Assignment of aromaticity of the classic heterobenzenes by three aromatic criteria
MetadataShow full item record
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.
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
Showing items related by title, author, creator and subject.
Molecular modeling of Bt Cry1Ac (DI-DII)-ASAL (Allium sativum lectin)-fusion protein and its interaction with aminopeptidase N (APN) receptor of Manduca sextaTajne, S.; Sanam, R.; Gundla, R.; Gandhi, Neha; Mancera, Ricardo; Boddupally, D.; Vudem, D.; Khareedu, V. (2012)Genetic engineering of Bacillus thuringiensis (Bt) Cry proteins has resulted in the synthesis of various novel toxin proteins with enhanced insecticidal activity and specificity towards different insect pests. In this ...
Warton, Benjamin (1999)This thesis reports the results of investigations carried out into the composition of the saturate and aromatic unresolved complex mixtures (UCMs) in crude oils. It is divided into two sections. Section A reports on studies ...
Thermally assisted hydrolysis and derivatisation techniques for the characterisation of organic materialsChallinor, John M. (1998)This thesis describes the development of a novel method for the rapid identification of complex organic materials, including macromolecules, that involves a high temperature simultaneous hydrolysis and derivatisation ...