The Catalysis of Proton Exchange in Creatinine by General Acids and General Bases
The rate of exchange of methylene protons in creatinine has been followed in D2O by means of proton magnetic resonance spectroscopy over a range of acidity from pD 12.22 to DA –4.24. A plot of the logarithm of the rate against acidity function is in the form of a "W", one wing of which involves reaction of neutral creatinine with hydroxide ion, and the other diprotonated creatinine with water. The central peak represents reaction of protonated creatinine with a molecule of creatinine acting as base. The reaction is subject to catalysis by buffers.The activation of exchange produced by protonating the substrate is designated protonactivatingfactor, p.a.f., and factors affecting its size are discussed in terms of structure.