Synthesis, structure, and supramolecular architecture of benzonitrile and pyridine adducts of bis(pentafluorophenyl)zinc: pentafluorophenyl–aryl interactions versus homoaromatic pairing

Eddy Martin, Claire Spendley, Andrew J. Mountford, Simon J. Coles, Peter N. Horton, David L. Hughes, Michael B. Hursthouse, Simon J. Lancaster

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Treatment of (C6F5)2Zn(toluene) with 2 equiv of a series of benzonitrile or pyridine derivatives yielded the complexes (C6F5)2Zn(L)2 (where L = benzonitrile, 4-(phenyl)benzonitrile, 4-(N-pyrrolyl)benzonitrile, pyridine, 4-(phenyl)pyridine, and 4-(N-pyrrolyl)pyridine). The four-coordinate solution-phase nature of these complexes was confirmed by a series of variable-temperature 19F NMR experiments and comparison to (C6F5)2Zn(2,2'-bipy). The solvent-free solid-state structures of each of the four-coordinate adducts and the toluene solvate of (C6F5)2Zn(NCC6H4C6H5)2 were determined by single-crystal X-ray diffraction and have distorted tetrahedral geometries. Analysis of the crystal packing revealed a preponderance of offset face-to-face homo-aryl and embrace-like interactions over the hetero-aryl, pentafluorophenyl-phenyl, interaction. These aryl-aryl synthons serve to assemble paired, one- and three-dimensional supramolecular architectures.
Original languageEnglish
Pages (from-to)1436-1446
Number of pages11
Issue number7
Publication statusPublished - 5 Mar 2008

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