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4-Hydroxy-1-naphthaldehydes: proton transfer or deprotonation

Manolova, Y. ; Kurteva, Vanya B. ; Antonov, Liudmil M. ; Marciniak, H. ; Lochbrunner, S. ; Crochet, Aurélien ; Fromm, Katharina M. ; Kamounah, Fadhil S. ; Hansen, P. E.

In: Physical Chemistry Chemical Physics, 2015, vol. 17, no. 15, p. 10238–10249

A series of naphthaldehydes, including a Mannich base, have been investigated by UV-Vis spectroscopy, NMR and theoretical methods to explore their potential tautomerism. In the case of 4-hydroxy-1-naphthaldehyde concentration dependent deprotonation has been detected in methanol and acetonitrile. For 4-hydroxy-3-(piperidin-1-ylmethyl)-1-naphthaldehyde (a Mannich base) an intramolecular proton...