79757-13-4Relevant academic research and scientific papers
Heats of Reaction of Resonance-Stabilized Carbenium Ions with Nitrogen Bases
Arnett, Edward M.,Venimadhavan, Sampath
, p. 2742 - 2745 (2007/10/02)
Heats of reaction (ΔHrxn) are reported for five resonance-stabilized carbenium ions with ten aliphatic amines and seven pyridines in sulfolane at 25 deg C to produce substituted ammonium ions.Heats of reaction (ΔHrxn) for these neutral bases fall in the same range as the corresponding heats of reaction of the carbenium ions with a variety of resonance-stabilized anions (carbanions, and oxyanions) whose pKas are comparable to those of the amines and pyridines.Although the ΔHrxns do not correlate with the aqueous pKBH(1+)s of the amines, good correlations are obtained using the pKR(1+)s of the carbenium ions and with th e gas-phase heats of reaction of the amines with trimethylboron.Also, the ΔHrxns of pyridines with the carbenium ions correlate fairly well with the pKR(1+)s of the carbenium ions and are surprisingly insensitive to steric hindrance.
