Health & Environmental Research Online (HERO)


Print Feedback Export to File
1621972 
Technical Report 
Studies on chemical carcinogens and mutagens: 25. Chemoselectivity of alkyl sulfonates toward 4-(p-nitrobenzyl)pyridine in phosphate buffer 
Ninomiya S-I; Kohda, K; Kawazoe, Y 
1984 
HEEP/85/00378 
TOKYO 
TOKYO 
1326-1332 
eng 
HEEP COPYRIGHT: BIOL ABS. Methyl, ethyl, and isopropyl esters of 6 alkanesulfonic acids and 5 p-substituted benzenesulfonic acids were synthesized and their alkylating abilities were evaluated in terms of the chemoselectivity toward 4-(p-nitrobenzyl)pyridine (NBP) in phosphate buffer (pH 6.0) containing 60% acetone. The chemoselectivity constant toward NBP, SNBP, was defined as the logarithm of the ratio of the molar fraction of an alkylating sulfonate, which is consumed for alkylation of NBP vs. the molar fraction of the residual alkylating agent; this is hydrolyzed in the buffer medium. SNBP was not only markedly dependent on the structure of the alkyl moiety of the molecule, but also appreciably dependent on the electronic nature of the leaving sulfonic acid moiety. The structure-chemoselectivity relationship is discussed.