A gold-197 Moessbauer study of a series of isocyanide, carbene, or methanide derivatives of gold. The crystal structure of trans,trans- and cis,cis-[(carbene)2Au]ClO4 and of cis,trans-(carbene)AuCl (carbene = p-MeC6H4NHCOEt)

Banditelli, Guido; Bonati, Flavio; Calogero, Sandro; Valle, Giovanni; Wagner, F. E.; Wordel, R.

doi:10.1021/om00138a009

Cited by 23 publications

(8 citation statements)

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“…In the 13 C{ 1 H} NMR spectra of complexes 8 and 9, the signals of the C 6 F 5 ligand are very weak and are partly visible as a series of multiplets due to coupling of the 19 F nuclei with the carbon nuclei. The 13 C chemical shifts of the neutral and cationic carbene complexes 7 and 8 are once again very similar.…”

Section: Resultsmentioning

confidence: 99%

“…Still, other authors draw single bonds between all of the atoms bonded to the carbene carbon . There is general consensus that π-back-donation in carbene, carbonyl, and isocyanide complexes of gold occurs only to a limited extent, , and thus, representation of these compounds by a metal−carbon double bond is certainly inaccurate. In this paper, we have chosen to call a number of the new compounds carbene complexes and have chosen to represent them by single metal−carbon bonds, as well as positive charges being located on the nitrogen atoms.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of Thienyl Oligomeric, Carbene, and Nitrogen-Donor Complexes of Gold(I)

Desmet¹,

Raubenheimer²,

Kruger³

1997

Organometallics

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Reaction of [AuCl(tht)] (tht = tetrahydrothiophene) with 2-(4‘,5‘-dihydro-4‘,4‘-dimethyl-2‘-oxazolinyl)thien-5-yllithium or 2-(4‘,5‘-dihydro-4‘,4‘-dimethyl-2‘-oxazolinyl)thien-3-yllithium afforded thienyl dimeric and trimeric oligomers of gold(I). Protonation of these compounds as well as the stable monomers obtained from [Au(C6F5)(tht)] or [AuCl(PPh3)] afforded unique diorganocarbene complexes as well as nitrogen-donor compounds, the former being unusual divinylcarbene complexes. Reaction of 2-(2‘-pyridyl)thien-5-yllithium with [AuCl(PPh3)] produced, upon alkylation, organothiocarbene compounds. The molecular structure of the dimeric a Au···Au separation of 2.8450(6) Å.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Thienyl Oligomeric, Carbene, and Nitrogen-Donor Complexes of Gold(I)

Desmet¹,

Raubenheimer²,

Kruger³

1997

Organometallics

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“…They w ere im portant sources for the preparation o f bis(carbene) co m plexes o f gold(I) [3,4], and in 1986 their use as starting m aterials and catalysts for the synthesis o f chiral oxazolines was dem onstrated [5]. The struc ture of the cations [R N C A uC N R ]+ in these co m plexes was assum ed to be linear, but no struc ture determ ination has been undertaken.…”

Section: Introductionmentioning

confidence: 99%

Structural Investigation of Bis(isonitrile)gold(I) Complexes

Schneider

Sladek

Bauer

et al. 1997

Zeitschrift Für Naturforschung B

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The reaction of (MeNC)-, (PhNC)-and (MesNC)AuCl in tetrahydrofuran with an equimolar amount of the corresponding isonitrile ligand and one equivalent of Ag+X~ (X -= BF^ or CF3S O J) leads to the formation of the bis(isonitrile)gold(I) complexes (MeNC)aAu+ CFiSO( 1), (PhNC)2Au+ BF^ (2) and (M esNC)2Au+ BF^ (3). The crystal structures of 1, 2 and 3 have been determined. In compound 1 there are rod-like cations with a parallel packing into meandering puckered layers, in which the gold atoms have alternating A u-A u contacts of 3.611 and 3.624 A. In complex 2 the cations form long double-paddles, with the two paddles at an angle of 11.5°. The individual cations are well separated and have no sub-van-der-Waals A u-A u contacts. The crystal structure of 3 is similar, but with a smaller dihedral angle between the planes of the two mesityl rings (56.0°).

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“…The gold(I) acyclic aminooxy carbene complexes of the type (AAOC)AuCl are primarily prepared by (i) in situ deprotonation of the corresponding methanaminium salt with LiHMDS followed by the treatment with (Me 2 S)AuCl and (ii) by the direct reaction of ionic gold(I) isocyanide complexes with alcohols derivatives. , In this regard, all of the gold(I) (AAOC)AuCl-type complexes, ( 1 – 4 ) b , were conveniently obtained by the in situ deprotonation method from {[(4-R 2 -2,6- t -Bu 2 -C 6 H 2 O)(N(R 1 ) 2 )]CH} + OTf – ( 1 – 4 ) a in ca . 26–62% yield.…”

Section: Resultsmentioning

confidence: 99%

Accessing Bioactive Hydrazones by the Hydrohydrazination of Terminal Alkynes Catalyzed by Gold(I) Acyclic Aminooxy Carbene Complexes and Their Gold(I) Arylthiolato and Gold(III) Tribromo Derivatives: A Combined Experimental and Computational Study

et al. 2023

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Hydrohydrazination of terminal alkynes with hydrazides yielding hydrazones 5–14 were successfully catalyzed by a series of gold(I) acyclic aminooxy carbene complexes of the type [{(4-R2-2,6-t-Bu2-C6H2O)(N(R1)2)}methylidene]AuCl, where R2 = H, R1 = Me (1b); R2 = H, R1 = Cy (2b); R2 = t-Bu, R1 = Me (3b); R2 = t-Bu, R1 = Cy (4b). The mass spectrometric evidence corroborated the existence of the catalytically active solvent-coordinated [(AAOC)Au(CH3CN)]SbF6 (1–4)A species and the acetylene-bound [(AAOC)Au(HCCPhMe)]SbF6 (3B) species of the proposed catalysis cycle. The hydrohydrazination reaction was successfully employed in synthesizing several bioactive hydrazone compounds (15–18) with anticonvulsant properties using a representative precatalyst (2b). The DFT studies favored the 4-ethynyltoluene (HCCPhMe) coordination pathway over the p-toluenesulfonyl hydrazide (NH2NHSO2C6H4CH3) coordination pathway, and that proceeded by a crucial intermolecular hydrazide-assisted proton transfer step. The gold(I) complexes (1–4)b were synthesized from the {[(4-R2-2,6-t-Bu2-C6H2O)(N(R1)2)]CH}+OTf– (1–4)a by treatment with (Me2S)AuCl in the presence of NaH as a base. The reactivity studies of (1–4)b yielded the gold(III) [{(4-R2-2,6-t-Bu2-C6H2O)(N(R1)2)}methylidene]AuBr3 (1–4)c complexes upon reaction with molecular bromine and the gold(I) perfluorophenylthiolato derivatives, [{(4-R2-2,6-t-Bu2-C6H2O)(N(R1)2)}methylidene]AuSC6F5 (1–4)d, upon treatment with C6F5SH.

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A gold-197 Moessbauer study of a series of isocyanide, carbene, or methanide derivatives of gold. The crystal structure of trans,trans- and cis,cis-[(carbene)2Au]ClO4 and of cis,trans-(carbene)AuCl (carbene = p-MeC6H4NHCOEt)

Cited by 23 publications

References 1 publication

Synthesis and Characterization of Thienyl Oligomeric, Carbene, and Nitrogen-Donor Complexes of Gold(I)

Synthesis and Characterization of Thienyl Oligomeric, Carbene, and Nitrogen-Donor Complexes of Gold(I)

Structural Investigation of Bis(isonitrile)gold(I) Complexes

Accessing Bioactive Hydrazones by the Hydrohydrazination of Terminal Alkynes Catalyzed by Gold(I) Acyclic Aminooxy Carbene Complexes and Their Gold(I) Arylthiolato and Gold(III) Tribromo Derivatives: A Combined Experimental and Computational Study

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