Ethenoadenine Precursor 7,8-dihydro-8-hydroxy-imidazo[2,1-i]purine dehydration

The reaction of chloroacetaldehyde with adenine to form ethenoadenine has been modelled: this is an intrinsic reaction coordinate at the 6-31G(d) level of theory using the wB97X-D functional in water. When chloroacetaldehyde reacts with adenine to form ethenoadenine the reaction can proceed by one of two routes dependent upon the orientation of the chloroacetaldehyde molecule with the adenine molecule. This model is based upon an orientation which would form the intermediate 7,8-dihydro-8-hydroxy-imidazo[2,1-i]purine. This model also uses an explicit water molecule in the elimination reaction.