Ab initio investigation of the O–Y (Y = CH3, H) insertion/HI elimination reactions of CH2I–I with CH3OH and H2O: comparison of methanol and water catalyzed reactions

Ab initio calculations for the O–CH3 insertion/HI elimination reactions of CH2I–I with methanol (CH3OH) were done to examine the chemical reactivity of CH2I–I with methanol molecules. It was found that CH2I–I reacts with methanol to form an iodoether (CH2I–OCH3) product and a HI leaving group similar to the O–H insertion/HI elimination reactions of CH2I–I with water. The barrier to reaction decreases as the number of methanol molecules increase suggesting that methanol can catalyze this reaction. A brief comparison of the O–Y (Y = CH3, H) insertion/HI elimination reactions of CH2I–I with methanol to the corresponding reactions with water was done. We found that methanol is less effective in catalysis of the insertion/elimination reactions, which may due to less hydrogen bonding in the methanol solvated clusters compared to water solvated clusters.