Journal article
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4-Hydroxy-1-naphthaldehydes: proton transfer or deprotonation
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Manolova, Y.
Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
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Kurteva, Vanya B.
Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
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Antonov, Liudmil
Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
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Marciniak, H.
Institut für Physik, Universität Rostock, Germany
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Lochbrunner, S.
Institut für Physik, Universität Rostock, Germany
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Crochet, Aurélien
Department of Chemistry, University of Fribourg, Switzerland
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Fromm, Katharina M.
Department of Chemistry, University of Fribourg, Switzerland
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Kamounah, Fadhil S.
Department of Science, Systems and Models, Roskilde University, Denmark
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Hansen, P. E.
Department of Science, Systems and Models, Roskilde University, Denmark
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Published in:
- Physical Chemistry Chemical Physics. - 2015, vol. 17, no. 15, p. 10238–10249
English
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.
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Faculty
- Faculté des sciences et de médecine
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Department
- Département de Chimie
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Language
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Classification
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Chemistry
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License
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License undefined
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Identifiers
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Persistent URL
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https://folia.unifr.ch/unifr/documents/304288
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