NBO analysis of the torquoselectivity of the electrocyclic reactions of mono-substituted cyclobutenes

Article type: Research Article

Authors: Saal, Amar^{a; b; *} | Merzoud, Lynda^{a; b}

Affiliations: [a] Laboratory of Computational and Theoretical Chemistry and Photonics, USTHB University of Algiers, Algiers, Algeria | [b] Chemistry Department, UMMTO University of Tizi-Ouzou, Tizi-Ouzou, Algeria

Correspondence: [*] Corresponding author: Amar Saal, Laboratory of Computational and Theoretical Chemistry and Photonics, USTHB University of Algiers, Algiers 16111, Algeria. E-mail:amarsaal@yahoo.fr

Abstract: Conrotatory ring opening of cyclobutene, 3-methoxycyclobutene, and 3-formylcyclobutene has been studied with the density functional theory. The stereoselectivity of these reactions has been elucidated on the basis of the natural bond orbital analysis and correlation diagrams. Hyperconjugative interactions substituent-cyclobutene occurring at the transition state seem to be responsible of these reactions' torquoselectivity.

Keywords: Stereoselectivity, torquoselectivity, electrocyclic reaction, NBO, cyclobutene, DFT calculations

DOI: 10.3233/JCM-160613

Journal: Journal of Computational Methods in Sciences and Engineering, vol. 16, no. 2, pp. 437-447, 2016