DFT studies on structure and spectroscopic properties of α,β-unsaturated ester dipolarophiles; Application in prediction of their reactivities with C-phenyl-N-methyl nitrone

Centre of Advanced Studies on Natural Products including Synthesis, Department of Chemistry, University College of Science and Technology, Kolkata-700 009, India

E-mail : ablabcu@yahoo.co.uk; banerjijulie@yahoo.com

Manuscript received 06 September 2015, accepted 06 January 2016

The optimized geometries, electrostatic potential maps, FMO energies, electronic chemical potentials, chemi­cal hardness, chemical softness, global and local electrophilicity indices and Fukui indices of a number of α,β-unsatur­ated esters have been calculated at DFT/B3LYP/6-31++G(d,p) level of theory. DFT/B3LYP/6-311++G(d,p) calculated ¹H NMR and experimentally recorded chemical shift values show good agreement. The fundamental vibrational modes have been assigned by comparing the theoretically computed and experimental frequencies. The thermodynamic param­eters are also presented. The calculated reactivity indices have been used to predict regioselectivities of these unsatur­ated esters as dipolarophiles with C-phenyl-N-methyl nitrone.