Interaction of two functional groups through the benzene ring: Theory and experiment

0333135 - ÚOCHB 2010 RIV US eng J - Journal Article
Böhm, S. - Exner, Otto
Interaction of two functional groups through the benzene ring: Theory and experiment.
Journal of Computational Chemistry. Roč. 30, č. 7 (2009), s. 1069-1074. ISSN 0192-8651. E-ISSN 1096-987X
Institutional research plan: CEZ:AV0Z40550506
Keywords : B3LYP * benzene derivatives * enthalpy of formation * resonance
Subject RIV: CF - Physical ; Theoretical Chemistry
Impact factor: 3.769, year: 2009

Energies of 132 benzene para bis-derivatives calculated within the framework of the density functional theory at the level B3LYP/6-311+G(d,p)//B3LYP/6-311+G(d,p) were used for correlations of two types. Correlation with the experimental enthalpies of formation clearly revealed that the published experimental data are generally not dependable and may be loaded with errors of more than 10 kJ mol-1. On the other hand, the calculated relative energies are biased so that the interaction of the two substituents is systematically overestimated. This shortcoming was insignificant for our correlations of the second type, in which the interaction of substituents expressed in terms of isodesmic reactions was analyzed depending on the effects of inductive and resonance.
Permanent Link: http://hdl.handle.net/11104/0178200