Study of Electron Delocalization in 1,2-, 1,3-, and 1,4-Azaborines Based on the Canonical Molecular Orbital Contributions to the Induced Magnetic Field and Polyelectron Population Analysis

The Journal of Physical Chemistry. a
Anastasios G PapadopoulosMichael P Sigalas

Abstract

The electron delocalization in 1,2-azaborine, 1,3-azaborine, and 1,4-azaborine is studied using canonical molecular orbital contributions to the induced magnetic field (CMO-IMF) method and polyelectron population analysis (PEPA). Contour maps of the out-of-plane component of the induced magnetic field (Bz(ind)) of the π system show that the three azaborines, in contrast with borazine, sustain much of benzene's π-aromatic character. Among them, 1,3-azaborine exhibits the strongest π delocalization, while 1,4-azaborine is the weakest. Contour maps of Bz(ind) for individual π orbitals reveal that the differentiation of the magnetic response among the three isomers originates from the π-HOMO orbitals, whose magnetic response is governed by rotational allowed transitions to unoccupied orbitals. The low symmetry of azaborines enables a paratropic response from HOMO to unoccupied orbitals excitations, with their magnitude depending on the shape of interacting orbitals. 1,3-Azaborine presents negligible paratropic contributions to Bz(ind) from HOMO to unoccupied orbitals transitions, where 1,2- and 1,4-azaborine present substantial paratropic contributions, which lead to reduced diatropic response. Natural bond orbital (NBO) analysis e...Continue Reading

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Citations

May 31, 2016·Angewandte Chemie·Xuguang LiuShih-Yuan Liu
Aug 24, 2017·Journal of Computational Chemistry·Nickolas D CharistosMichael P Sigalas
Jun 30, 2019·Physical Chemistry Chemical Physics : PCCP·Paul A BrownKevin L Shuford
Jan 10, 2018·Journal of the American Chemical Society·Zachary X Giustra, Shih-Yuan Liu
Jan 12, 2021·The Journal of Physical Chemistry. a·Rabia AyubHenrik Ottosson

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