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Experimental Evaluation of (L)Au Electron‐Donor Ability in Cationic Gold Carbene Complexes

Carden, Robert G. ; Lam, Nathan ; Widenhoefer, Ross A.

Chemistry : a European journal, 2017-12, Vol.23 (71), p.17992-18001 [Periódico revisado por pares]

Germany: Wiley Subscription Services, Inc

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  • Título:
    Experimental Evaluation of (L)Au Electron‐Donor Ability in Cationic Gold Carbene Complexes
  • Autor: Carden, Robert G. ; Lam, Nathan ; Widenhoefer, Ross A.
  • Assuntos: Aromatic compounds ; Biphenyl ; carbenes ; Cations ; Chemistry ; Electrons ; Fragmentation ; Fragments ; Gold ; Hammett analysis ; sigma stabilization ; Spectroscopy ; Substitutes ; Vinylidene ; vinylidenes
  • É parte de: Chemistry : a European journal, 2017-12, Vol.23 (71), p.17992-18001
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: 29Si NMR spectroscopy was employed to evaluate the electron donor properties of the (L)Au fragments in the cationic gold (β,β‐disilyl)vinylidene complexes [(L)Au=C=CSi(Me)2CH2CH2Si(Me)2]+B(C6F5)4− [L=P(tBu)2o‐biphenyl or NHC] relative to the p‐substituted aryl group in the α‐aryl‐(β,β‐disilyl)vinyl cations [(p‐C6H4X)‐C= CSi(Me)2CH2CH2Si(Me)2]+B(C6F5)4−. Similarly, 19F NMR was employed to evaluate the σ‐ and π‐electron donor properties of the (L)Au fragments in the neutral gold fluorophenyl complexes (L)Au(C6H4F) and in the cationic (fluorophenyl)methoxycarbene complexes [(L)AuC(OMe)(C6H4F)]+SbF6− [L=P(tBu)2o‐biphenyl or IPr] relative to the p‐substituted aryl group of the protonated monofluorobenzophenones [(p‐C6H4X)(C6H4F)COH]+OTf−. The results of these studies indicate that relative to p‐substituted aryl groups, the gold (L)Au fragments [L=P(tBu)2o‐biphenyl or NHC] are significantly more inductively electron donating and are comparable π‐donors and for this reason, the extent of (L)Au→C1 electron donation in gold carbene complexes appears to exceed that provided by a p‐(dimethyamino)phenyl group. Furthermore, the [L=P(tBu)2o‐biphenyl]Au fragment is a nominally stronger electron donor than the (IPr)Au fragment, and both are significantly more inductively electron donating than the (PPh3)Au and [P(OMe)3]Au fragments. Give and you shall receive: Spectroscopic analysis of cationic gold (β,β‐disilyl)vinylidene complexes, gold fluorophenyl complexes, cationic gold flourophenyl(methoxy)carbene complexes, and relevant organic model compounds indicate that (L)Au fragments such as (IPr)Au and [P(tBu)2o‐biphenyl)]Au are strongly inductively electron‐donating, modest π‐donors, and that the net electron‐donor ability of these (L)Au fragments appears to exceed that provided by a p‐(dimethylamino)phenyl group.
  • Editor: Germany: Wiley Subscription Services, Inc
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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