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Semenov VA, Samultsev DO, Rulev AY, et al. Theoretical and experimental (15)N NMR study of enamine-imine tautomerism of 4-trifluoromethyl[b]benzo-1,4-diazepine system. Magn Reson Chem. 2015;53(12):1031-4doi: 10.1002/mrc.4296.
Semenov, V. A., Samultsev, D. O., Rulev, A. Y., & Krivdin, L. B. (2015). Theoretical and experimental (15)N NMR study of enamine-imine tautomerism of 4-trifluoromethyl[b]benzo-1,4-diazepine system. Magnetic resonance in chemistry : MRC, 53(12), 1031-4. https://doi.org/10.1002/mrc.4296
Semenov, Valentin A, et al. "Theoretical and experimental (15)N NMR study of enamine-imine tautomerism of 4-trifluoromethyl[b]benzo-1,4-diazepine system." Magnetic resonance in chemistry : MRC vol. 53,12 (2015): 1031-4. doi: https://doi.org/10.1002/mrc.4296
Semenov VA, Samultsev DO, Rulev AY, Krivdin LB. Theoretical and experimental (15)N NMR study of enamine-imine tautomerism of 4-trifluoromethyl[b]benzo-1,4-diazepine system. Magn Reson Chem. 2015 Dec;53(12):1031-4. doi: 10.1002/mrc.4296. Epub 2015 Aug 20. PMID: 26290420.
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Magn Reson Chem. 2015 Dec;53(12):1031-4. doi: 10.1002/mrc.4296. Epub 2015 Aug 20.

Theoretical and experimental (15)N NMR study of enamine-imine tautomerism of 4-trifluoromethyl[b]benzo-1,4-diazepine system.

Magnetic resonance in chemistry : MRC

Valentin A Semenov, Dmitry O Samultsev, Alexander Yu Rulev, Leonid B Krivdin

Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky St. 1, 664033, Irkutsk, Russia.

PMID: 26290420 DOI: 10.1002/mrc.4296

Abstract

The tautomeric structure of 4-trifluoromethyl[b]benzo-1,4-diazepine system in solution has been evaluated by means of the calculation of (15)N NMR chemical shifts of individual tautomers in comparison with the averaged experimental shifts to show that the enamine-imine equilibrium is entirely shifted toward the imine form. The adequacy of the theoretical level used for the computation of (15)N NMR chemical shifts in this case has been verified based on the benchmark calculations in the series of the push-pull and captodative enamines together with related azomethynes, which demonstrated a good to excellent agreement with experiment.

Copyright © 2015 John Wiley & Sons, Ltd.

Keywords: 15N NMR; GIAO-DFT; chemical shift; enamine-imine tautomerism; enamines; shielding constant; trifluoromethyl[b]benzo-1,4-diazepines

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