The search for electrocatalysis of carbonyl reductions on tin oxide semiconductor electrodes covalently modified with NAD⁺ coenzyme analogs

Seguin, Russell Joseph
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Several N-alkyl-3-carboxamidopyridinyl halides were prepared to serve as NAD⁺ coenzyme model compounds. By varying the electron-withdrawing properties of the alkyl moiety, the electronic properties of these quaternized nicotinamides (i.e., ring current and reduction potential) could be manipulated, as was observed by Nuclear Magnetic Resonance Spectrometry and Cyclic Voltammetry (CV). Several propyltriethoxysilane derivatives were also prepared through linkage to the pyridine's amide moiety. A series of the quaternized nicotinamides were covalently attached to the surface of tin oxide semiconductor electrodes by several silanization methods. The surface coverage was confirmed by X-Ray Photoelectron Spectroscopy and by the appearance of the corresponding CV reduction wave on the electrode's surface. The reduction of several electron deficient carbonyl compounds was investigated upon the NAD⁺ analog electrodes; however, no significant catalysis of the reductions by the enzyme mimic was observed