Aromaticity in heterocyclic analogues of benzene: Dissected NICS and current density analysis

R. Báez-Grez, Walter A. Rabanal-León, Luis Alvarez-Thon, Lina Ruiz, W. Tiznado, R. Pino-Rios

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The magnetic aromaticity of 6-membered monoheterocycles containing Group 13 to 16 elements (C5H5X, 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 NICSπ 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.

Original languageEnglish
Article numbere3823
JournalJournal of Physical Organic Chemistry
Volume32
Issue number1
DOIs
Publication statusAccepted/In press - 1 Jan 2018

Keywords

  • Benzene analogues
  • Current density
  • Magnetic aromaticity
  • NICS

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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