Ab Initio Calculation and Spectroscopic Study of the 1,3-Dipolar Cycloaddition Reaction of Benzyl Azide and Acrylic Acid

Abstract

The 1, 3-dipolar cycloaddition reaction of benzyl azide with acrylic acid has been studied using B3LYP (3-21G) density functional theory (DFT). It has been demonstrated that  the reaction leads to the formation of 1-benzyl-1,2,3-triazoline-4-carboxylic acid  at room temperature in the absence of solvent . Upon recrystallization from ethanol the ethyl ester of the product was formed. The structure of the compound was confirmed using IR, UV, ¹H-NMR, ¹³C-NMR and 2D-NMR. The structure of the other possible isomer has been proposed and and both isomers have been studied using Gaussian 03 to predict the possibility of their formation and to calculate the vibrational frequencies and related electronic properties. It has been found that the 1,3-dipolar cycloaddition reaction of benzyl azide with acrylic acid is highly regioselective and spontaneous at 298.15 K and 1 atm.