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Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria

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Authors
Hou, B.
Yi, P.
Wang, Z.
Zhang, S.
Zhao, J.
Mancera, Ricardo
Cheng, Y.
Zuo, Z.
Date
2014
Type
Journal Article

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Hou, B. and Yi, P. and Zhang, S. and Zhao, J. and Mancera, R. and Cheng, Y. and Zuo, Z. 2014. Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria. Computational and Theoretical Chemistry. 1046: pp. 20-24.
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Computational and Theoretical Chemistry
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School of Biomedical Sciences
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NOTICE: this is the author’s version of a work that was accepted for publication in Computational and Theoretical Chemistry. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Computational and Theoretical Chemistry, Vol. 1046 (2014). DOI: 10.1016/j.comptc.2014.07.012

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Abstract

Aromaticity is a key concept in physical organic chemistry. The aromatic order of the classic heterobenzenes was reported in experiment early. However, the unambiguous criteria used to validate the aromaticity of that were controversial or inadequate in theory. In this work, the global aromaticity of the compounds has been studied using the ELF, NICS and ISE. NICS(max)zz was calculated based on the maximum NICS contribution to the out-of-plane zz tensor component. Two types of bonds are observed. The correlations between NICS(max)σzz and NICS(max)πzz with respect to aromaticity are demonstrated, specifically between NICS(max)πzz and ELFπ (cc = 0.98) for π bonds. For σ bonds, the different electron delocalization of σ bonds out of the plane of the ring predicted well the discrepancies between NICS(max)σzz and ELFσ. The σ aromatic order of the classic heterobenzenes (C5H5N > C6H6 > C5H5P > C5H5As > C5H5Bi, C5H5Sb) was proved via the level of electronic delocalization.