Model studies of pyridoxal Schiff's bases. Coplanarity and intramolecular hydrogen bonding
- 1 January 1977
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 20 (1) , 176-178
- https://doi.org/10.1021/jm00211a042
Abstract
Interactions between the .pi. cloud of the aromatic ring and the .pi.-electron pair of the imine double bond of aromatic oximes as model compounds of pyridoxal Schiff''s bases were studied by high-resolution 13C magnetic resonance spectroscopy. The coplanarity and intramolecular hydrogen bonding were determined by 13C-1H long-range couplings. This detailed investigation of 13C-1H coupling also provides unambiguous proof of the existence of the enol-imine tautomers in chloroform and dimethyl sulfoxide solutions. The tautomerism between the enol-imine and keto-enamine is discussed.Keywords
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