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A theoretical study of the aromaticity in neutral and anionic borole compounds.

Authors
  • Jimenez-Halla, J Oscar C1
  • Matito, Eduard
  • Solà, Miquel
  • Braunschweig, Holger
  • Hörl, Christian
  • Krummenacher, Ivo
  • Wahler, Johannes
  • 1 Department of Chemistry (DCNE), University of Guanajuato, Noria Alta s/n 36050 Guanajuato, Mexico. [email protected] , (Mexico)
Type
Published Article
Journal
Dalton Transactions
Publisher
The Royal Society of Chemistry
Publication Date
Apr 21, 2015
Volume
44
Issue
15
Pages
6740–6747
Identifiers
DOI: 10.1039/c4dt03445g
PMID: 25494445
Source
Medline
License
Unknown

Abstract

In this contribution, we have evaluated the (anti)aromatic character of thirty-four different borole compounds in their neutral and reduced states based on two aromaticity indices, namely nucleus-independent chemical shift (NICS) and multicenter indices (MCI), calculated at the PBE0/6-31+G(d,p) level of theory. Both indices corroborate the notion that neutral borole compounds are antiaromatic and become increasingly aromatic upon addition of electrons. Effects of the ring substituents on the degree of (anti)aromaticity are discussed together with differences in the two theoretical methods, which are on the one hand based on magnetic (NICS) and on the other hand based on electronic criteria (MCI).

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