Electronic Structure and Stability of Benzotriazoles

Autor:	Tareq Abu-Izneid, Leo Klasinc, Igor Novak, Branka Kovač
Rok vydání:	2009
Předmět:	chemistry.chemical_compound Isodesmic reaction chemistry Computational chemistry Nitration Triazole Ab initio Substituent Regioselectivity Electronic structure Physical and Theoretical Chemistry photoelectron spectra benzotriazoles DFT OVGF Tautomer
Zdroj:	The Journal of Physical Chemistry A. 113:9751-9756
ISSN:	1520-5215 1089-5639
DOI:	10.1021/jp905640b
Popis:	The electronic structures and relative stabilities of N-substituted benzotriazoles (BtR) have been studied by UV photoelectron spectroscopy (UPS) and high-level ab initio methods. We show that the UPS spectrum of 1H-benzotriazole corresponds to a mixture of tautomers. The N-substituent effects in benzotriazoles were shown to depend on the mode of attachment of the substituent to the Bt residue. We have estimated the conjugation effects between benzene and triazole rings in N-substituted benzotriazoles by using isodesmic reactions and high-level composite ab initio methods. The 2H-benzotriazoles (Bt2R) appear to be stabilized upon ring conjugation while on the other hand the 1H-benzotriazoles (Bt1R) are destabilized. The electronic structure of benzotriazoles can be related to photocycloaddition reactions and to regioselectivity exhibited during nitration.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b605a3dc6f3c37fa35c9eab0f0d6cab2 https://doi.org/10.1021/jp905640b Zobrazit plný text záznamu