Comparative study of the 3-phenylcoumarin scaffold: Synthesis, X-ray structural analysis and semiempirical calculations of a selected series of compounds

作者：Matos Maria J^*; Vilar Santiago; Tatonetti Nicholas P; Santana Lourdes; Uriarte Eugenio

来源：Journal of Molecular Structure, 2013, 1050: 185-191.

DOI：10.1016/j.molstruc.2013.07.037

• Coumarin derivatives
• Synthesis
• X-ray structural analysis
• Conformational analysis
• Semiempirical calculations

Compounds 1 (6-methyl-3-phenylcoumarin), 2 (3-(o-methoxyphenyl)-6-methylcoumarin) and 3 (3-(m-methoxyphenyl)-6-methylcoumarin) were synthesized by a Perkin reaction between the 2-hydroxy-5methylbenzaldehyde and the corresponding phenyl acetic acid. H-1 and C-13 NMR and X-ray diffractometry determined the molecular structures of the derivatives. A comparative study between compounds 1, 2 and 3, based on the structural results, was carried out. In addition, the X-ray structures were compared to those obtained combining conformational analysis with semiempirical methodologies (AM1 and PM3). The results provided by the semiempirical calculations in gas phase are in strong agreement with the Xray method for the three molecules under study, meaning that the determination of the 3D structure for this type of compounds could be extrapolated from semiempirical studies.

• 出版日期2013-10-24