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

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• 作者：Maria J. Matos ; ^{mariacmatos@gmail.com} ; Eugenio Uriarte ^{eugenio.uriarte@usc.es} ; Lourdes Santana ^{lourdes.santana@usc.es} ; Santiago Vilar ^{qosanti@yahoo.es}
• 关键词：Coumarin derivatives ; Synthesis ; X-ray structural analysis ; NMR analysis ; Conformational analysis ; Semiempirical calculations
• 刊名：Journal of Molecular Structure
• 出版年：2013
• 出版时间：10 June, 2013
• 年：2013
• 卷：1041
• 期：Complete
• 页码：144-150
• 全文大小：1140 K

文摘

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.