Synthesis, NMR characterization, X-ray structural analysis and theoretical calculations of amide and ester derivatives of the coumarin scaffold

• Tipo: Artigo em Revista Científica Internacional
• Data: 2013

Autores

Matos, MJ (Autor) Outra; Uriarte, E (Autor) Outra; Santana, L (Autor) Outra; Vilar, S (Autor) Outra

Revista

Título: Journal of Molecular Structure

Vol. 1041

Páginas: 144-150

ISSN: 0022-2860

Editora: Elsevier

Indexação

Scopus - 3 Citações

Outras Informações

ID Authenticus: P-00R-0N1

DOI: 10.1016/j.molstruc.2013.03.014

Abstract (EN): Compounds 1 (4-methyl-N-(coumarin-3-yl)benzamide) and 2 ((coumarin-3-yl)-4-methylbenzoate) were synthesized by linking the coumarin system (3-aminocoumarin or 3-hydroxycoumarin, respectively) to a p-toluoylchloride. 1H and 13C NMR and X-ray diffractometry determined the molecular structures of both derivatives. The X-ray results were compared to those obtained by conformational analysis followed by semiempirical methodologies (AM1 and PM3). The theoretical calculations yielded results reproducing the whole three-dimensional (3D) structure of both molecules in a good agreement with X-ray structural analysis. The global structures of the two compounds are very similar in the two studied environments, meaning that the structural determination in the gas phase can be extrapolated. A comparative study between compounds 1 and 2, based on the structural results, was carried out.

Idioma: Inglês

Tipo (Avaliação Docente): Científica