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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
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    01.04.2015
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.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
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Persistent URL
https://folia.unifr.ch/unifr/documents/304288
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