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Revised Group Additivity Values for Enthalpies of Formation (At 298 K) of Carbon– Hydrogen and Carbon–Hydrogen–Oxygen Compounds

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Revised Group Additivity Values for Enthalpies of Formation (At 298 K) of Carbon– Hydrogen and Carbon–Hydrogen–Oxygen Compounds Revised Group Additivity Values for Enthalpies of Formation (at 298 K) of Carbon– Hydrogen and Carbon–Hydrogen–Oxygen Compounds Cite as: Journal of Physical and Chemical Reference Data 25, 1411 (1996); https://doi.org/10.1063/1.555988 Submitted: 17 January 1996 . Published Online: 15 October 2009 N. Cohen ARTICLES YOU MAY BE INTERESTED IN Additivity Rules for the Estimation of Molecular Properties. Thermodynamic Properties The Journal of Chemical Physics 29, 546 (1958); https://doi.org/10.1063/1.1744539 Critical Evaluation of Thermochemical Properties of C1–C4 Species: Updated Group- Contributions to Estimate Thermochemical Properties Journal of Physical and Chemical Reference Data 44, 013101 (2015); https:// doi.org/10.1063/1.4902535 Estimation of the Thermodynamic Properties of Hydrocarbons at 298.15 K Journal of Physical and Chemical Reference Data 17, 1637 (1988); https:// doi.org/10.1063/1.555814 Journal of Physical and Chemical Reference Data 25, 1411 (1996); https://doi.org/10.1063/1.555988 25, 1411 © 1996 American Institute of Physics for the National Institute of Standards and Technology. Revised Group Additivity Values for Enthalpies of Formation (at 298 K) of Carbon-Hydrogen and Carbon-Hydrogen-Oxygen Compounds N. Cohen Thermochemical Kinetics Research, 6507 SE 31st Avenue, Portland, Oregon 97202-8627 Received January 17, 1996; revised manuscript received September 4, 1996 A program has been undertaken for the evaluation and revision of group additivity values (GAVs) necessary for predicting, by means of Benson's group additivity method, thermochemical properties of organic molecules. This review reports on the portion of that program dealing with GAVs for enthalpies of formation at 298.15 K (hereinafter abbreviated as 298 K) for carbon-hydrogen and carbon-hydrogen-oxygen compounds. A complete database of experimental data for gas, liquid, and crystal (solid) phase en­ thalpies of formation is presented. The GAV s, ring strain corrections, and non-nearest neighbor interactions derived from the database are presented in tabular form, together with a description of their evaluation and comments on reliability, uncertainties, and missing or questionable data. © 1996 American Institute of Physics and American rhp.mirni Sndp.ty. Key words: enthalpy of formation; estimation; group additivity; organic compounds; thermochemical properties. Contents and engineers. It is also accepted that the range of molecules 1. Introduction................................ 1411 of possible interest will, for the foreseeable future, exceed by 2. Results and Procedure ....................... 1411 orders of magnitude the number of compounds that can be 2.1. Enthalpies of Formation.................. 1411 measured in the laboratory. Hence, simple but reliable tech­ 2.2. Group Additivity: A Brief Description ...... 1412 niques are desirable for estimating thermochemical proper­ 2.3. Procedure.............................. 1413 ties of species for which experimental data are not available. 2.4. The Database........................... 1413 A number of methods have been developed in recent years; 2.5. Format of the Tables ..................... 1414 while there is not unanimous agreement regarding the best 2.6. Questionable and Undetermined Group method, it seems generally agreed that one of the best (if not Values ................................ 1415 the best) is that of group additivities, especially as developed 2.7. Non-Nearest Neighbor Interactions ......... 1415 by Benson and co-workers.! Not only is the method fairly 2.8. Summary and Conclusions ................ 1417 easy to apply, but it usually can estimate properties with an 3. Tables of C-H-O Compounds ................ 1418 uncertainty no larger than typical experimental uncertainties. 4. Acknowledgments .......................... 1481 In addition to containing a description of the method, Ref. 1 5. References ................................. 1481 tabulates the best ~yailable gr.oup additivity values (GAVs) for gas phase properties as of 1976. List of Tables Under a contract from the National Institute of Standards 1. Group additivity values for enthalpy of formation and Technology (NIST), we have undertaken a program for (298 K), C-H-O groups ..................... 1418 the evaluation and revision of GA Vs necessary for predict­ 2. Comparison of group additivity values, Enthalpy ing, by means of Benson's method, thermochemical proper­ of formation (298 K) ........................ 1432 ties of organic molecules. 3. Carbon-hydrogen compounds: Enthalpy of formation (298 K) .......................... 1435 ·2. Results and Procedure 4 Carbon-hydrogen compounds (C.,H, 0)' Enthalpy of formation (298 K) .... : ........... 1452 2.1. Enthalpies of Formation (C 5. Carbon-hydrogen compounds r H,,02): Numerous tabulations of thermochemical properties (in­ Enthalpy of formation (298 K) .... : ........... 1461 cluding enthalpies of formation, 11tH) of organic compounds 6. Carbon-hydrogen compounds (Cr H"On>2): have been published. The starting point for most subsequent Enthalpy of formation (298 K) .... : ........... 1472 tabulations has been "Selected Values of Physical and Ther­ modynamic Properties of Hydrocarbons and Related Com­ 1. Introduction pounds," by Rossini et al. 2 However, this compilation com­ bined experimental values with calculated and extrapolated The importance of reliable and conveniently accessible ones in a manner that did not always make clear which were thermochemical data (enthalpies of formation, entropies, and which. Stull, Westrum, and Sinke (SWS)3 perpetuated this heat capacities) is universally accepted among both scientists uncertainty in their tabulations of thermochemical properties 0047-2689/96/25(6)11411nll$18.00 1411 J. Phys. Chern. Ref. Data, Vol. 25, No.6, 1996 1412 N.COHEN in the now-familiar JANAF-like format. These important ref­ chemical properties of organic compounds to a set of bond erences have been cited as primary sources in more recent and group energies. In 1958, Benson and Buss lO discussed a compilations, so that now one is often hard-pressed to deter­ hierarchy of additivity schemes, and established a conceptual mine to what extent a particular compilation is dependent on framework that provided a physical justification for the nonexperimental values. This issue gains in importance approachY In this hierarchy, atomic additivity is the first when one tries to develop empirical methods for predicting level of approximation; the second and third are bond addi­ thermochemical properties, as in the group additivity tivity and group additivity, respectively. Atomic additivity method; if all the Rossini and SWS values are thrown into (i.e., a particular molecular property can be evaluated as the the hopper, one in effect is fitting to already fitted values. sum of contributions from the constituent atoms) is valid for 4 Cox and Pilcher began a program to establish the experi­ such simple properties as molecular weights, but certainly mental database anew, and to clarify the question of what not for thermochemical properties. Bond additivity (i.e., a exactly has been measured and what has not. That study molecular property is the sum of contributions from each culminated in the monograph by Pedley et at., Thennochemi­ bond in the molecule) thus constitutes the first nontrivial cal Data of Organic Compounds5 (PNK). That compilation level in the Benson and Buss hierarchical scheme, and can is still the soundest starting point for any compilation of often provide useful estimations. experimental enthalpy of formation data. 6 A group is defined by Benson 12 as "a polyvalent atom Several workers have turned to Benson's group additivity (ligancy ~2) in a molecule together with all of its ligands." method for predicting thermochemical properties. An exem­ A group is written as X-(A)/B)/C)k(D)/, where X is the plary model is Stein's computer program, available through central atom attached to i A atoms, j B atoms, etc. In the NIST. 7 However, such programs and projects often build on present discussion only C, H, and 0 atoms are considered, so previous evaluations in a way that does not always ensure that X is necessarily a carbon or oxygen atom. Several dif­ mutual consistency of all of the separate parts of the evalu­ ferent types of C atoms are distinguished and notated dis­ ation. For example, most group values are derived in step­ tinctly: sp3 (C), sp2 (Cd), sp (C ), aromatic Sp2 (C ), fused wise fashion, starting with groups of the alkanes. If the al­ t b ring aromatic (C ), and allenic carbon, =C= (C ). C can kane group values are updated, almost all other group values bi a bi C C . C will be affected. There is thus a clear need to reestablish a be bonded only to b or bi a is necessarily bonded to two uniformly derived set of GAV evaluations. Hence, the moti­ Cd atoms. Two oxygen-containing group families in which vation for the present project. the central "atom" is polyatomic are defined: carbonyl Our approach was similar to that of others in that we be­ (>C=O) and >C=C=O, both of which have two variable gan by deriving GAVs for the alkane groups using as a da­ ligands. tabase all the alkanes themselves.s The alkane groups, to­ In addition, there are corrections for nonbonded interac­ gether with the derived values for all three phases. are shown tions that are required because of spatial interactions that are in the first section of Table 1. With these values fixed, we not defined in terms of a series of chemical bonds: the most then turned to all
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