H and "C NMR studies of N-methyl-substituted hydroxamic acids, RCON(CH,)OH (R = CH,, C,H, and C6Hs), show that the series exhibits &-trans isomerism about the C-N bond. The Z/E ratio increases in the series CH, < C,H, < n-CsH,, < n-C,H,, for a given solvent, indicating that steric interaction betwee
cis–trans Isomerism in monoalkylhydroxamic acids by 1H, 13C and 15N NMR spectroscopy
✍ Scribed by David A. Brown; William K. Glass; Rajeswary Mageswaran; Berhane Girmay
- Publisher
- John Wiley and Sons
- Year
- 1988
- Tongue
- English
- Weight
- 238 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
The first example of cis-truns isomerism in monoalkylhydroxamic acids, detected by 'H, I3C and "N NMR spectroscopy, is reported. The "N NMR spectrum of CH,CO"NHOH gave a clear assignment of the OH and NH protons of both 2 and E isomers. The assignment was confirmed by 'H and "C NMR spectroscopy. A rotational barrier of isomerization (AC,') of 17.8 kcal mol-' was calculated from the variabletemperature 'H NMR spectra using the method of Shanan-Atidi and Bar-Eli.
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