Structural and computational study of 1,2,4-triazolin-5-thione derivative and its DMSO solvate
| Autor: | Izabela Dybała, Marta Struga, Irena Wawrzycka-Gorczyca |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
010405 organic chemistry
Hydrogen bond Chemistry Organic Chemistry Substituent Aromaticity Crystal structure 010402 general chemistry 01 natural sciences 0104 chemical sciences Analytical Chemistry Inorganic Chemistry Crystal chemistry.chemical_compound Crystallography Computational chemistry X-ray crystallography Molecule Moiety Spectroscopy |
| Zdroj: | Journal of Molecular Structure. 1147:786-796 |
| ISSN: | 0022-2860 |
| DOI: | 10.1016/j.molstruc.2017.07.004 |
| Popis: | The solid state structure of 3-(4-phenyl-5-oxo-1,2,4-triazolin-1-ylmethyl)-4-cyclohexyl-1,2,4-triazolin-5-thione ( 1 ) was characterized by FT-IR and X-ray diffraction experiment. Additionally, molecular and crystal structure of its DMSO solvate ( 1DMSO ) has been determined by X-ray diffraction method. The influence of DMSO molecules incorporation to the crystal lattice on geometry of triazolin-5-thione derivative molecule and crystal packing was analyzed. Non-covalent bonds within the crystals are additionally visualized by determination of Hirshfeld surfaces. According to results of conformational analysis in gas, molecule of triazolin-5-thione derivative adopts the lowest energy conformation in 1DMSO crystal. The crystal structure of 1 and 1DMSO were compared with previously described structurally similar compounds, in which the cyclohexyl substituent was replaced by aromatic one (phenyl/methoxyphenyl). Very interesting differences in molecules association were found by comparing the crystal structures of 1 and 1DMSO with their, mentioned above, aromatic derivatives. Interesting properties of triazolin-5-thione derivatives are connected with their π-electron delocalization effects, thus aromaticity of heterocyclic fragments has been investigated by means of the HOMA index. Comparison of aromaticity calculations results with association tendency of molecules shows that triazolin-5-one fragments reach higher aromaticity when nitrogen atom from this moiety acts as a donor in strong N H⋯N hydrogen bonds. |
| Databáze: | OpenAIRE |
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