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Open AccessArticle

Synthesis and Structure of Methylsulfanyl Derivatives of Nickel Bis(Dicarbollide)

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., Moscow 119991, Russia
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklay Str., Moscow 117997, Russia
Basic Department of Chemistry of Innovative Materials and Technologies, G.V. Plekhanov Russian University of Economics, 36 Stremyannyi Line, Moscow 117997, Russia
Author to whom correspondence should be addressed.
Dedicated to Professor Bohumil Štibr in the recognition of his outstanding contribution in the carborane chemistry and with very best wishes on the occasion of his 80th birthday.
Academic Editors: Igor B. Sivaev, Narayan S. Hosmane and Bohumír Grűner
Molecules 2019, 24(24), 4449;
Received: 16 November 2019 / Revised: 29 November 2019 / Accepted: 2 December 2019 / Published: 4 December 2019
Symmetrically and unsymmetrically substituted methylsulfanyl derivatives of nickel(III) bis(dicarbollide) (Bu4N)[8,8′-(MeS)2-3,3′-Ni(1,2-C2B9H10)2], (Bu4N)[4,4′-(MeS)2-3,3′-Ni(1,2-C2B9H10)2], and (Bu4N)[4,7′-(MeS)2-3,3′-Ni(1,2-C2B9H10)2] were synthesized, starting from [Ni(acac)2]3 and the corresponding methylsulfanyl derivatives of nido-carborane (Bu4N)[10-MeS-7,8-C2B9H11] and (Bu4N)[10-MeS-7,8-C2B9H11]. Structures of the synthesized metallacarboranes were studied by single-crystal X-ray diffraction and quantum chemical calculations. The symmetrically substituted 8,8′-isomer adopts transoid conformation stabilized by two pairs of intramolecular C–H···S hydrogen bonds between the dicarbollide ligands. The unsymmetrically substituted 4,7′-isomer adopts gauche conformation, which is stabilized by two nonequivalent C–H···S hydrogen bonds and one short chalcogen B–H···S bond (2.53 Å, −1.4 kcal/mol). The gauche conformation was found to be also preferred for the 4,7′-isomer. View Full-Text
Keywords: metallacarboranes; nickel bis(dicarbollide); SMe derivatives; synthesis; structure; hydrogen bonds; chalcogen bonds metallacarboranes; nickel bis(dicarbollide); SMe derivatives; synthesis; structure; hydrogen bonds; chalcogen bonds
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Anufriev, S.A.; Suponitsky, K.Y.; Filippov, O.A.; Sivaev, I.B. Synthesis and Structure of Methylsulfanyl Derivatives of Nickel Bis(Dicarbollide). Molecules 2019, 24, 4449.

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