Polycyclic Aromatic Hydrocarbons (Pahs)
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Reactivity and Functionalization of Naphthalene and Anthracene Complexes of {Tpw(NO)(Pme3)}
Reactivity and Functionalization of Naphthalene and Anthracene Complexes of {TpW(NO)(PMe3)} Laura Jessica Strausberg Baltimore, Maryland B.A., Hollins University, 2008 A Dissertation presented to the Graduate Faculty of the University of Virginia in Candidacy for the Degree of Doctor of Philosophy Department of Chemistry University of Virginia July, 2013 ii Abstract Chapter 1 introduces the organic chemistry of aromatic hydrocarbons, with attention paid to regiochemical outcomes of organic reactions. The binding of naphthalene and anthracene to metal complexes is discussed, along with organic transformations they undergo as a result of their complexation. The previous work on osmium and rhenium complexes of naphthalene from the Harman group is explored. Finally, some spectroscopic techniques for exploring the chemistry of {TpW(NO)(PMe3)} complexes of naphthalene and anthracene are introduced. Chapter 2 discusses the highly distorted allyl complexes formed from {TpW(NO)(PMe3)} and the exploration of their origin. Attempts at stereoselectively deprotonating these cationic complexes is also discussed. 2 Chapter 3 describes our study of TpW(NO)(PMe3)(3,4-η -naphthalene)’s ability to undergo a Diels-Alder reaction with N-methylmaleimide. A solvent study suggested that this reaction proceeds by a concerted mechanism. To probe the mechanism further, we synthesized a series of methylated and methoxylated naphthalene complexes and measured their rates of reaction with N-methylmaleimide compared to the parent complex. We found that 1- substitution on the naphthalene increased the rate of cycloaddition, even if the substituent was in the unbound ring, while 2-substitution slowed the reaction rate when in the bound ring. This information is consistent with a concerted mechanism, as a 2-substituted product would be less able to isomerize to form the active isomer for the cycloaddition to occur. -
Crystal Structure of Methyl 10-(Pyridin-4-Yl)-Anthracene-9
Z. Kristallogr. NCS 2018; 233(3): 441–443 Xiang Huang and Da-Bin Shi* Crystal structure of methyl 10-(pyridin-4-yl)- anthracene-9-carboxylate, C21H15NO2 Table 1: Data collection and handling. Crystal: Block, colorless Size: 0.30 × 0.20 × 0.10 mm Wavelength: Mo Kα radiation (0.71073 Å) µ: 0.09 mm−1 Diffractometer, scan mode: Bruker SMART, φ and ω-scans θmax, completeness: 27.6°, >99% N(hkl)measured, N(hkl)unique, Rint: 9199, 3516, 0.027 Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2700 N(param)refined: 218 Programs: Bruker programs [1], SHELX [2, 3] before stirring for 2 h at 65 °C. Crude 10-bromo-anthracene- 9-carboxylic acid was precipitated by adding the acetic acid solution to 800 mL of ice/water slush, followed by suc- https://doi.org/10.1515/ncrs-2017-0334 tion filtration. The residue on the filter was dissolved in Received October 31, 2017; accepted February 20, 2018; available 500 mL of a 5% aquaeus solution of K2CO3 followed by online March 6, 2018 gravity filtration to remove undissolved side products such as 9,10-dibromoanthracene. The filtrate was acidified with Abstract concentrated HCl to precipitate crude 10-bromo-anthracene- Aba a = C21H15NO2, orthorhombic, 2 (no. 41), 22.149(2) Å, 9-carboxylic acid, which was recrystallized from 100 mL b = c = V = 3 Z = 13.2899(12) Å, 10.6679(10) Å, 3140.2(5) Å , 8, ethanol to yield 5.76 g of yellow needles. R F = wR F2 = T = gt( ) 0.0418, ref( ) 0.0953, 296(2) K. -
ORGANIC CHEMISTRY- I (Nature of Title Bonding and Stereochemistry) Module No
Subject Chemistry Paper No. and Paper 1: ORGANIC CHEMISTRY- I (Nature of Title Bonding and Stereochemistry) Module No. and Module 8: Aromaticity of fused rings Title Module Tag CHE_P1_M8 CHEMISTRY PAPER 1: ORGANIC CHEMISTRY- I(Nature of Bonding and Stereochemistry) MODULE 8: Aromaticity of fused rings TABLE OF CONTENT 1. Learning Outcomes 2. Introduction 3. Classification of fused ring systems 4. Aromaticity in fused ring systems 4.1. Aromaticity of some benzenoid fused systems 4.1.1. Naphthalene 4.1.2. Anthracene 4.1.3. Phenanthrene 4.1.4. Resonance energy of fused ring systems 4.2. Aromaticity of some non-benzenoid fused systems 4.2.1. Azulenes 4.2.2. Oxaazulenaones 5. Other fused ring systems 5.1. Phenalene 5.2. Benzo cyclobutadiene 5.3. Ferrocene 6. Summary CHEMISTRY PAPER 1: ORGANIC CHEMISTRY- I(Nature of Bonding and Stereochemistry) MODULE 8: Aromaticity of fused rings 1. Learning Outcomes After studying this module, you shall be able to: Learn about the fused rings Understand that how fused rings are classified Learn about the aromaticity of the fused rings Understand aromaticity in the benzenoid and non-benzenoid fused ring systems Learn about some other special cases 2. Introduction As you are already aware that the aromatic compounds apparently contain alternate double and single bonds in a cyclic structure and resemble benzene in chemical behavior. Up till now we have discussed the aromaticity in monocyclic rings. In this module, we shall discuss about the aromaticity of fused rings. So, before starting with the aromaticity of fused rings first we should know what fused rings are. -
Mild Synthesis of Perylene Tetracarboxylic Monoanhydrides with Potential Applications in Organic Optoelectronics
City University of New York (CUNY) CUNY Academic Works All Dissertations, Theses, and Capstone Projects Dissertations, Theses, and Capstone Projects 5-2019 Mild Synthesis of Perylene Tetracarboxylic Monoanhydrides with Potential Applications in Organic Optoelectronics Xizhe Zhao The Graduate Center, City University of New York How does access to this work benefit ou?y Let us know! More information about this work at: https://academicworks.cuny.edu/gc_etds/3258 Discover additional works at: https://academicworks.cuny.edu This work is made publicly available by the City University of New York (CUNY). Contact: [email protected] Mild Synthesis of Perylene Tetracarboxylic Monoanhydrides with Potential Applications in Organic Optoelectronics By Xizhe Zhao A dissertation submitted to the Graduate Faculty in Chemistry in partial fulfillment of the requirements for the degree of Doctor of Philosophy The City University of New York. 2019 © 2019 Xizhe Zhao All Rights Reserved ii Mild Synthesis of Perylene Tetracarboxylic Monoanhydrides with Potential Applications in Organic Optoelectronics by Xizhe Zhao This manuscript has been read and accepted for the Graduate Faculty in Chemistry in satisfaction of the dissertation requirement for the degree of Doctor of Philosophy. 04/29/19 Prof. Shi Jin _________________________ __________________________________________________ Date Chair of Examining Committee 04/29/19 Prof. Brian R. Gibney _________________________ __________________________________________________ Date Executive Officer Supervisory Committee: Prof. Krishnaswami Raja Prof. Sanjai Kumar Pathak THE CITY UNIVERSITY OF NEW YORK iii ABSTRACT Mild Synthesis of Perylene Tetracarboxylic Monoanhydrides with Potential Applications in Organic Optoelectronics By Xizhe Zhao Advisor: Professor Shi Jin Perylene tetracarboxylic derivatives are considered good n-type semi-conductors. In past decades, there has been extensive study on their synthesis and electronic properties. -
Polycyclic Aromatic Hydrocarbon Structure Index
NIST Special Publication 922 Polycyclic Aromatic Hydrocarbon Structure Index Lane C. Sander and Stephen A. Wise Chemical Science and Technology Laboratory National Institute of Standards and Technology Gaithersburg, MD 20899-0001 December 1997 revised August 2020 U.S. Department of Commerce William M. Daley, Secretary Technology Administration Gary R. Bachula, Acting Under Secretary for Technology National Institute of Standards and Technology Raymond G. Kammer, Director Polycyclic Aromatic Hydrocarbon Structure Index Lane C. Sander and Stephen A. Wise Chemical Science and Technology Laboratory National Institute of Standards and Technology Gaithersburg, MD 20899 This tabulation is presented as an aid in the identification of the chemical structures of polycyclic aromatic hydrocarbons (PAHs). The Structure Index consists of two parts: (1) a cross index of named PAHs listed in alphabetical order, and (2) chemical structures including ring numbering, name(s), Chemical Abstract Service (CAS) Registry numbers, chemical formulas, molecular weights, and length-to-breadth ratios (L/B) and shape descriptors of PAHs listed in order of increasing molecular weight. Where possible, synonyms (including those employing alternate and/or obsolete naming conventions) have been included. Synonyms used in the Structure Index were compiled from a variety of sources including “Polynuclear Aromatic Hydrocarbons Nomenclature Guide,” by Loening, et al. [1], “Analytical Chemistry of Polycyclic Aromatic Compounds,” by Lee et al. [2], “Calculated Molecular Properties of Polycyclic Aromatic Hydrocarbons,” by Hites and Simonsick [3], “Handbook of Polycyclic Hydrocarbons,” by J. R. Dias [4], “The Ring Index,” by Patterson and Capell [5], “CAS 12th Collective Index,” [6] and “Aldrich Structure Index” [7]. In this publication the IUPAC preferred name is shown in large or bold type. -
Estimation of Enthalpy of Bio-Oil Vapor and Heat Required For
Edinburgh Research Explorer Estimation of Enthalpy of Bio-Oil Vapor and Heat Required for Pyrolysis of Biomass Citation for published version: Yang, H, Kudo, S, Kuo, H-P, Norinaga, K, Mori, A, Masek, O & Hayashi, J 2013, 'Estimation of Enthalpy of Bio-Oil Vapor and Heat Required for Pyrolysis of Biomass', Energy & Fuels, vol. 27, no. 5, pp. 2675-2686. https://doi.org/10.1021/ef400199z Digital Object Identifier (DOI): 10.1021/ef400199z Link: Link to publication record in Edinburgh Research Explorer Document Version: Early version, also known as pre-print Published In: Energy & Fuels General rights Copyright for the publications made accessible via the Edinburgh Research Explorer is retained by the author(s) and / or other copyright owners and it is a condition of accessing these publications that users recognise and abide by the legal requirements associated with these rights. Take down policy The University of Edinburgh has made every reasonable effort to ensure that Edinburgh Research Explorer content complies with UK legislation. If you believe that the public display of this file breaches copyright please contact [email protected] providing details, and we will remove access to the work immediately and investigate your claim. Download date: 04. Oct. 2021 Estimation of Enthalpy of Bio-oil Vapor and Heat Required for Pyrolysis of Biomass Hua Yang,† Shinji Kudo,§ Hsiu-Po Kuo,‡ Koyo Norinaga, ξ Aska Mori, ξ Ondřej Mašek,|| and Jun-ichiro Hayashi †, ξ, §, * †Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, -
ALABAMA SEAFOOD SURVEILLANCE SAMPLES NPH = Naphthalene, FLU = Fluorene, PHN = Phenanthrene, ANT = Anthracene, FLA = Fluoranthene
ALABAMA SEAFOOD SURVEILLANCE SAMPLES NPH = Naphthalene, FLU = Fluorene, PHN = Phenanthrene, ANT = Anthracene, FLA = Fluoranthene, Polycyclic Aromatic Hydrocarbon (PAH) and PYR = Pyrene, BaA = Benz(a)anthracene, CHR = Chrysene, BbF = Benzo(b)fluoranthene, DOSS Results Summary BkF = Benzo(k)fluoranthene, BaP = Benzo(a)pyrene, DBA = Dibenz(a,h)anthracene, IcdPy = Indeno(1,2,3-cd)pyrene, DOSS = Dioctylsulfosuccinate **The estimated maximum total PAH value represents a "worst case" estimate of the PAHs including alkyl homologs that could potentially be in the that happens to yield fluorescence responsesample. Results reported using FDACS Screening Method 521, based on It may include fluorescent compounds other than PAHs and background signal that happens to yield fluorescence response FDA LC Fluorescence Screening Method and FDACS DOSS Levels of Concern bases on FDA's Protocol for Interpretation and Use of Sensory Testing and Analytical Chemistry Results for Reopening In order to "PASS" Method 522 based on FDA's Determination of Levels of Concern (ppm) Oil-Impacted Areas closed to Seafood Harvesting. 7/26/10 samples must not Dioctylsulfosuccinate in Select Seafoods using LC/MS Shrimp and Crab 123 246 1846 246 185 1.32 1.32 13.2 0.132 0.132 1.32 61.5 500 exceed any Sorted by seafood type (crab, finfish, oyster, shrimp), Oysters 133 267 2000 267 200 1.43 143 1.43 14.3 0.143 0.143 1.43 66.5 500 FDA Levels of harvest area and sample # Finfish 32.7 65.3 490 65.3 49 0.35 35 0.35 0.35 0.035 0.035 0.35 16.35 100 Concern <LOD = less than Limit of Detection, -
Chapter 16 Liquid and Solids
Homework #2 Chapter 16 Liquid and Solids 7. Vapor Pressure: The pressure exerted by the vapor of a liquid when the vapor and the liquid are in dynamic equilibrium. The vapor pressure reflects the fact that within a system there is a distribution of energies that molecules can have, therefore, some molecules will have enough energy to overcome the intermolecular forces and enter into the gas phase. All liquids have some vapor pressure. The stronger the intermolecular forces the smaller the vapor pressure. All solids also have a vapor pressure. This is why if you leave ice in the freezer for a long time it “disappears.” The vapor pressure of solids is less than the vapor pressure of liquids. As the temperature increases the molecules have more energy, therefore, more molecules can escape into the gas phase (vapor pressure increases). When the vapor pressure is equal to the atmospheric pressure the solution boils. 9. a) Surface Tension As the intermolecular forces increase (↑), surface tension increases (↑). b) Viscosity As the intermolecular forces increase (↑), the viscosity increases (↑). c) Melting Point As the intermolecular forces increase (↑), the melting point increases (↑). d) Boiling Point As the intermolecular forces increase (↑), the boiling point increases (↑). e) Vapor Pressure As the intermolecular forces increase (↑), the vapor pressure decreases (↓). 11. Intermolecular Forces: The forces of attraction/repulsion between molecules. Intramolecular Forces: The forces of attraction/repulsion within a molecule. Intramolecular forces are stronger the intermolecular forces. Types of intermolecular forces: Dipole-Dipole Forces: The interaction between two electric dipoles in different molecules. Hydrogen Bonding: The attraction between a hydrogen atom (that is bonded to an O, N, or F atom) and an O, N, or F atom in a neighboring molecule. -
Azulene—A Bright Core for Sensing and Imaging
molecules Review Azulene—A Bright Core for Sensing and Imaging Lloyd C. Murfin * and Simon E. Lewis Department of Chemistry, University of Bath, Bath BA2 7AY, UK; [email protected] * Correspondence: lloyd.murfi[email protected] Abstract: Azulene is a hydrocarbon isomer of naphthalene known for its unusual colour and fluores- cence properties. Through the harnessing of these properties, the literature has been enriched with a series of chemical sensors and dosimeters with distinct colorimetric and fluorescence responses. This review focuses specifically on the latter of these phenomena. The review is subdivided into two sec- tions. Section one discusses turn-on fluorescent sensors employing azulene, for which the literature is dominated by examples of the unusual phenomenon of azulene protonation-dependent fluorescence. Section two focuses on fluorescent azulenes that have been used in the context of biological sensing and imaging. To aid the reader, the azulene skeleton is highlighted in blue in each compound. Keywords: fluorescence; azulene; sensor; dosimeter; bioimaging; chemosensor; chemodosimeter 1. Introduction Azulene, 1, is an isomer of naphthalene, 2, composed of fused 5- and 7-membered ring systems (Figure1) and named for its vibrant blue colour. Unlike naphthalene, azulene is a non-alternant hydrocarbon, possessing nodal points at C-2 and C-6 of the HOMO and C-1 and C-3 of the LUMO [1]. The location of these nodes results in low electronic repulsion in the S1 singlet excited state, affording a relatively small HOMO-LUMO gap. Hence, the S0!S1 transition arises from absorption in the visible region. Conversely, in naphthalene, coefficient magnitudes remain consistent for each position in both the HOMO Citation: Murfin, L.C.; Lewis, S.E. -
Determination of Petroleum Hydrocarbons in Sediments
UNITED NATIONS ENVIRONMENT PROGRAMME NOVEMBER 1992 Determination of petroleum hydrocarbons in sediments Reference Methods For Marine Pollution Studies No. 20 Prepared in co-operation with IOC IAEA UNEP 1992 ~ i - PREFACE The Regional Seas Programme was initiated by UNEP in 1974. Since then the Governing Conncil ofUNEP has repeatedly endorsed a regional approach to the control of marine pollution and the management of marine and coastal resources and has requested the development of regional action plans. The Regional Seas Progranune at present includes ten regions and has over 120 coastal States participating in it (1),(2). One of the basic components of the action plans sponsored by UNEP in the framework of the Regional Seas Programme is the assessment of the state of the marine em~ronment and of its resources, and of the sources and trends of the pollution, and the impact of pollution on human health, marine ecosystems and amenities. In order to assist those participating in this activity and to ensure that the data obtained through this assessment can be compared. on a world-wide basis and thns contribute to the Global Environment Monitoring System (GEMS) of UNEP, a set of Reference Methods and Guidelines for marine pollution studies is being developed as part of a programme of c9mprehensive technical support which includes the provision of expert advice, reference methods and materials, training and data quality assurance (3). The Methods are recommended to be adopted by Governments participating in tbe Regional Seas Programme. The methods and guidelines are prepared in co-operation with the relevant specialized bodies of the United Nations system as well as other organizations and are tested by a number of experts competent in the field relevant to the methods described. -
Coulomb Pairing Resonances in Multiple-Ring Aromatic Molecules
Coulomb pairing resonances in multiple-ring aromatic molecules D.L. Huber* Physics Department, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA Abstract We present an analysis of pairing resonances observed in photo-double-ionization studies of CnHm aromatic molecules with multiple benzene-like rings. The analysis, which is based on the Coulomb pairing model, is applied to naphthalene, anthracene, phenanthrene, pyrene and coronene, all of which have six-member rings, and azulene which is comprised of a five-member and a seven-member ring. There is a high energy resonance at ~ 40 eV that is found in all of the molecules cited and is associated with paired electrons localized on carbon sites on the perimeter of the molecule, each of which having two carbon sites as nearest neighbors. The low energy resonance at 10 eV, which is found only in pyrene and coronene, is attributed to the formation of paired HOMO electrons localized on arrays of interior carbon atoms that have the point symmetry of the molecule with each carbon atom having three nearest neighbors. The origin of the anomalous increase in the doubly charged to singly charged parent-ion ratio that is found above the 40 eV resonance in all of the cited molecules except coronene is discussed. *Mailing address: Physics Department, University of Wisconsin-Madison, 1150 University Ave., Madison, WI 53711, USA; e-mail: [email protected] 1 1. Introduction Recent studies of photo-double-ionization in CnHm multiple-ring (polycylic) aromatic molecules have revealed the existence of anomalous resonances in the ratio of the cross sections of doubly charged parent ions to singly charged parent ions I(2+)/I(1+) [1-4]. -
Construction of Novel Molecular Architectures from Anthracene Units and Acetylene Linkers*
Pure Appl. Chem., Vol. 84, No. 4, pp. 917–929, 2012. http://dx.doi.org/10.1351/PAC-CON-11-09-07 © 2012 IUPAC, Publication date (Web): 9 February 2012 Construction of novel molecular architectures from anthracene units and acetylene linkers* Shinji Toyota‡ Department of Chemistry, Faculty of Science, Okayama University of Science, 1-1 Ridaicho, Kita-ku, Okayama 700-0005, Japan Abstract: To create novel π-conjugated compounds, we constructed various molecular archi- tectures from anthracene units and acetylene linkers. Several cyclic oligomers ranging from dimers to dodecamers were synthesized by macrocyclization of acyclic precursors with metal-catalyzed coupling reactions. The structures, dynamic behavior, and spectroscopic fea- tures were greatly influenced by the number of anthracene units and the combination of building units and linkers. Optically active and circular dichroism (CD)-active enantiomers of some chiral cyclic oligomers were resolved by chiral high-performance liquid chromato - graphy (HPLC). Conformational analysis of hexamers and higher oligomers was performed with the aid of density functional theory (DFT) calculations. Acyclic oligomers underwent reversible folding–unfolding processes via photochemical and thermal reactions. These results suggest that transannular π–π interactions between anthracene units are important fac- tors in controlling the structural and spectroscopic properties and functions of π-conjugated compounds. The scope and perspectives of this molecular design are discussed on the basis of previous studies. Keywords: aromatic compounds; alkynes; π–π interactions; stereochemistry; structure. INTRODUCTION In the chemistry of aromatic compounds, oligomeric structures consisting of simple repeating units are fascinating motifs for the creation of new compounds. The merits of this molecular design are the acces- sibility to a large number of compounds from simple building units as well as the ease of tuning elec- tronic properties by structural modifications.