Heteroaromatic hydrogen exchange reactions. Part V. Isotope effects for the acid-catalysed exchange of 3-3H1-2-methylindole and 3-2H1-2-methylindole

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Abstract
Hydrogen exchange rates are reported for 2-methylindoles labelled with either deuterium or tritium at the 3-position in a range of acetic acid buffer solutions at 25 °C prepared in either H2O or D2O. Various isotopic rate ratios calculated from these data are entirely consistent with an A–SE2 mechanism for the hydrogen exchange, in which the proton is approximately half-transferred to the substrate in the transition state.