Surface-enhanced Raman scattering of 4-methoxybenzylcyanide in silver sol

Gold had been considered to be an extremely inert metal, but recently it was found that nanometer-sized gold particles on metal-oxide supports acted as catalysts for simple organic reactions, such as oxidation and hydrogenation, even at or below room temperature. Herein, we report that gold nanoparticles (AuNPs) of zero oxidation state (Au0) are catalytically active for a C--C bond-forming reaction, the cyanosilylation of aldehydes. The AuNP-catalyzed cyanosilylation proceeded smoothly at room temperature with 0.2 wt % loading of AuNPs. The reactions of aromatic aldehydes were almost quantitative, except for benzaldehyde derivatives containing the electron-withdrawing NO2 group, and alpha,beta-unsaturated aromatic aldehydes were the most reactive substrates. The reactions also went smoothly for aliphatic aldehydes. Mechanistic studies indicated that the reactions proceeded both homogeneously and heterogeneously: homogeneous catalysis by leached gold species and heterogeneous catalysis by the adsorption of the reactants (aldehydes and trimethylsilyl cyanide) onto AuNPs. The ratio of homogeneous and heterogeneous catalysis was estimated to be approximately 4:1.

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Gold‐Catalyzed Cyanosilylation Reaction: Homogeneous and Heterogeneous Pathways

Cho

Lee

Kang

et al. 2007

Chemistry A European J

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Adsorption and reaction of 4‐methoxycinnamonitrile on a silver surface: A surface‐enhanced Raman spectroscopic study

Chun

Kim

et al. 1990

J Raman Spectroscopy

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Surface-enhanced Raman scattering of cis-and trans-Qmethoxycinnamonitrile (4MCN) was investigated in aqueous silver sols. Both isomers adsorbed on the silver surface via the cyano group. The adsorption strength for the cis isomer appeared to be greater than that for the trans isomer. However, cis-4MCN, adsorbed selectively on the silver surface, was readily converted to the trans isomer via a laser-assisted surface reaction. The exact mechanism of the photoisomerization is not yet completely understood. It is thought that the reaction occurs via the absorption of a single visible pboton which is in resonance with the low-energy tail of the broadened absorption band of the adsorbed cis isomer.~

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Raman scattering of α‐toluenethiol adsorbed on silver sol

Lee

Kim

1991

J Raman Spectroscopy

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Surface-enhanced Raman scattering (SERS) of a-toluenethiol adsorbed on a silver surface has been investigated. The controversial vibrational assignment of the molecule was refined by comparing the SERS spectra with the ordinary Raman spectra of a-toluenethiol, a-toluenethiolate, benzyl chloride and their deuterated species. Based on tbe assignment and the SERS selection rule, it is proposed that a-toluenethiol is adsorbed as a thiolate on silver via its sulphur atom witb both the methylene group and benzene ring oriented approximately parallel to the metal surface.

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Surface-enhanced Raman scattering of 4-methoxybenzylcyanide in silver sol

Cited by 15 publications

References 35 publications

Gold‐Catalyzed Cyanosilylation Reaction: Homogeneous and Heterogeneous Pathways

Gold‐Catalyzed Cyanosilylation Reaction: Homogeneous and Heterogeneous Pathways

Adsorption and reaction of 4‐methoxycinnamonitrile on a silver surface: A surface‐enhanced Raman spectroscopic study

Raman scattering of α‐toluenethiol adsorbed on silver sol

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