Stereoselectivity and Regioselectivity of the Cycloaddition Dimerization of allyl 3-(2-pyridyl) acrylate and allyl 3-(2-pyrryl) acrylate: DFT Calculations

International Conference on Materials Engineering and Science

Salim, Haydar A. Mohammad^1 ; Abdallah, Hassan H.^2 ; Ramasami, P.^3

Chemistry Department, College of Science, University of Zahko, Duhok, Iraq^1

Chemistry Department, College of Education, Salahaddin University, Erbil, Iraq^2

Computational Chemistry Group, Department of Chemistry, Faculty of Science, University of Mauritius, Reduit

80837, Mauritius^3

关键词: Conformation analysis;    Density functional theory methods;    IR absorption intensity;    Photochemical dimerization;    Theoretical study;    Thermodynamic parameter;    Vibration frequency;    [2+2] cycloaddition;   

Others  :  https://iopscience.iop.org/article/10.1088/1757-899X/454/1/012049/pdf
DOI  :  10.1088/1757-899X/454/1/012049

来源: IOP

【 摘 要 】

A theoretical study of the photochemical dimerization of allyl 3-(2-pyridyl) acrylate and allyl 3-(2-pyrryl) acrylate is reported. The reactions gave dimers with high regioselectivity and stereoselectivity through [2+2] cycloaddition mechanism. All calculations were computed by density functional theory method, B3LYP, in conjunction with the 6-31G(d) basis set. Conformation analysis, geometric parameters and IR spectrum for the target dimers were also studied. Conformation 2 of allyl 3-(2-pyridyl) acrylate and conformation 9 for allyl 3-(2-pyrryl) acrylate were found to be the most stable structures among the different conformations. Vibration frequencies and IR absorption intensities were calculated for the conformers 2 and 9 using the same computational method. In addition, thermodynamic parameters for the reactions of most stable conformations were analysed. The HOMO and LUMO molecular orbitals and the energy gap between them were estimated for the stable conformations.