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A Theoretical Study of the Aromaticity in Neutral and Anionic Borole Compounds

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)

Royal Society of Chemistry (RSC)

Manager: Ministerio de Ciencia e Innovación (Espanya)
Generalitat de Catalunya. Agència de Gestió d’Ajuts Universitaris i de Recerca
Ministerio de Economía y Competitividad (Espanya)
Author: Jiménez Halla, José Óscar Carlos
Matito i Gras, Eduard
Solà i Puig, Miquel
Braunschweig, Holger
Hörl, Christian
Krummenacher, Ivo
Wahler, Johannes
Date: 2015
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)
Format: application/pdf
Document access: http://hdl.handle.net/10256/11155
Language: eng
Publisher: Royal Society of Chemistry (RSC)
Collection: info:eu-repo/semantics/altIdentifier/doi/10.1039/c4dt03445g
info:eu-repo/semantics/altIdentifier/issn/1477-9226
info:eu-repo/semantics/altIdentifier/eissn/1477-9234
info:eu-repo/grantAgreement/MICINN//CTQ2011-23156/ES/AVANCES EN CATALISIS Y AROMATICIDAD/
AGAUR/2009-2014/2009 SGR-637
AGAUR/2014-2016/2014 SGR-931
info:eu-repo/grantAgreement/MINECO//CTQ2013-41236-ERC/ES/UNA NUEVA ESTRATEGIA EN DFT: FUNCIONALES HIBRIDOS ADAPTADOS A LA CORRELACION ELECTRONICA/
info:eu-repo/grantAgreement/EC/FP7/294240/EU/Development of new non-empirical DFT functionals./NEWDFTFUNCT
Rights: Tots els drets reservats
Subject: Compostos heterocíclics
Heterocyclic compounds
Aromaticitat (Química)
Aromaticity (Chemistry)
Title: A Theoretical Study of the Aromaticity in Neutral and Anionic Borole Compounds
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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