CONFORMATIONAL ANALYSIS OF 2-(DIPHENYLPHOSPHANYL)-N,N-DIMETHYL-1-BENZ AMIDE AND 2-(DIPHENYLPHOSPHANYL)-PHENYL-PYRROLIDIN-1-YL-METHANONE BY NMR SPECTROSCOPY

We have synthesized 2-(Diphenylphosphanyl)-N, N-dimethyl-1-benzamide (1) and 2-(Diphenylphosphanyl)- phenyl-pyrrolidin-1-yl-methanone (2), and examined their conformations on the basis of NMR spectral data. Conformational analysis of the compounds is useful in deducing the structure in which they are active as a catalyst. In the present NMR measurements, ¹H-X fg-JHMBC (field gradient J-Resolved Hetero-nuclear Multiple-Bond Correlation) spectroscopy was implemented as a tool for the determination of hetero-nuclear three bond, phosphorus and protons and carbon-protons coupling constants. By fitting a sine curve to the experimental data by the method of 3D J-resolved HMBC NMR measurements, accurate ⁿ J _HX coupling constants were obtained. From the coupling constants, the corresponding dihedral angles, H3-C2-C3-P, H12-C12-C11-P, H16-C16-C11-P, H18-C18-C17-P, and H22-C22-C17-P, of compounds (1) and (2) were determined. The optimized structures of the compounds were obtained by molecular orbital calculations in which the dihedral angles experimentally determined were used.