Conformational analysis of 2-chloro-2-fluoroacetaldehyde and calculated transition state structures of nucleophilic addition reactions.

The rotational profiles and conformational minima of 2-chloro-2-fluoroacetaldehyde have been calculated using ab initio methods at the MP2/6-31G(d)//HF/6-31G(d) level of theory. Two minima could be located on the potential energy hypersurface. The transition state structures for the addition of CN^- to 2-chloro-2-fluoroacetaldehyde have been calculated to predict theoretically the π-facial stereoselection.