A computational study of the structure, aromaticity and enthalpy of formation of UVA filter 4-tert-butyl-4 '-methoxydibenzoylmethane

• Tipo: Artigo em Revista Científica Internacional
• Data: 2014

Autores

Paulo J O Ferreira (Autor) Outra; Luis Pinto da Silva (Autor) Outra; Dario J R Duarte (Autor) Outra; Margarida S Miranda (Autor) Outra; Joaquim C G E Esteves da Silva (Autor) FCUP

Revista

Título: Computational and Theoretical Chemistry

Vol. 1038

Páginas: 6-16

ISSN: 2210-271X

Editora: Elsevier

Indexação

ISI Web of Knowledge - 1 Citação

Scopus - 2 Citações

Classificação Científica

FOS: Ciências exactas e naturais > Química

Outras Informações

ID Authenticus: P-009-S9B

DOI: 10.1016/j.comptc.2014.03.037

Abstract (EN): In this study we have performed a density functional theory (DFT) study of the molecular structure and energetics of the enol and keto tautomers of UVA filter 4-tert-butyl-4'-methoxydibenzoylmethane (BMDBM) and for comparison and validation purposes a similar study has been carried out for the parent molecule: dibenzoylmethane (DBM). The molecular structure of the enol and keto tautomers were obtained at the B3LYP/6-311++G(d,p) level. The enol forms were found to have a strong intramolecular resonance assisted hydrogen bond that accounts for the greater energetic stability of the enol relative to the keto form. The aromatic character of the six-membered enol rings has been analyzed by calculation of Nucleus Independent Chemical Shifts (NICS). The standard molar enthalpy of formation in the gas phase of BMDBM was derived from appropriately chosen reactions.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 11