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Issue 15, 2015
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4-Hydroxy-1-naphthaldehydes: proton transfer or deprotonation

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Abstract

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.

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

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Publication details

The article was received on 12 Feb 2015, accepted on 12 Mar 2015 and first published on 12 Mar 2015


Article type: Paper
DOI: 10.1039/C5CP00870K
Citation: Phys. Chem. Chem. Phys., 2015,17, 10238-10249
  • Open access: Creative Commons BY license
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    4-Hydroxy-1-naphthaldehydes: proton transfer or deprotonation

    Y. Manolova, V. Kurteva, L. Antonov, H. Marciniak, S. Lochbrunner, A. Crochet, K. M. Fromm, F. S. Kamounah and P. E. Hansen, Phys. Chem. Chem. Phys., 2015, 17, 10238
    DOI: 10.1039/C5CP00870K

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