Structural Chemistry p. 821 - 828 (2014)
Update date:2022-07-29
Topics: Ionic liquid Density functional theory (DFT) B3LYP/6-31G(d,p) Menshutkin reaction S N 2 transition state Five-membered ring transition state Bronsted acidic ILs Esterification, etherification, and Pinacol rearrangement Molecular level understanding Literature Review Mechanistic Insights Spectroscopic Analysis Ionic Liquid Synthesis Properties of the Ionic Liquid Theoretical Calculations Reaction Mechanisms Solvation and Ion Pairing Thermodynamic and Kinetic Analysis Applications and Future Prospects
Singh, Amritpal
Singh, Paramjit
Goel, Neetu
Quaternary ammonium salt obtained from the Menshutkin reaction between DABCO and benzyl chloride has been used in the synthesis of a novel Bronsted acidic ionic liquid (IL), namely 1-benzyl-4-(sulfobutyl)-diaza-bicyclo-octane hydrogen sulfate. The reaction of DABCO with benzyl chloride is a crucial step in the synthesis of this IL. Density functional theory calculations at B3LYP/6-31G(d,p) level have been employed to investigate the mechanism of Menshutkin reaction by calculating the energy barriers through possible transition states i.e., five-membered ring transition state and SN2 transition state in gas phase and in diethyl ether as a solvent. It was found that while DABCO reacts with benzyl chloride through the well-known S N2 transition state mechanism, the corresponding reaction with chlorodiphenylmethane can proceed through both SN2 and five-membered ring transition state mechanism. However, SN2 transition state mechanism is still the strongly preferred one out of the two possible mechanisms. The electronic structure analysis shows that solvent effects and enhanced resonance stabilization may play a decisive role in guiding the reaction pathway.
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