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Title: 3-Methylthio-4-phenyl-5-phenylamino-1,2,4-triazole hexabromotellurate:X-ray and computational study
Authors: Fizer, Maksym
Slivka, Mikhailo
Mariychuk, Ruslan
Baumer, Vjacheslav
Lendel, Vasil
Keywords: Synthesis, DFT, Reactivity, Aromaticity, 1,2,4-triazoles, Crystal structure
Issue Date: 5-Jun-2018
Citation: Journal of Molecular Structure 1161, 2018, 226-236
Abstract: Abstract The structure of a newly synthesized 3-methylthio-4-phenyl-5-phenylamino-1,2,4-triazole 1 and its hexabromotellurate salt 2 was investigated. The X-ray diffraction study of 2 gives the insight on the different interaction types in the crystal. The DFT calculations were used for the comprehensive study of the intramolecular and intermolecular forces that are present in the title 3-methylthio-4-phenyl-5-phenylamino-1,2,4-triazole hexabromotellurate. The presence of three different aromatic moieties in the investigated compounds cause π-π stacking interactions which were studied through the Hirshfeld surface analysis and with the discrimination of weak interaction types by filling color to a reduced density gradient (RDG) function isosurface. The RDG in the crystalline state was calculated upon experimental molecular geometry by partitions of the crystal to QM part that was calculated at M06-L/6-311G(d,p) level, and the semi-empirical QM part that was modeled with the PM7 method in QM/MM-like manner. The reactivity of 3-methylthio-4-phenyl-5-phenylamino-1,2,4-triazole and its protonated form was also discussed in terms of conceptual DFT theory and it shows the tendency of sulfur to be the most active center in an electrophilic and radical attack, whereas the site for nucleophilic substitution is medium dependent and not an unequivocal. NICS(1) index was used for the analysis of aromaticity of three different cyclic moieties. The present study insights the changes in the structure of a polyfunctional substituted triazole upon its protonation and explains these changes with the analysis of weak interactions.
Type: Text
Publication type: Стаття
Appears in Collections:Наукові публікації кафедри органічної хімії

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