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Double Group Transfer Reactions as Indicators of Aromatic Stabilization
Author(s) -
Frenking Gernot,
Cossío Fernando P.,
Sierra Miguel A.,
Fernández Israel
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700547
Subject(s) - chemistry , aromaticity , ring (chemistry) , hydrogen atom , molecule , computational chemistry , character (mathematics) , group (periodic table) , decomposition , density functional theory , functional group , transition state , organic chemistry , catalysis , geometry , mathematics , polymer
The main features of double hydrogen atom transfer reactions in syn ‐sesquinorbornanes, which involve the concomitant formation of an aromatic ring, have been studied computationally within the framework of Density Functional Theory. The very good linear correlations, which exhibit high correlation coefficients between the recently available Aromatic Stabilization Energies (ASE) from the Energy Decomposition Analysis (EDA) method and the activation and reaction energies, as well as geometric features (C–C bond lengths) of the corresponding transition states of the transformations, suggest that the calculated values are useful in estimating the aromatic character of a molecule. The studied process may be used for benchmarking of energetic aromatic indices. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)