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Aromaticity in heterocyclic analogues of benzene: Dissected NICS and current density analysis
Author(s) -
BáezGrez R.,
RabanalLeón Walter A.,
AlvarezThon Luis,
Ruiz Lina,
Tiznado W.,
PinoRios R.
Publication year - 2019
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3823
Subject(s) - aromaticity , chemistry , benzene , ring (chemistry) , pyridine , chemical shift , ring current , computational chemistry , molecule , isotropy , crystallography , organic chemistry , magnetic field , earth's magnetic field , physics , quantum mechanics
The magnetic aromaticity of 6‐membered monoheterocycles containing Group 13 to 16 elements (C 5 H 5 X, where X = SiH, GeH, N, P, As, O + , S + , Se + ) was assessed by using 2 magnetic descriptors: the π ‐electron contribution to the out‐of‐plane component of the nucleus‐independent chemical shifts (NICSzz, π ) and ring current strength. The results show that both descriptors lead to the same conclusion regarding magnetic aromaticity. However, they do not agree with the predictions obtained by isotropic NICS, which is a most commonly used method. Ring current strength and NICS π predict that benzene is the most aromatic molecule of the series, with an only slightly less aromatic pyridine. Additionally, aromaticity decreases when going down in the same group of the periodic system. The only exception is the pyrylium cation, which is predicted as the least aromatic species of this series.