Theoretical Study of Diels-Alder Reaction of But-3-en-2-one with Hexa-1,2,4-triene: A Density Functional Theory Study

Rezan J. Hassan; Hassan H. Abdallah

doi:10.14500/aro.10632

Rezan J. Hassan (1) Department of Chemistry, College of Education, Salahaddin University-Erbil, Erbil 44001, Kurdistan Region. (2) Department of Chemistry, College of Science, Salahaddin University-Erbil, Erbil 44001, Kurdistan Region http://orcid.org/0000-0002-9658-6485
Hassan H. Abdallah Department of Chemistry, College of Education, Salahaddin University-Erbil, Erbil 44001, Kurdistan Region http://orcid.org/0000-0002-9198-0475

Keywords: Cycloaddition, density functional theory calculation, Diels-Alder reaction, mechanism

Abstract

The Diels-Alder reaction between but-3-en-2-one with hexa-1,2,4-triene was studied using density functional theory method at B3LYP-D3/6-311++G(d,p) level of theory. The geometries of the transition states were determined. Moreover, calculations of the vibrational frequencies permitted computation of the activation enthalpies and entropies. The computational results show that the cycloadducts from trans conformer have the lower relative energies (−46.48 and −47.50 kcal/mol) as compared to the cis conformer of cycloadducts (−44.45 and −45.87 kcal/mol). The global reactivity indices were analyzed at the ground state of reactants to predict the reactivity of the studied organic molecules in the cycloaddition reactions. The electronic chemical potential of hexa-1,2,4-trien found to be than but-3-en-2-one, which indicates that the net charge transfer will be from hexa-1,2,4-trien toward the electron-deficient but-3-en-2-one reactant.

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Author Biographies

Rezan J. Hassan, (1) Department of Chemistry, College of Education, Salahaddin University-Erbil, Erbil 44001, Kurdistan Region. (2) Department of Chemistry, College of Science, Salahaddin University-Erbil, Erbil 44001, Kurdistan Region

Rezan J. Hassan is an Assistant Lecturer at the Department of Chemistry, College of Science, Salahaddin University-Erbil. Currently she is a Ph.D. candidate at the Department of Chemistry, College of Education, Salahaddin University-Erbil.

Hassan H. Abdallah, Department of Chemistry, College of Education, Salahaddin University-Erbil, Erbil 44001, Kurdistan Region

Hassan H. Abdallah is a Professor in computational chemistry and drug design at the Department of Chemistry, College of Education, Salahaddin University-Erbil. He has got his Ph.D. and M.Sc. degrees from Bagdad University in Quantum Chemistry. Later he has got post doc positions in computational chemistry and drug design from USA and Malaysia. He has published more than 100 publications in peer reviewed journals and he has supervised many postgraduate students. His research interest is generally, computational chemistry and drug design and focusing more in pandemic viral diseases.

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