The Jaffé reaction. Part II. A kinetic study of the Janovsky complexes formed from creatinine(2-imino-1-methylimazolidin-4-one) and acetone

Abstract

Creatinine (2-imino-1-methylimazolidin-4-one) reacts with an alkaline solution of sodium picrate to form a Janovsky complex (the Jaffé reaction). Kinetic studies show that the mechanism at 25° is rate-determining attack of the creatinine anion on picrate. At 35° the rate-determining step may be proton abstraction. Acetone also forms a Janovsky complex with picrate by the same mechanism. Both complexes react further, probably to form 2 : 1 adducts. Reaction between creatinine and an alkaline solution of trinitrobenzene is very fast. The use of the Jaffé reaction for the quantitative estimation of creatinine is discussed critically.