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

•Compound 1 (4-Methyl-N-(coumarin-3-yl)benzamide) was synthesized.•Compound 2 (coumarin-3-yl)-4-methylbenzoate was synthesized.•1H and 13C NMR and X-ray diffractometry determined the molecular structures.•Semiempirical calculations presented an alternative to determine the 3D structures.•AM1 and PM3 yielded results reproducing the whole 3D structure of both molecules.

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.

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