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“Hummingbird” Behaviour of N-Heterocyclic Carbenes Stabilises Out-of-Plane Bonding of AuCl and CuCl Units

Abstract : An N-heterocyclic carbene substituted by two expanded 9-ethyl-9-fluorenyl groups was shown to bind an AuCl unit in an unusual manner, namely with the AuX rod sitting out of the plane defined by the heterocyclic carbene unit. As shown by X-ray studies and DFT calculations, the observed large pitch angle (21°) arises from an easy displacement of the gold(I) atom away from the carbene lone-pair axis, combined with the stabilisation provided by weak CH⋅⋅⋅Au interactions involving aliphatic and aromatic H atoms of the NHC wingtips. Weak, intermolecular Cl⋅⋅⋅H bonds are likely to cooperate with the H⋅⋅⋅Au interactions to stabilise the out-of-plane conformation. A general belief until now was that tilt angles in NHC complexes arise mainly from steric effects within the first coordination sphere
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01225625
Contributor : Laurent Jonchère <>
Submitted on : Friday, November 6, 2015 - 2:08:43 PM
Last modification on : Thursday, May 28, 2020 - 10:56:02 AM

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Matthieu Teci, Eric Brenner, Dominique Matt, Christophe Gourlaouen, Loic Toupet. “Hummingbird” Behaviour of N-Heterocyclic Carbenes Stabilises Out-of-Plane Bonding of AuCl and CuCl Units. Chemistry - A European Journal, Wiley-VCH Verlag, 2015, 21 (31), pp.10997--11000. ⟨10.1002/chem.201500840⟩. ⟨hal-01225625⟩

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