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.

doi:10.1039/b411099d

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.

Authors

A.S. Batsanov

Dr Mark Fox m.a.fox@durham.ac.uk
Assistant Professor

T.G. Hibbert

J.A.K. Howard

R. Kivekäs

A. Laromaine

R. Sillanpää

C. Viñas

K. Wade

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