By P. Hlavica (ed.), L. A. Damani (ed.)
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Additional resources for N-Oxidation of Drugs: Biochemistry, pharmacology, toxicology
Example text
2 ISN-Chemical shifts' and coupling constants (Hz) of N"-hydroxyguanidines (1) (solvent DMSO). 1 No. 3 b Chemical shifts are given in ppm relative to NH]. Signals for two topomers. From Clement and Kampchen (1985). with permission of VCH Verlagsgesellschaft. a b demonstrating that the measured chemical shifts do not represent the average values of two tautomeric forms (Clement, 1986a). The spectrum of N-hydroxydebrisoquine (Ie) (Fig. 2) can only be interpreted in terms of an oxime-type structure.
For example, a well-known reaction which occurs with aliphatic tertiary amine N-oxides and acid anhydrides is the Polonovski reaction, which is illustrated in Fig. 1. Because of the ease with which these reactions occur, it is best to avoid acid anhydrides or acid chlorides at all times when working with samples likely to contain N-oxides. 1 Polonovski reaction with aliphatic tertiary amine N-oxides. 3 TECHNIQUES AVAILABLE FOR THE QUALITATIVE AND QUANTITATIVE ANALYSIS OF INTACT N-OXIDES As mentioned previously, the earlier methods of quantitation almost invariably involved the use of indirect methods of analysis because of the instabilities associated with N-oxides.
J. (1980) Structural studies on isolable (E)-and (Z)-N,N-disubstituted-amidoximes. Crystal and molecular structure of (E)-morpholino-p-nitro-benzamidoxime. J. Chern. Soc. , 2, 704-9. P. and Dorie, J. butylamine compounds; steric and electronic effects. Nouv. J. , 6, 143-7. , Berger, S. and Braun, S. (1984) in 13C-NMR-Spektroskopie, Georg Thieme Verlag, Stuttgart, p. 4. c. L. (1979) in Nitrogen-i5 Nuclear Magnetic Resonance Spectroscopy. John Wiley, New York, pp. 1-33. L. (1983) Nitrogen nuclear magnetic resonance spectroscopy, in The Multinuclear Approach to NMR Spectroscopy (ed.