Polarities and hydrogen-bonding abilities of the aromatic derivatives of cyclohex-2-enone

Abstract

The relative basicities of 3-aryl-5-phenylcyclohex-2-en ones have been determined by i.r. spectroscopy from the shifts of the stretching frequency of the hydroxy-group of phenol hydrogen-bonded with these ketones and from the ν_co values (in KBr, CCl₄, and CHCl₃) together with the dipole moments (in benzene). The values are discussed and ccmpared with those of arylideneacetones having analogous conjugated systems. It is shown that the fixed s-trans-configuration of cyclohexenone derivatives causes their high polarities and basicities. Correlation analysis has been performed and it is found that the rigid π-system of cyclohexenone possesses a substantially better transmission of electronic influence in comparison with carbonyl compounds with an open-chain structure.