کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1408858 | 1501773 | 2013 | 7 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Synthesis, NMR characterization, X-ray structural analysis and theoretical calculations of amide and ester derivatives of the coumarin scaffold Synthesis, NMR characterization, X-ray structural analysis and theoretical calculations of amide and ester derivatives of the coumarin scaffold](/preview/png/1408858.png)
• 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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Journal: Journal of Molecular Structure - Volume 1041, 10 June 2013, Pages 144–150