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Keto/enol tautomerism in phenylpyruvic acids: structure of the o-nitrophenylpyruvic acid |
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| Authors: | A. J. M. Carpy P. P. Haasbroek J. Ouhabi D. W. Oliver |
| Affiliation: | a Laboratoire de Physico- & Toxico-Chimie des Systèmes Naturels (LPTC), UPRES-A 5472, CNRS, Université de Bordeaux I, 351, Cours de la Libération, 33405 Talence Cedex, France b Department of Pharmacy, Medical School, University of the Witwatersrand, 7 York Road, Parktown 2193, South Africa c Département de Chimie, FST-Guéliz, Université Cadi Ayyad, Avenue Abdelkrim Khattabi, B.P. 618, Marrakech, Morocco d Department of Pharmacology, Potchefstroom University for C.H.E., Potchefstroom 2520, South Africa |
| Abstract: | The synthesis of a tautomeric keto/enol mixture of o-nitrophenylpyruvic acid followed the acid hydrolysis of the azlactone of o-nitrobenzaldehyde was carried out. The structures of the two tautomeric forms were assigned by NMR spectroscopy. X-ray diffraction of a single crystal revealed that the crystalline form corresponds to the keto tautomer. Quantum mechanics calculations in the gas phase confirmed the experimental findings in solution. |
| Keywords: | Phenylpyruvic acids Azlactones Tautomerism NMR X-ray Quantum mechanics |
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