Effect of water and deuterated water on Raman spectra of chloroacetone: evidence for the conformational effect on hydration

The gauche–syn isomerization of chloroacetone in water has been studied using Raman spectroscopy as a model for the effects of hydration on molecular conformation. The spectra in water and deuterate water indicate the formation of a new type of hydrogen bonding between the chlorine atom and water only in the syn conformer. A close contact between the chlorine and oxygen atoms in the syn form facilitates the chlorine atom forming this hydrogen bond.