A fluorine-19 nuclear magnetic resonance study of inductive and mesomeric effects in tertiary phosphine gold phenyl complexes

Nichols, D. I.

doi:10.1039/j19700001216

Cited by 16 publications

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“…Howeverd ata for the (PR 3 )Au and (NHC)Au fragments germane to gold(I) catalysis are absent. [38,39] To determine the inductive (s i )a nd resonance (s r )s ubstituent parameters for (L)Au fragments, we synthesized an eightmembered family of gold m-a nd p-fluorophenyl complexes (Table 2). [40] The 19 FNMR chemical shifts (d m and d p )a nd the associated inductive (s i )a nd resonance parameters (s r )o fc omplexes 17 and values for L = P(OPh 3 ) 3 taken from the literaturea re compiled in Ta ble 2.…”

Section: Neutral Gold Fluorophenyl Complexesmentioning

confidence: 99%

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

Carden

Lam

Widenhoefer

2017

Chemistry A European J

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Si 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) CH CH Si(Me) ] B(C F ) [L=P(tBu) o-biphenyl or NHC] relative to the p-substituted aryl group in the α-aryl-(β,β-disilyl)vinyl cations [(p-C H X)-C= CSi(Me) CH CH Si(Me) ] B(C F ) . Similarly, F 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(C H F) and in the cationic (fluorophenyl)methoxycarbene complexes [(L)AuC(OMe)(C H F)] SbF [L=P(tBu) o-biphenyl or IPr] relative to the p-substituted aryl group of the protonated monofluorobenzophenones [(p-C H X)(C H F)COH] OTf . The results of these studies indicate that relative to p-substituted aryl groups, the gold (L)Au fragments [L=P(tBu) o-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) o-biphenyl]Au fragment is a nominally stronger electron donor than the (IPr)Au fragment, and both are significantly more inductively electron donating than the (PPh )Au and [P(OMe) ]Au fragments.

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Section: Neutral Gold Fluorophenyl Complexesmentioning

confidence: 99%

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

Carden

Lam

Widenhoefer

2017

Chemistry A European J

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“…Trip/zen^/phosphinegold(I) trimethylsilanolate (2), as prepared by the same procedure (75%, mp 145-147°), has very similar characteristics. The arsenic analog (C6Hó)3As-»-Au-0-Si(CH3)3 ( 3), mp 140-143°d ec, is of more limited thermal stability.…”

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confidence: 99%

Organosilicon compounds containing monovalent gold

Schmidbaur¹,

Shiotani²

1970

J. Am. Chem. Soc.

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ChemInform Abstract: (19)F‐NMR‐UNTERSUCHUNG DER INDUKTIVEN UND MESOMEREN EFFEKTE IN PHENYL‐GOLD‐KOMPLEXEN MIT TERT. PHOSPHINEN

Nichols¹

1970

Chemischer Informationsdienst. Organische Chemie

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A fluorine-19 nuclear magnetic resonance study of inductive and mesomeric effects in tertiary phosphine gold phenyl complexes

Cited by 16 publications

References 0 publications

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

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

Organosilicon compounds containing monovalent gold

ChemInform Abstract: (19)F‐NMR‐UNTERSUCHUNG DER INDUKTIVEN UND MESOMEREN EFFEKTE IN PHENYL‐GOLD‐KOMPLEXEN MIT TERT. PHOSPHINEN

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