62455-36-1Relevant articles and documents
Reactions of 1,ω-bis(2-bromopyridinium)alkanes with hydroxide ion in aqueous solutions
Fernandez, Carmen,Toscano, Vicente G.,Chaimovich, Hernan,Politi, Mario J.,Hioka, Noboru
, p. 25 - 30 (1998)
The reaction of OH- ion with 1,ω-bis(2-bromopyridinium)alkanes, where the reaction centers are separated by a varying number of methylene groups, was investigated to model the increased velocity of OH- attack on premicellar aggregated N-alkylpyridinium compounds. 1,ω-Bis(2-bromopyridinium)aikanes (RPBr) [R = propane (I), butane (II), pentane (III), hexane (IV) and octane (V)] were synthesized and characterized by standard procedures. The kinetics of I-V with OH- ion fitted two consecutive first-order reactions. The intermediate products, 1-(2-pyridone)-ω-(2-bromopyridinium)alkane, and also the final products 1,ω-bis(2-pyridone)alkanes, were isolated. Deuterium isotope effects, activation parameters and salt effects on the reaction rates suggest that OH- attack is rate limiting and there is a through-space acceleration of the initial attack due to the proximity of the positive charges. These results place an upper limit of 20-fold for the electrostatic acceleration in OH- attack in premicellar aggregates.