期刊
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
卷 17, 期 15, 页码 10238-10249出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5cp00870k
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资金
- Bulgarian Ministry of Education [HTC02/227]
- DAAD [HTC02/227]
- Swiss National Science Foundation
- Bulgarian National Science Fund [RNF01/0110, UNA-17/2005, DRNF-02-13/2009]
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-1naphthaldehyde 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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