cis–trans Isomerism in monoalkylhydroxamic acids by 1H, 13C and 15N NMR spectroscopy
- 1 November 1988
- journal article
- research article
- Published by Wiley in Magnetic Resonance in Chemistry
- Vol. 26 (11) , 970-973
- https://doi.org/10.1002/mrc.1260261107
Abstract
The first example of cis–trans isomerism in monoalkylhydroxamic acids, detected by 1H, 13C and 15N NMR spectroscopy, is reported. The 15N NMR spectrum of CH3CO15NHOH gave a clear assignment of the OH and NH protons of both Z and E isomers. The assignment was confirmed by 1H and 13C NMR spectroscopy. A rotational barrier of isomerization (ΔGc≠) of 17.8 kcal mol−1 was calculated from the variable‐temperature 1H NMR spectra using the method of Shanan‐Atidi and Bar‐Eli.Keywords
This publication has 10 references indexed in Scilit:
- Index / Chemistry and Biology of Hydroxamic AcidsPublished by S. Karger AG ,2015
- Design of metal chelates with biological activity. 5. Complexation behavior of dihydroxamic acids with metal ionsInorganic Chemistry, 1986
- Conformation and dynamics of carcinogenic N-substituted 2-aminofluorene compounds studied by NMR.Journal of the American Chemical Society, 1983
- Proton polarization transfer in natural abundance 15N NMR studies of E‐ and Z‐isomers of N‐alkylformamidesMagnetic Resonance in Chemistry, 1981
- The Chemistry of Hydroxamic Acids and N‐HydroxyimidesAngewandte Chemie International Edition in English, 1974
- Über die Struktur der Thioamide und ihrer Derivate, XII1) Untersuchungen zur behinderten Rotation bei ThiohydroxamsäurenEuropean Journal of Organic Chemistry, 1971
- The crystal structure of acetohydroxamic acid hemihydrateActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 1970
- A convenient method for obtaining free energies of activation by the coalescence temperature of an unequal doubletThe Journal of Physical Chemistry, 1970
- Hindered rotation in NO-diacylhydroxylaminesChemical Communications (London), 1967
- cis and trans Configurations of the Peptide Bond in N-Monosubstituted Amides by Nuclear Magnetic ResonanceJournal of the American Chemical Society, 1964