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

• Type: Article in International Scientific Journal
• Date: 2013

Authors

Matos, MJ (Author) Other; Uriarte, E (Author) Other; Santana, L (Author) Other; Vilar, S (Author) Other

Journal

Title: Journal of Molecular Structure

Vol. 1041

Pages: 144-150

ISSN: 0022-2860

Publisher: Elsevier

Indexing

Scopus - 3 Citations

Other information

Authenticus ID: 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.

Language: English

Type (Professor's evaluation): Scientific