Sulfur, tin and gold derivatives of 1-(2′-pyridyl)-ortho-carborane, 1-R-2-X-1,2-C2B10H10 (R = 2′-pyridyl, X = SH, SnMe3 or AuPPh3)

Batsanov, A.S.; Fox, M.A.; Hibbert, T.G.; Howard, J.A.K.; Kivekäs, R.; Laromaine, A.; Sillanpää, R.; Viñas, C.; Wade, K.

Abstract

Reaction of the lithium salt of 1-(2′-pyridyl)-ortho-carborane, Li[1-R-1,2-C2B10H10] (R = 2′-NC5H4), with sulfur, followed by hydrolysis, gave the mercapto-o-carborane, 1-R-2-SH-1,2-C2B10H10 which forms chiral crystals containing helical chains of molecules linked by intermolecular S–HN hydrogen bonds. The cage C(1)–C(2) and exo C(2)–S bond lengths (1.730(3) and 1.775(2) Å, respectively) are indicative of exo S[double bond, length as m-dash]C π bonding. The tin derivative 1-R-2-SnMe3-1,2-C2B10H10, prepared from Li[1-R-1,2-C2B10H10] and Me3SnCl, crystallises with no significant intermolecular interactions. The pyridyl group lies in the C(1)–C(2)–Sn plane, oriented to minimise the NSn distance (2.861(3) Å). The tin environment is distorted trigonal bipyramidal with axial N and Me. The gold derivative 1-R-2-AuPPh3-1,2-C2B10H10, prepared from Li[1-R-1,2-C2B10H10] and AuCl(PPh3), reveals no NAu interaction in its crystal structure.

Citation

Batsanov, A., Fox, M., Hibbert, T., Howard, J., Kivekäs, R., Laromaine, A., …Wade, K. (2004). Sulfur, tin and gold derivatives of 1-(2′-pyridyl)-ortho-carborane, 1-R-2-X-1,2-C2B10H10 (R = 2′-pyridyl, X = SH, SnMe3 or AuPPh3). Dalton Transactions, 2004(22), 3822-3828. https://doi.org/10.1039/b411099d

• Journal Article Type: Article
• Acceptance Date: Sep 28, 2004
• Publication Date: Oct 15, 2004
• Deposit Date: Dec 14, 2011
• Publicly Available Date: Jun 1, 2015
• Journal: Dalton Transactions
• Print ISSN: 1477-9226
• Electronic ISSN: 1477-9234
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 2004
• Issue: 22
• Pages: 3822-3828
• DOI: https://doi.org/10.1039/b411099d
• Public URL: https://durham-repository.worktribe.com/output/1533070