Hydrolysis of protonated diazoalkanes: Tracing the mechanism of catalyzed and non-catalyzed reactions

Ansari, Saima and Mallik, Bhabani Shankar (2016) Hydrolysis of protonated diazoalkanes: Tracing the mechanism of catalyzed and non-catalyzed reactions. Masters thesis, Indian Institute of Technology Hyderabad.

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Abstract

The reaction of protonated diazomethane with water and hydroxide spontaneously to give methanol and a nitrogen molecule is being studied computationally. Water attacks as the nucleophile following SN2 mechanism and hydroxide attacks as a base as well as a nucleophile. The structures are optimized using software Gaussian 09. The method applied is DFT B3LYP having basis set 6- 311G +(2d,p). The energies are compared relatively. The final product is found to be -34.7kcal/mol stable than the reactant in case of the methane diazonium ion reacting with two water molecules. In case of hydroxide (nucleophile) the final product is found to be-233.2 kcal/mol stable. Reactions of the cation with hydroxide as a base, yields the product diazomethane and water and the energy of the isolated product is-184.3kcal/mol. The driving force of the reaction is removal of nitrogen molecule as a byproduct (triply bonded, very stable).

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