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CHEMISTRY AND CHEMICAL ENGINEERING

Abstract

Based on the industrial interest in cyanuric acid derivatives, the aim of the study is to perform a theoretical analysis of cyanuric acid trivinyl esters (2a-4a) and trivinyl cyanurate (2b-4b) using the DFT/defs-TZVP method. The frontier MO analysis, electrostatic potential and analysis of non-covalent interactions in these molecules have been used for consideration of electronic structures of all the compounds. The replacement of H atoms on hydroxyl and imino-groups by a vinyl group of cyanuric acid or its tri-keto form leads to a decrease the n-type MO (subsequently increasing π-type MO) of the starting compounds and the HOMO becomes a π-type MO. However, the introducing of a dichloroethyl group to NH group of the tri-keto form led to enhancing of contribution of unbound electron pairs of chlorine atoms in the HOMO, and the HOMO becomes an n-type MO. The results of the ESP analysis showed the formation of positive π-hole potentials in the case of tri-keto derivatives. The presence of strong attractive and repulsive forces and also weak interactions in the case of tri-vinyl and tri-1,2-dichloroethyl derivatives of tri-keto form have been shown by NCI and RDG plots of investigated compounds. The presence of strong attractive and repulsive forces and also weak interactions in the case of tri-vinyl and tri-1,2-dichloroethyl derivatives of tri-keto form have been shown by NCI and RDG plots of investigated compounds.

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