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Kinetics of the condensation of some aliphatic aldehydes with ammonia

1964; Elsevier BV; Volume: 20; Issue: 6 Linguagem: Inglês

10.1016/s0040-4020(01)99153-7

1464-5416

Y. OGATA, Atsushi Kawasaki,

Photochemistry and Electron Transfer Studies

Abstract The rate and equilibrium constants of the reaction of some aliphatic aldehydes with ammonia have been measured in aqueous solutions at 20° by means of spectrophotometry. The rate equations are ν = kf [unhydrated aldehyde] [free ammonia] for the forward reaction and ν = kr [α-aminoalcohol] for the reverse. The reaction was subject to acid catalysis. Electron-releasing groups in aldehydes tended to decrease the rate of the forward reaction with Taft's ρ* of 2·29, while the same groups increased the rate of the reverse reaction with ρ* of −6·29 (decomposition of α-aminoalcohols). These results agree with the expectation from the suggested reaction mechanism.