A theoretical assignment of the stability of the isomerism in coumarin
کد مقاله : 1130-PHYSCHEM20
نویسندگان:
فرخنده بایستی زهی *، 1مهدی شهرکی، 2فاطمه قدسی
1استادیار/دانشگاه سیستان و بلوجستان
2دانشگاه سیستان وبلوچستان
چکیده مقاله:
The reaction between dialkyl acetylenedicarboxylates (DAADs) and trialkyl phosphites in the presence of 4-hydroxycoumarin lead to product 3-[2-(dialkoxyphosphoryl)-1, 2-dialkoxycarbonyl-ethyl]-4- hydroxycoumarins. Quantum mechanical calculations were undertaken for ascertain of stability of two isomers possible product 4. Herein, theoretical calculations have been employed for the assignment of the most stable isomers anti and gauche product 4 at both the HF/6-31G (d, p) level and the B3LYP method with 6-311++G (d, p) basis set. The results showed that product 4 with anti HCCH arrangements are more stable than 4 with gauche HCCH arrangements. The results (theoretical calculations) were consistent with the experimental data obtained from NMR spectroscopy.
کلیدواژه ها:
Stereoselectivity, 4-Hydroxycoumarin, Phosphonates, Isomerism, Computational methods
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