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

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

doi:10.1039/C5CP00870K

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

Manolova, Y. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
Kurteva, Vanya B. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
Antonov, Liudmil Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
Marciniak, H. Institut für Physik, Universität Rostock, Germany
Lochbrunner, S. Institut für Physik, Universität Rostock, Germany
Crochet, Aurélien Department of Chemistry, University of Fribourg, Switzerland
Fromm, Katharina M. Department of Chemistry, University of Fribourg, Switzerland
Kamounah, Fadhil S. Department of Science, Systems and Models, Roskilde University, Denmark
Hansen, P. E. Department of Science, Systems and Models, Roskilde University, Denmark

01.04.2015

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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.

Faculty

Faculté des sciences et de médecine

Department

Département de Chimie

Language

English

Classification

Chemistry

License

License undefined

Identifiers

RERO DOC 255817
DOI 10.1039/C5CP00870K

Persistent URL

https://folia.unifr.ch/unifr/documents/304288

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