TY - JOUR
T1 - The mechanism of exchange of intramolecularly hydrogen-bonded protons in a diamide
AU - González-Lafont, Angels
AU - Lluch, José M.
PY - 1992/12/1
Y1 - 1992/12/1
N2 - 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.
AB - 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.
M3 - Article
SN - 1472-779X
SP - 1621
EP - 1624
JO - Journal of the Chemical Society, Perkin Transactions 2 (2001)
JF - Journal of the Chemical Society, Perkin Transactions 2 (2001)
IS - 9
ER -