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The structure elucidation of the isomeric mixture of 3-[L-threo-2,3,4-tri -hydroxy-1-(phenyl-hydrazono)butyl] quinoxalin-2(1H)-one in dimethyl sulfoxide solution revisited: experimental and theoretical study

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Abstract

Based on the analyses of 1D and 2D NMR spectra techniques, such as H–H COSY, HSQC, and HMBC of 3-[L-threo-2,3,4-trihydroxy-1-(phenylhydrazono)butyl]- quinoxalin-2(1H)-one in dimethyl sulfoxide solution, it was concluded that this compound exists as a mixture of two isomeric Z- and E- forms I and II rather than the hydrazine imine and diazeny enamine V tautomers reported earlier. The NMR signals assignment was supported using density functional theory.

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Funding

This work is supported by the Deanship of Scientific Research, Taibah University, SA (#7101).

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Taibah University, Yanbu, 46423, Saudi Arabia

    Mohamed A. El-Atawy

  2. Chemistry Department, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria, 21321, Egypt

    Mohamed A. El-Atawy, Abdelrahman H. Hegazi & Adel Amer

  3. Chemistry Department, Faculty of Science, Taibah University, P.O. Box 30002, Al-Munawarah, Al-Madinah, Saudi Arabia

    Abdelrahman H. Hegazi, Mohamed Al Khalaf & Adel Amer

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  1. Mohamed A. El-Atawy
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  2. Abdelrahman H. Hegazi
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  3. Mohamed Al Khalaf
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Correspondence to Mohamed A. El-Atawy or Adel Amer.

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El-Atawy, M.A., Hegazi, A.H., Al Khalaf, M. et al. The structure elucidation of the isomeric mixture of 3-[L-threo-2,3,4-tri -hydroxy-1-(phenyl-hydrazono)butyl] quinoxalin-2(1H)-one in dimethyl sulfoxide solution revisited: experimental and theoretical study. Struct Chem 31, 1065–1072 (2020). https://doi.org/10.1007/s11224-019-01445-3

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