemical Society ;

Oxford University Press; 1999.

30. The Merck index. Cambridge, MA: CambridgeSoft.; Available from: http://www.library.arizona.edu/search/articles/dbDetail.php?shortname=merck.

31. Grant DJW, Mehdizadeh M, Chow AHL, Fairbrother JE. Non-Linear Vanthoff

Solubility Temperature Plots and Their Pharmaceutical Interpretation. Int J Pharmaceut.

1984;18(1-2):25-38.

32. Boethling RS, Howard PH, Meylan WM. Finding and estimating chemical property data for environmental assessment. Environ Toxicol Chem. 2004;23(10):2290-

308.

33. Hildebrand JH, Scott RL. The solubility of nonelectrolytes. 3d ed. New York,:

Reinhold Pub. Corp.; 1950.

117

34. Myrdal PB, Yalkowsky SH. Estimating pure component vapor pressures of

complex organic molecules. Ind Eng Chem Res. 1997;36(6):2494-9.

35. Hildebrand JH, Prausnitz JM, Scott RL. Regular and related solutions; the solubility of gases, liquids, and solids. New York,: Van Nostrand Reinhold Co.; 1970.