KINETIC AND EQUILIBRIUM STUDIES OF THE PROTON AND DEUTERON TRANSFER-REACTION BETWEEN BIS(2,4-DINITROPHENYL)METHANE AND STRONG NITROGEN BASES IN ACETONITRILE

Deprotonation of bis(2,4-dinitrophenyl)methane (C-acid) by tetramethylguanidine (TMG), 1,2-bis(dimethyl-aminomethyl)benzene (DMAMB) and 1,8-bis(dimethylamino)naphthalene (DMAN) in acetonitrile was studied by visible, H-1 NMR and FT-IR spectroscopy. The mixture of TMG with C-acid forms a protonated base and a product, which was different when compared with the mixtures of DMAMB or DMAN with C-acid. The spectral feature was explained as a strong electrostatic interaction between the product and the protonated TMG. Kinetic and equilibrium measurements of the reactions of C-acid with TMG, DMAMB and DMAN were completed and the kinetic isotope effects k(H)/k(D) are reported.