On November 20, 1996, Bernasconi, Claude F.; Wenzel, Philip J. published an article.Synthetic Route of 13544-06-4 The title of the article was Kinetics of Proton Transfer from 2-Nitro-4-X-phenylacetonitriles to Piperidine and Morpholine in Aqueous Me2SO. Solvent and Substituent Effects on Intrinsic Rate Constants. Transition State Imbalances. And the article contained the following:
Rate constants (k1B) for the deprotonation of 2-nitro-4-X-phenylacetonitrile, 2-X (X = NO2, SO2CH3, CN, CF3, Br, and Cl) by piperidine and morpholine and for the reverse reaction (k-1BH) have been determined in 90% Me2SO-10% water, 50% Me2SO-50% water, and water (X = NO2, SO2CH3, CN only). Broensted 尾B values (dlog k1B/dpKaBH), Broensted 伪CH values (dlog k1B/dlog KaCH), and intrinsic rate constants (log ko = log(k1/q) for pKaBH – pKaCH + log(p/q) = 0) were calculated from these data. 伪CH Is smaller than 尾B, implying an imbalance which is consistent with a transition state in which delocalization of the neg. charge into the 2-nitrophenyl moiety lags behind proton transfer. A consequence of this imbalance is that the intrinsic rate constant decreases with increasing electron withdrawing strength of X. For 蟺-acceptor substituents (NO2, SO2CH3, CN) there is a further decrease in ko due to a lag in the delocalization of the charge into X. The intrinsic rate constants depend very little on the Me2SO content of the solvent which is shown to be the result of compensation of mainly two competing factors. One is the stabilization of the polarizable transition state by the polarizable Me2SO which increases ko; the other is attributed to a lag in the solvation of the developing carbanion behind proton transfer at the transition state which leads to a decrease in ko. The experimental process involved the reaction of 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile(cas: 13544-06-4).Synthetic Route of 13544-06-4
The Article related to deprotonation nitrophenylacetonitrile piperidine kinetics mechanism, broensted lfer deprotonation nitrophenylacetonitrile, solvent effect deprotonation nitrophenylacetonitrile and other aspects.Synthetic Route of 13544-06-4
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts