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Group additive modeling of substituent effects in monocyclic aromatic hydrocarbon radicals

Alper Ince, Hans-Heinrich Carstensen UGent, Maarten Sabbe UGent, Marie-Françoise Reyniers UGent and Guy Marin UGent (2017) AICHE JOURNAL. 63(6). p.2089-2106
abstract
The thermodynamic properties of the unsubstituted and substituted phenyl, phenoxy, anisyl, benzoyl, styryl and benzyl radicals with six substituents (hydroxy, methoxy, formyl, vinyl, methyl, and ethyl) are calculated with the bond additivity corrected (BAC) post-Hartree-Fock G4 method. Bond dissociation energies of monocyclic aromatic hydrocarbons are calculated and used to identify substituent interactions in these radicals. Benson's Group Additivity (GA) scheme is extended to aromatic radicals by defining 6 GAV and 29 NNI parameters through least squares regression to a database of thermodynamic properties of 369 radicals. Comparison between G4/BAC and GA calculated thermodynamic values shows that the standard enthalpies of formation generally agree within 4 kJ mol−1, whereas the entropies and the heat capacities deviate less than 4 J mol−1 K−1.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
thermochemistry, substituted monocyclic aromatic radicals, bond dissociation energies, group additivity, lignin pyrolysis
journal title
AICHE JOURNAL
AlChE J.
volume
63
issue
6
pages
2089 - 2106
publisher
Wiley-Blackwell
Web of Science type
Article
Web of Science id
000400658400025
ISSN
0001-1541
DOI
10.1002/aic.15588
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
8525511
handle
http://hdl.handle.net/1854/LU-8525511
date created
2017-06-28 12:27:56
date last changed
2017-06-29 08:49:01
@article{8525511,
  abstract     = {The thermodynamic properties of the unsubstituted and substituted phenyl, phenoxy, anisyl, benzoyl, styryl and benzyl radicals with six substituents (hydroxy, methoxy, formyl, vinyl, methyl, and ethyl) are calculated with the bond additivity corrected (BAC) post-Hartree-Fock G4 method. Bond dissociation energies of monocyclic aromatic hydrocarbons are calculated and used to identify substituent interactions in these radicals. Benson's Group Additivity (GA) scheme is extended to aromatic radicals by defining 6 GAV and 29 NNI parameters through least squares regression to a database of thermodynamic properties of 369 radicals. Comparison between G4/BAC and GA calculated thermodynamic values shows that the standard enthalpies of formation generally agree within 4 kJ mol\ensuremath{-}1, whereas the entropies and the heat capacities deviate less than 4 J mol\ensuremath{-}1 K\ensuremath{-}1. },
  author       = {Ince, Alper and Carstensen, Hans-Heinrich and Sabbe, Maarten and Reyniers, Marie-Fran\c{c}oise and Marin, Guy},
  issn         = {0001-1541},
  journal      = {AICHE JOURNAL},
  keyword      = {thermochemistry,substituted monocyclic aromatic radicals,bond dissociation energies,group additivity,lignin pyrolysis},
  language     = {eng},
  number       = {6},
  pages        = {2089--2106},
  publisher    = {Wiley-Blackwell},
  title        = {Group additive modeling of substituent effects in monocyclic aromatic hydrocarbon radicals},
  url          = {http://dx.doi.org/10.1002/aic.15588},
  volume       = {63},
  year         = {2017},
}

Chicago
Ince, Alper, Hans-Heinrich Carstensen, Maarten Sabbe, Marie-Françoise Reyniers, and Guy Marin. 2017. “Group Additive Modeling of Substituent Effects in Monocyclic Aromatic Hydrocarbon Radicals.” Aiche Journal 63 (6): 2089–2106.
APA
Ince, A., Carstensen, H.-H., Sabbe, M., Reyniers, M.-F., & Marin, G. (2017). Group additive modeling of substituent effects in monocyclic aromatic hydrocarbon radicals. AICHE JOURNAL, 63(6), 2089–2106.
Vancouver
1.
Ince A, Carstensen H-H, Sabbe M, Reyniers M-F, Marin G. Group additive modeling of substituent effects in monocyclic aromatic hydrocarbon radicals. AICHE JOURNAL. Wiley-Blackwell; 2017;63(6):2089–106.
MLA
Ince, Alper, Hans-Heinrich Carstensen, Maarten Sabbe, et al. “Group Additive Modeling of Substituent Effects in Monocyclic Aromatic Hydrocarbon Radicals.” AICHE JOURNAL 63.6 (2017): 2089–2106. Print.