South African Journal of Chemistry
versión On-line ISSN 1996-840X
SHEIKHI, Masoome; SHEIKH, Davood y RAMAZANI, Ali. Three-component Synthesis of Electron-poor Alkenes using Isatin Derivatives, Acetylenic Esters, Triphenylphosphine and Theoretical Study. S.Afr.j.chem. (Online) [online]. 2014, vol.67, pp. 0-0. ISSN 1996-840X.
Synthesis of electron-poor alkenes has been reported by 1,2-proton shift and elimination of triphenyl phosphine from phosphorus ylide in good to high yields. The structures of six novel products were deduced from their IR, 1H NMR, and 13C NMR spectra. The B3LYP/HF calculations for computation of 1H and 13C NMR chemical shifts have been carried out for the compounds with the 6-31G* basis set utilizing the GIAO approach. In addition, theoretical configurations of the title compound were studied in terms of the combined analysis of the HOMO-LUMO energy gap, NBO analysis, thermodynamic parameters and molecular electrostatic potential (MEP). Also ionization potential (I), electron affinity (A), chemical hardness (η), electronic chemical potential (μ) and electrophilicity (ω) of the title molecule are reported. All calculations were performed using B3LYP method with the 6-31G* basis set.
Palabras clave : Isatin; electron-poor alkenes; DFT; NBO; HOMO; LUMO.