EventsThe 10th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-10-01403
This submission belongs to the session a. General Organic Synthesis of the event The 10th International Electronic Conference on Synthetic Organic Chemistry
Published date
30 Nov, 2006
Citation
José Elguero, M. Rosario Torres, Elena Pinilla, Rosa M. Claramunt, Dionisia Sanz, Almudena Perona, Protonation Studies of Schiff Bases Using ¹³C and ¹⁵N-NMR Spectroscopy, in Proceedings of The 10th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2006, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-10-01403
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Protonation Studies of Schiff Bases Using 13C and 15N-NMR Spectroscopy

Almudena Perona 1
Dionisia Sanz 1
Rosa M. Claramunt 1
Elena Pinilla 2
M. Rosario Torres 2
José Elguero 3
1. Dpto. de Química Orgánica y Bio-Orgánica, Fac. de Ciencias, UNED, 28040 Madrid, Spain
2. Dpto. de Química Inorgánica, Fac. de Ciencias Químicas, Universidad Complutense, 28040 Madrid, Spain
3. Instituto de Química Médica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain
Abstract
13C and 15N-NMR spectroscopy provides clear evidence that the Schiff bases of 3-hydroxy-4-pyridinecarboxaldehyde exist as a mixture of hydroxyimino and oxoenamino tautomers in acid media. The study of the stabilities of the tautomeric forms has been approached using density functional calculations (B3LYP/6-31G**). The X-ray molecular structure of (E)-4-[(4-bromophenylimino)methyl]-3- hydroxypyridinium tetrafluoroborate has been solved.
Keywords
Schiff bases
Tautomerism
Hydrogen bonds
NMR spectroscopy
Density functional calculations
X-ray
Dimeric Anhydro Bases from Benzothiazole Derivatives
Synthesis of 1-vinyl isoquinolines and isoindolines by cyclization of acyliminium ions derived from allenamides