Synthesis and crystal structure of an assembly of three ortho-carborane cages linked via para-phenylene units: effect of aryl orientation on cage C-C bond lengths in C-aryl-ortho-carboranes

Alekseyeva, E.S.; Fox, M.A.; Howard, J.A.K.; MacBride, J.A.H.; Wade, K.

Abstract

The synthesis and crystal and molecular structure are described Of (C2B10H11)C6H4(C2B10H10)C6H4 (C2B10H11) (4), an acyclic assembly of three ortho-carborane units connected through their carbon atoms by two para-phenylene units. For this compound, and published structures of other aryl-ortho-carboranes, correlations are noted between the orientations of aryl substituents and cage carbon-carbon distances (C1-C2). Ab initio RHF/6-31G* and MP2/6-31G* studies on 1-phenyl-ortho-carborane, PhC2B10H11, and other model systems have been used to explore the variations in their energies, C1-C2 bond lengths, and C2-C1-C-aryl bond angles with the orientation of their aryl groups, variations believed to reflect weak interactions between the aryl substituents' pi systems and the carborane cages. The synthesis of a pentafluorophenyl derivative of 4, (C2B10H11)C6H4(C2B10H10)C6H4(C2B10H10)C6F5, is also described.

Citation

Alekseyeva, E., Fox, M., Howard, J., MacBride, J., & Wade, K. (2003). Synthesis and crystal structure of an assembly of three ortho-carborane cages linked via para-phenylene units: effect of aryl orientation on cage C-C bond lengths in C-aryl-ortho-carboranes. Applied Organometallic Chemistry, 17(6-7), 499-508. https://doi.org/10.1002/aoc.467

• Journal Article Type: Article
• Acceptance Date: Feb 20, 2003
• Online Publication Date: May 7, 2003
• Publication Date: 2003-06
• Journal: Applied Organometallic Chemistry
• Print ISSN: 0268-2605
• Electronic ISSN: 1099-0739
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 17
• Issue: 6-7
• Pages: 499-508
• DOI: https://doi.org/10.1002/aoc.467
• Public URL: https://durham-repository.worktribe.com/output/1603933