The first non-enzymatic reduction of acetaldehyde and analogues by an NADH model compound

Abstract

An acid-stable NADH model compound, 9,10-dihydro-10-methylacridine (AcrH₂) efficiently reduces acetaldehyde and analogues in the presence of HClO₄ in acetonitrile to yield 10-methylacridinium ion and the corresponding alcohols; rates of the acid-catalysed reduction of various aliphatic aldehydes and ketones by AcrH₂, which have small primary kinetic isotope effects (k_H/k_D < 2.0), are well correlated with those of the acid-catalysed electron transfer from the excited state of [Ru(bpy)₃]²⁺(bpy 2,2′-bipyridine) to the same substrates.