Intramolecular hydrogen bonds involving polar carbon–hydrogen bonds: infrared and 1H nuclear magnetic resonance spectra of some cyanomethyl and benzyl sulphones

Abstract

Two series of sulphones, containing respectively the cyanomethylsulphonyl and the benzylsulphonyl groups, have been prepared, in which a polar methylene group is allowed on steric grounds to interact intramolecularly with a nearby donor atom. The i.r. and ¹H n.m.r. spectra of these sulphones are compared with spectra of reference compounds in which no such interaction is possible. No conclusive evidence for intramolecular hydrogen bonds is found: possible causes for the observed spectral shifts are discussed.