Infrared C-D Stretching and 2H NMR Spectra of Isopropyl-2-d 1-(p-Substituted Phenyl)ethyl Ketons. Evidence for the Hydrogen Bond-Like Interaction between C-D Group and Aromatic ?-Electrons

Article abstract of DOI:10.1246/bcsj.59.3529

Isopropyl-2-d 1-(p-X-phenyl)ethyl ketones (where, X=H, NO2, Br, Cl, C2H5, CH3, and NH2) were shown to have two absorption bands in the C-D sterching region.The absorption band at the higher frequency (ca. 2177 cm^-1) is assigned to the C-D...? approached conformer, and the high frequency shift is ascribed to the effect of steric compression.Weak C-D...? hydrogen bond was shown to occur by the measurement of the substituent effect on the formation constant and the relative enthalpy of the C-D...? approached conformer