Kinetics of reversible carbon deprotonation of 2-nitroethanol and 2-nitro-1,3-propanediol by hydroxide ion, water, amines, and carboxylate ions. A normal bronsted alpha despite an imbalanced transition state

The kinetic data on the deprotonation of 2-nitroethanol and 2-nitro-1,3-propanediol which concerned the rate of reversible carbon deprotonation by hydroxide ion, water, aminews, and carboxylate ions and pKa values for the ionization at carbon, pK(super CH)(sub a), and oxygen, pK(super OH)(sub a) and ionization of the aci-forms pK(super NOH)(sub a) at 25 degree celsius is reported. The rate constants in the order nitromethane > metroethane > 2-nitropropane is also reported. The rate of proton transfer induced by the substitution of one hydrogen in CH3NO2 by a CH2OH group is also discussed.