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

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. Fo...

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Veröffentlicht in:	Physical chemistry chemical physics : PCCP 2015-04, Vol.17 (15), p.10238-10249
Hauptverfasser:	Manolova, Y, Kurteva, V, Antonov, L, Marciniak, H, Lochbrunner, S, Crochet, A, Fromm, K M, Kamounah, F S, Hansen, P E
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetonitrile Dimers Methyl alcohol Physical chemistry Solvents Spectroscopy Tautomers Toluene
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creator	Manolova, Y Kurteva, V Antonov, L Marciniak, H Lochbrunner, S Crochet, A Fromm, K M Kamounah, F S Hansen, P E
description	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 transfer involving the OH group and the piperidine nitrogen occurs. In acetonitrile the equilibrium is predominantly at the OH-form, whereas in methanol the proton transferred tautomer is the preferred form. In chloroform and toluene, the OH form is completely dominant. Both 4-hydroxy-1-naphthaldehyde and 4-methoxy-1-naphthaldehyde (fixed enol form) show dimerization in the investigated solvents and the crystallographic data, obtained for the latter, confirm the existence of a cyclic dimer.
doi_str_mv	10.1039/c5cp00870k
format	Article
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subjects	Acetonitrile Dimers Methyl alcohol Physical chemistry Solvents Spectroscopy Tautomers Toluene
title	4-Hydroxy-1-naphthaldehydes: proton transfer or deprotonation
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