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Issue 9, 1992
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The mechanism of exchange of intramolecularly hydrogen-bonded protons in a diamide

Angels González-Lafont  and  José M. Lluch 

Abstract

Two alternative mechanisms for the exchange of intramolecularly hydrogen-bonded protons in a diamide have been theoretically studied by means of the AM1 method. Direct abstraction, and rotation about the C–N bond followed by abstraction, have been considered for both the base-catalysed and the acid-catalysed exchange. From the results obtained in this paper it can be concluded that the base-catalysed exchange takes place by direct abstraction, the internal hydrogen bond clearly retarding the proton exchange. Conversely, the internal hydrogen bond does not appreciably retard acid-catalysed proton exchange.

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Article type: Paper
DOI: 10.1039/P29920001621
Citation: J. Chem. Soc., Perkin Trans. 2, 1992,0, 1621-1624
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    The mechanism of exchange of intramolecularly hydrogen-bonded protons in a diamide

    A. González-Lafont and J. M. Lluch, J. Chem. Soc., Perkin Trans. 2, 1992, 0, 1621
    DOI: 10.1039/P29920001621

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