G. Barlin, J. A. Benbow
1975
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0
Influential Citations
3
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
Kinetics of the replacement reactions of chloro-, iodo-, methoxy-, and methylthio-subsittuted N-methylquinolinium and N-methylisoquinolinium iodides with hydroxide ions have been determined. The 2-iodo- and 2-methylthioquinolinium salts at 20° were 1440 and 1490 times more reactive than their 4-isomers respectively, owing to lower energies of activation and higher frequency factors. The reactivity of 1-methylthioisoquinoline methiodide was anomalous, being 530 times greater than that of 2-methylthioquinoline methiodide. N-Methylation of the iodoquinolines and -isoquinolines increased their reactivity towards hydroxide ions at 114·8° by 1·2–3·4 × 107 fold for substituents at the α-position, and 6·1 × 105 fold for substituents at the γ-position of quinoline. U.v. and 1H n.m.r. spectra are recorded and discussed.