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dc.contributor.authorHou, B.
dc.contributor.authorYi, P.
dc.contributor.authorWang, Z.
dc.contributor.authorZhang, S.
dc.contributor.authorZhao, J.
dc.contributor.authorMancera, Ricardo
dc.contributor.authorCheng, Y.
dc.contributor.authorZuo, Z.
dc.date.accessioned2017-01-30T15:20:43Z
dc.date.available2017-01-30T15:20:43Z
dc.date.created2015-01-21T20:00:40Z
dc.date.issued2014
dc.identifier.citationHou, 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.
dc.identifier.urihttp://hdl.handle.net/20.500.11937/45418
dc.identifier.doi10.1016/j.comptc.2014.07.012
dc.description.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.

dc.publisherElsevier BV
dc.subjectGlobal Aromaticity
dc.subjects Aromaticity
dc.subjectp Aromaticity
dc.subjectELF
dc.subjectHeterobenzenes
dc.subjectNICS
dc.titleAssignment of aromaticity of the classic heterobenzenes by three aromatic criteria
dc.typeJournal Article
dcterms.source.volume1046
dcterms.source.startPage20
dcterms.source.endPage24
dcterms.source.issn2210-2728
dcterms.source.titleComputational and Theoretical Chemistry
curtin.note

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

curtin.departmentSchool of Biomedical Sciences
curtin.accessStatusOpen access


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