Synthesis and crystal structure of the adduct between 2-pyridyl-selenyl chloride and isobutyro-nitrile

Ayalew W Temesgen; Alexander A Sapronov; Alexey S Kubasov; Alexander S Novikov; Tuan Anh Le; Alexander G Tskhovrebov

doi:10.1107/S2056989024000938

Synthesis and crystal structure of the adduct between 2-pyridyl-selenyl chloride and isobutyro-nitrile

Acta Crystallogr E Crystallogr Commun. 2024 Feb 6;80(Pt 3):247-251. doi: 10.1107/S2056989024000938. eCollection 2024 Mar 1.

Authors

Ayalew W Temesgen¹, Alexander A Sapronov², Alexey S Kubasov³, Alexander S Novikov⁴, Tuan Anh Le⁵, Alexander G Tskhovrebov²

Affiliations

¹ Department of Chemistry, College of Natural and Computational Science, University of Gondar, Gondar 196, Ethiopia.
² Peoples' Friendship University of Russia, 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation.
³ Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 31, 119071 Moscow, Russian Federation.
⁴ Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation.
⁵ University of Science, Vietnam National University, Hanoi, 334 Nguyen Trai, Thanh Xuan, Hanoi, 100000, Vietnam.

Abstract

The reaction between 2-pyridyl-selenenyl chloride and isobutyro-nitrile results in the formation of the corresponding cationic pyridinium-fused 1,2,4-seleno-diazole, namely, 3-(propan-2-yl)-1,2,4-[1,2,4]selena-diazolo[4,5-a]pyridin-4-ylium chloride, C₉H₁₁N₂Se⁺·Cl^-, in high yield (89%). The structure of the compound, established by means of single-crystal X-ray analysis at 100 K, has monoclinic (P2₁/c) symmetry and revealed the presence of bifurcated chalcogen-hydrogen bonding Se⋯Cl^-⋯H-Cl, and these non-covalent contacts were analysed by DFT calculations followed by a topological analysis of the electron-density distribution (ωB97XD/6-311++G** level of theory).

Keywords: 1,2,4-selenodiazole; chalcogen-hydrogen bonding; crystal structure.

Grants and funding

This work was performed under the support of the Russian Science Foundation (award No. 2273-10007).