Title of article :
Ab Initio Calculation and Spectroscopic Study of the 1,3-Dipolar Cycloaddition Reaction of Benzyl Azide and Acrylic Acid
Author/Authors :
Shriteh, Thanaa Albaath University - Faculty of Science - Department of Chemistry, Syria , Kodlaa, Adnan Albaath University - Faculty of Sciences - Department of chemistry, Syria , Abu-Orabi, Sultan T. Yarmouk University - Faculty of Science - Department of Chemistry, Jordan , Madwar, Rushdi Albaath University - Faculty of Science - Department of Chemistry, Syria , Atfeh, Adnan International University of Scienceand Technology - Faculty of Pharmacy - Department of Basic and Clinical Sciences, Syria
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.
Keywords :
Triazoline , 1,3 , Dipolar cycloaddition , Activation energy , DFT , Benzyl azide
Journal title :
Jordan Journal of Chemistry
Journal title :
Jordan Journal of Chemistry
