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Intramolecular and intermolecular N-H???F-C hydrogen-bonding interactions in amine adducts of tris(pentafluorophenyl)borane and tris(pentafluorophenyl)alane

Intramolecular and intermolecular N-H???F-C hydrogen-bonding interactions in amine adducts of tris(pentafluorophenyl)borane and tris(pentafluorophenyl)alane
Intramolecular and intermolecular N-H???F-C hydrogen-bonding interactions in amine adducts of tris(pentafluorophenyl)borane and tris(pentafluorophenyl)alane
The reaction between B(C6F5)(3) and NH3(g) in light petroleum yielded the solvated adduct H3N center dot B(C6F5)(3)center dot NH3. Treatment with a second equivalent of B(C6F5)(3) afforded H3N center dot B(C6F5)(3). Attempts to prepare the analogous alane adduct were unsuccessful and resulted in protolysis. Related compounds of the form R'R"N(H)center dot M(C6F5)(3) were synthesized from M(C6F5)(3) and the corresponding primary and secondary amines (M = B, Al; R' = H, Me, CH2Ph; R" = Me, CH2Ph, CH(Me)(Ph); R'R" = cyclo-C5H10). The solid-state structures of 13 new compounds have been elucidated by single-crystal X-ray diffraction and are discussed. Each of the borane adducts has a significant bifurcated intramolecular hydrogen bond between an amino hydrogen and two o-fluorines, while N-(HF)-F-...-C interactions in the alane adducts are weaker and more variable. F-19 NMR studies demonstrate that the borane adducts retain the bifurcated C-(FHF)-H-...-F-...-C hydrogen bond in solution. Compounds of the type R'R"N(H)center dot M(C6F5)(3) conform to Etter's rules for the prediction of hydrogen-bonding interactions.
crystal-structures, polymerization catalysis, olefin polymerization, ammonium complex, b(c6f5)(3), fluorine, water, h2o-center-dot-b(c6f5)(3), metallocene, orientation
0020-1669
5921-5933
Mountford, Andrew J.
6c559853-834a-4810-b819-12d460f79f10
Lancaster, Simon J.
06d860ba-99d7-4be1-a78d-39505c0fc14b
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Horton, Peter N.
48f162d1-d6ce-43c1-aeef-d58b3ec702b8
Hughes, David L.
d3b8245e-976a-47e6-8fe6-6ebcf38e2255
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c
Mountford, Andrew J.
6c559853-834a-4810-b819-12d460f79f10
Lancaster, Simon J.
06d860ba-99d7-4be1-a78d-39505c0fc14b
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Horton, Peter N.
48f162d1-d6ce-43c1-aeef-d58b3ec702b8
Hughes, David L.
d3b8245e-976a-47e6-8fe6-6ebcf38e2255
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Light, Mark E.
13b5eb33-3114-4fb7-8500-90ce69e9933c

Mountford, Andrew J., Lancaster, Simon J., Coles, Simon J., Horton, Peter N., Hughes, David L., Hursthouse, Michael B. and Light, Mark E. (2005) Intramolecular and intermolecular N-H???F-C hydrogen-bonding interactions in amine adducts of tris(pentafluorophenyl)borane and tris(pentafluorophenyl)alane. Inorganic Chemistry, 44 (16), 5921-5933. (doi:10.1021/ic050663n).

Record type: Article

Abstract

The reaction between B(C6F5)(3) and NH3(g) in light petroleum yielded the solvated adduct H3N center dot B(C6F5)(3)center dot NH3. Treatment with a second equivalent of B(C6F5)(3) afforded H3N center dot B(C6F5)(3). Attempts to prepare the analogous alane adduct were unsuccessful and resulted in protolysis. Related compounds of the form R'R"N(H)center dot M(C6F5)(3) were synthesized from M(C6F5)(3) and the corresponding primary and secondary amines (M = B, Al; R' = H, Me, CH2Ph; R" = Me, CH2Ph, CH(Me)(Ph); R'R" = cyclo-C5H10). The solid-state structures of 13 new compounds have been elucidated by single-crystal X-ray diffraction and are discussed. Each of the borane adducts has a significant bifurcated intramolecular hydrogen bond between an amino hydrogen and two o-fluorines, while N-(HF)-F-...-C interactions in the alane adducts are weaker and more variable. F-19 NMR studies demonstrate that the borane adducts retain the bifurcated C-(FHF)-H-...-F-...-C hydrogen bond in solution. Compounds of the type R'R"N(H)center dot M(C6F5)(3) conform to Etter's rules for the prediction of hydrogen-bonding interactions.

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More information

Published date: 8 August 2005
Keywords: crystal-structures, polymerization catalysis, olefin polymerization, ammonium complex, b(c6f5)(3), fluorine, water, h2o-center-dot-b(c6f5)(3), metallocene, orientation

Identifiers

Local EPrints ID: 20871
URI: http://eprints.soton.ac.uk/id/eprint/20871
ISSN: 0020-1669
PURE UUID: 2e4370cd-6cb9-4bb2-8b12-afd61cf24e0a

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Date deposited: 02 Mar 2006
Last modified: 15 Jul 2019 19:25

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Contributors

Author: Andrew J. Mountford
Author: Simon J. Lancaster
Author: Simon J. Coles
Author: Peter N. Horton
Author: David L. Hughes
Author: Michael B. Hursthouse
Author: Mark E. Light

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