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

Synthesis, structure, and supramolecular architecture of benzonitrile and pyridine adducts of bis(pentafluorophenyl)zinc: pentafluorophenyl-aryl interactions versus homoaromatic pairing
Synthesis, structure, and supramolecular architecture of benzonitrile and pyridine adducts of bis(pentafluorophenyl)zinc: pentafluorophenyl-aryl interactions versus homoaromatic pairing
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.
perfluorophenyl stacking interactions, hydrogen-bonding interactions, arene-perfluoroarene interactions, ring polyaromatic, dot-f-c, polymerization catalysts, x-ray-diffraction, coordination polymers, crystal-structures, hydrocarbons, organometallic building-blocks
0276-7333
1436-1446
Martin, Eddy
780401d3-0d8e-46e0-b150-235ba3f33255
Spendley, Claire
c2fe51e7-82b4-4e7d-b66d-b812559d3d37
Mountford, Andrew J.
6c559853-834a-4810-b819-12d460f79f10
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hughes, David L.
d3b8245e-976a-47e6-8fe6-6ebcf38e2255
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Lancaster, Simon J.
06d860ba-99d7-4be1-a78d-39505c0fc14b
Martin, Eddy
780401d3-0d8e-46e0-b150-235ba3f33255
Spendley, Claire
c2fe51e7-82b4-4e7d-b66d-b812559d3d37
Mountford, Andrew J.
6c559853-834a-4810-b819-12d460f79f10
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hughes, David L.
d3b8245e-976a-47e6-8fe6-6ebcf38e2255
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Lancaster, Simon J.
06d860ba-99d7-4be1-a78d-39505c0fc14b

Martin, Eddy, Spendley, Claire, Mountford, Andrew J., Coles, Simon J., Horton, Peter N., Hughes, David L., Hursthouse, Michael B. and Lancaster, Simon J. (2008) Synthesis, structure, and supramolecular architecture of benzonitrile and pyridine adducts of bis(pentafluorophenyl)zinc: pentafluorophenyl-aryl interactions versus homoaromatic pairing. Organometallics, 27 (7), 1436-1446. (doi:10.1021/om701127p).

Record type: Article

Abstract

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.

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More information

Published date: 2008
Keywords: perfluorophenyl stacking interactions, hydrogen-bonding interactions, arene-perfluoroarene interactions, ring polyaromatic, dot-f-c, polymerization catalysts, x-ray-diffraction, coordination polymers, crystal-structures, hydrocarbons, organometallic building-blocks

Identifiers

Local EPrints ID: 54480
URI: http://eprints.soton.ac.uk/id/eprint/54480
ISSN: 0276-7333
PURE UUID: 66ba3b7a-2658-44a9-9489-16d8fa9aa180
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016

Catalogue record

Date deposited: 06 Aug 2008
Last modified: 10 Dec 2019 01:50

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Contributors

Author: Eddy Martin
Author: Claire Spendley
Author: Andrew J. Mountford
Author: Simon J. Coles ORCID iD
Author: Peter N. Horton ORCID iD
Author: David L. Hughes
Author: Simon J. Lancaster

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