First Experimental Evidence of an Intramolecular H Bond between Aliphatic Cl and Aromatic C–H

Abstract

The first example of an intramolecular H bond between aliphatic Cl and aromatic C–H was observed in the crystal of <i>C</i>₂-symmetric (4<i>R</i>,5<i>R</i>)-4,5-bis(diphenylchloromethyl)-1,3,2-dioxathiolane 2-oxide. In this case one Cl atom is engaged in H-bonding with two <i>ortho</i>-C–H groups in the axial and equatorial phenyl planes, with the recorded distances of 2.562 Ǻ and 2.804 Ǻ, respectively. The observed angle for C_<i>a</i>–H–Cl is 108.41° and that for C_<i>q</i>–H–Cl is 96.53°