PMID: 11312942Apr 21, 2001Paper

The influence of substituent groups on the resonance stabilization of benzene. An ab initio computational study

The Journal of Organic Chemistry
Donald W Rogers, Frank J. McLafferty

Abstract

Accurate G3(MP2) calculations of the enthalpies of formation (Delta(f)H298) of organic molecules permit replication and extension of calculations that were formerly dependent on experimental thermochemical results. A case in point is Kistiakowski's classical calculation of the total stabilization enthalpy of benzene relative to that of cyclohexene, called for many years the "resonance energy". This paper investigates extension of the classical calculation to substituted benzenes. Slight modification of the usual procedure for Delta(f)H298 determination permits exclusion of all empirical information, leaving a purely ab initio result. Stabilization enthalpies relative to the corresponding 4-substituted cyclohexenes are presented for benzene, toluene, aniline, phenol, phenylacetylene, styrene, ethylbenzene, and phenylhydrazine. In the process of calculating these stabilization enthalpies, we have also obtained 42 values of Delta(f)H298 for monosubstituted benzenes, cyclohexenes, and cyclohexanes, 24 of which are not in the standard reference literature. For the remaining 18 G3(MP2) results, the unsigned mean difference between calculated Delta(f)H298 values and experimental results is +/-0.91 kcal x mol(-1).

Citations

Nov 29, 2002·The Journals of Gerontology. Series A, Biological Sciences and Medical Sciences·Atsuyoshi ShimadaMasanori Hosokawa
Oct 21, 2015·The Journal of Physical Chemistry. a·Thomas C Allison, Donald R Burgess
Oct 9, 2004·The Journal of Organic Chemistry·Donald W RogersJoel F Liebman
Oct 25, 2001·Journal of the American Chemical Society·M D ChordiaW D Harman
Dec 8, 2005·The Journal of Physical Chemistry. a·Donald W RogersNikita Matsunaga

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