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Paper | Regular issue | Vol 43, No. 9, 1996, pp.1951-1958
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7531
Hydrogen N-Excange Reaction of Methyl-substituted N-Amino- and N-Methylquinolinium Ions

Wei Wu, Ken-ichi Saeki,* Isamu Terashima, and Yutaka Kawazoe

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan


H-D Exchange rates of the hydrogens of methyl-substituted N-amino-quinolinium ions were comperad with those of the corresponding N-methylquinolinium derivatives. Intreatment carried out below 90°C in phosphate-buffered D2O solvents at pD’s ranging from 3.4 to 11.7, only the ring α-hydrogen and the α- and γ-methyl hydrogens underwent H-D exchange. The N-amino group facilitated exchanges of the ring α-hydrogen several tens of times more than did the N-methyl group, whereas the former facilitated the exchange of substituent methyl hydrogens only several times more than the latter. The pD-dependence of the exchange reactions are described.