HYDROGEN-BONDED COMPLEXES OF 1-CHLORO-2-METHYLPROPAN-2-OL WITH KETONES

The interaction of 1-chloro-2-methylpropan-2-ol (CMP) with acetone and methyl ethyl ketone was examined in dilute carbon tetrachloride solut ion. The strengths of the hydrogen-bonded complexes were compared with those of the corresponding complexes of trimethyl carbinol and 1,1,1- trichloro-2-methyl-propan-2-ol with ketones. The aim was to explain th e inductive effect of the chlorine atom on the strength of carbinol-ke tone hydrogen-bonded complexes, The monomer IR band of CPM appears in solution as a composite of five sub-bands, signifying that many confor mers are present; this was confirmed by quantum chemical calculations. Chlorine substitution increases the strength of the hydrogen bond. (C ) 1997 Elsevier Science B.V.