Purification and Properties of Ten Organic Sulfur Compounds-Second Series.

Haines, William E.; Helm, R. V.; Cook, G.L.; Ball, J.S.

doi:10.1021/j150539a009

Cited by 52 publications

(14 citation statements)

References 2 publications

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“… a Ref 151. b Ref 152. c Ref 153. d Ref 154. e Ref 155. f Ref 156. g Ref 157. h Ref 158. i Ref 159. j Ref 160. k Ref 161. l Ref 162. m Ref 163. n Ref 164. o Ref 165. p Ref 166. q Ref 167. r Ref 168. s Ref 169. t Ref 170. u Ref 171. v Ref 172. w Ref 173. x Ref 174. y Ref 175. z Ref 176. aa Ref 177. bb Ref 178. cc Ref 179. …”

Section: Figurementioning

confidence: 99%

Polarizable Atomic Multipole-Based Molecular Mechanics for Organic Molecules

Ren

Ponder

2011

J. Chem. Theory Comput.

437

690

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An empirical potential based on permanent atomic multipoles and atomic induced dipoles is reported for alkanes, alcohols, amines, sulfides, aldehydes, carboxylic acids, amides, aromatics and other small organic molecules. Permanent atomic multipole moments through quadrupole moments have been derived from gas phase ab initio molecular orbital calculations. The van der Waals parameters are obtained by fitting to gas phase homodimer QM energies and structures, as well as experimental densities and heats of vaporization of neat liquids. As a validation, the hydrogen bonding energies and structures of gas phase heterodimers with water are evaluated using the resulting potential. For 32 homo- and heterodimers, the association energy agrees with ab initio results to within 0.4 kcal/mol. The RMS deviation of hydrogen bond distance from QM optimized geometry is less than 0.06 Å. In addition, liquid self-diffusion and static dielectric constants computed from molecular dynamics simulation are consistent with experimental values. The force field is also used to compute the solvation free energy of 27 compounds not included in the parameterization process, with a RMS error of 0.69 kcal/mol. The results obtained in this study suggest the AMOEBA force field performs well across different environments and phases. The key algorithms involved in the electrostatic model and a protocol for developing parameters are detailed to facilitate extension to additional molecular systems.

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Section: Figurementioning

confidence: 99%

Polarizable Atomic Multipole-Based Molecular Mechanics for Organic Molecules

Ren

Ponder

2011

J. Chem. Theory Comput.

437

690

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“…Densities for 2,3-benzothiophene were measured by Haines et al (44)and Auwers, (45) and estimated by Gray(46) with Tb and the molecular mass, Also, the liquid-phase density was measured in this research with the volume and mass of sample used in the adiabatic heat-capacity calorimetry studies. The measured value was 1120t:30kg.m "3 at 332 K.…”

Section: Comparison Withliterature Densitiesmentioning

confidence: 92%

The thermodynamic properties of 2,3-benzothiophene

Chirico¹,

Knipmeyer²,

Nguyen³

et al. 1991

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Upgrading of heavy fossil fuels is normally done by hydrotreating in the presence of catalysts, such as sulfided CoO-MoO3/7-AI203, at 5 to 15 MPa pressure of hydrogen and 575 to 700 K. The efficient use of expensive hydrogen in this process is essential to the economic viability of alternative fuel sources (heavy petroleum, tar sands, shale oil, and the products of the liquefaction of coal). 2,3-Benzothiophene is widely used as a model compound in catalyst-comparison j, and kinetics studies of the hydrodesulfurization (HDS) mechanism. To perform a thermodynamic analysis of the 2,3-benzothiophene/hydrogen reaction network at the process temperatures, Gibbs energies of reaction at those high temperatures are required for the molecules involved. At present, the thermodynamic information necessary for the analysis of possible reaction pathways and stable intermediates is not available. Only crude estimates based on the thermodynamicproperties of thiophene are available. The studies reported here begin to provide the required information. A second application of the results reported ilere is in the area of property estimations. Because of the enormous number of individual compounds present in fossil materials, group-contribution and corresponding-states methods are employed to estimate thermodynamic properties in the absence of measured values. Much of the empirical information necessary to extend existing group-contribution parameterizations to include polycyclic aromatic sulfur-containing species does not exist. The studies reported here provide the basis for the accurate estimation of many physical properties for this class of molecules over a broad temp_=,aturerange.

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“…However, the photooxidation of BT itself may have been studied unwittingly a long time ago. 37,62 Haines et al noted that benzo[b]thiophene 58d changes when kept for 6 months or longer in daylight. The authors reported that benzo[b]naphtho [1,2-d]thiophene 64 is formed within that time (Fig.…”

Section: Photochemistry Of Benzo[b]thiophene S-oxides and Benzo[b]thiophene Ss-dioxidesmentioning

confidence: 99%

Photochemical and Electrochemical Oxygenation of Thiophenes, Benzo[b]Thiophenes and Dibenzothiophenes; Photochemical and Electrochemical Behaviour of Their Oxygenated Intermediates and Products

Thiemann

2010

Journal of Chemical Research

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Prof. Dr. Thies Thiemann received his chemical education at the universities of Hamburg and Tuebingen, Germany. After obtaining a PhD degree in organic chemistry at the University of Hamburg, he moved to Japan for his postdoctorate at Kyushu University, Fukuoka. Thies has also worked at joined the chemistry faculty of the United Arab Emirates University in Al Ain, Abu Dhabi. His main focus is on organic synthetic chemistry, especially in the areas of steroidal and heterocyclic chemistry. He is author/co-author of over 150 papers, nine reviews, three book chapters and five patents. S-oxides and benzo[b]thiopheneS,S-dioxides 672 6. Photochemistry of thiophene S-oxides 675 7. Electrochemical oxidation and reduction of thiophenes, thiophene S-oxides and related compounds 675 8. Conclusions 676 9. References 678The photooxygenation of thiophenes, benzo[b]thiophenes and dibenzothiophenes is discussed, especially in view of the oxidative removal of these S-containing contaminants from fuels. Furthermore, the photochemistry of the intermediates and the products from these processes is detailed. Finally, an account is given of the electrooxidation of thiophenes and derivatives to the corresponding sulfoxides and sulfones as well as of the electrochemical behaviour of the intermediate thiophene S-oxides.

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Purification and Properties of Ten Organic Sulfur Compounds-Second Series.

Cited by 52 publications

References 2 publications

Polarizable Atomic Multipole-Based Molecular Mechanics for Organic Molecules

Polarizable Atomic Multipole-Based Molecular Mechanics for Organic Molecules

The thermodynamic properties of 2,3-benzothiophene

Photochemical and Electrochemical Oxygenation of Thiophenes, Benzo[b]Thiophenes and Dibenzothiophenes; Photochemical and Electrochemical Behaviour of Their Oxygenated Intermediates and Products

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