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Kozlecki T, Tolstoy PM, Kwocz A, et al. Conformational state of β-hydroxynaphthylamides: Barriers for the rotation of the amide group around CN bond and dynamics of the morpholine ring. Spectrochim Acta A Mol Biomol Spectrosc. 2015;149:254-62doi: 10.1016/j.saa.2015.04.052.
Kozlecki, T., Tolstoy, P. M., Kwocz, A., Vovk, M. A., Kochel, A., Polowczyk, I., Tretyakov, P. Y., & Filarowski, A. (2015). Conformational state of β-hydroxynaphthylamides: Barriers for the rotation of the amide group around CN bond and dynamics of the morpholine ring. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 149254-62. https://doi.org/10.1016/j.saa.2015.04.052
Kozlecki, Tomasz, et al. "Conformational state of β-hydroxynaphthylamides: Barriers for the rotation of the amide group around CN bond and dynamics of the morpholine ring." Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy vol. 149 (2015): 254-62. doi: https://doi.org/10.1016/j.saa.2015.04.052
Kozlecki T, Tolstoy PM, Kwocz A, Vovk MA, Kochel A, Polowczyk I, Tretyakov PY, Filarowski A. Conformational state of β-hydroxynaphthylamides: Barriers for the rotation of the amide group around CN bond and dynamics of the morpholine ring. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Oct 05;149:254-62. doi: 10.1016/j.saa.2015.04.052. Epub 2015 Apr 28. PMID: 25965172.
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Spectrochim Acta A Mol Biomol Spectrosc. 2015 Oct 05;149:254-62. doi: 10.1016/j.saa.2015.04.052. Epub 2015 Apr 28.

Conformational state of β-hydroxynaphthylamides: Barriers for the rotation of the amide group around CN bond and dynamics of the morpholine ring.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy

Tomasz Kozlecki, Peter M Tolstoy, Agnieszka Kwocz, Mikhail A Vovk, Andrzej Kochel, Izabela Polowczyk, Peter Yu Tretyakov, Aleksander Filarowski

Affiliations

  1. Wroclaw University of Technology, Faculty of Chemistry, Division of Chemical Engineering, 50-373 Wroc?aw, Poland.
  2. St. Petersburg State University, Center for Magnetic Resonance, 198504 St. Petersburg, Russia. Electronic address: [email protected].
  3. Faculty of Chemistry, University of Wroc?aw, 50-383 Wroc?aw, Poland.
  4. St. Petersburg State University, Center for Magnetic Resonance, 198504 St. Petersburg, Russia.
  5. University of Architecture and Civil Engineering, 625001 Tyumen, Russia.
  6. Faculty of Chemistry, University of Wroc?aw, 50-383 Wroc?aw, Poland; The Joint Institute for Nuclear Research, Frank Laboratory of Neutron Physics, 141980 Dubna, Russia. Electronic address: [email protected].

PMID: 25965172 DOI: 10.1016/j.saa.2015.04.052

Abstract

Three β-hydroxynaphthylamides (morpholine, pyrrolidine and dimethylamine derivatives) have been synthesized and their conformational state was analyzed by NMR, X-ray and DFT calculations. In aprotic solution the molecules contain intramolecular OHO hydrogen bonds, which change into intermolecular ones in solid state. The energy barriers for the amide group rotation around the CN bond were estimated from the line shape analysis of (1)H and (13)C NMR signals. A tentative correlation between the barrier height and the strength of OHO bond was proposed. Calculations of the potential energy profiles for the rotations around CC and CN bonds were done. In case of morpholine derivative experimental indications of additional dynamics: chair-chair 'ring flip' in combination with the twisting around CC bond were obtained and confirmed by quantum chemistry calculations.

Copyright © 2015 Elsevier B.V. All rights reserved.

Keywords: Amide group rotation; Conformational isomerism; DNMR; Intramolecular hydrogen bond; Solvent effects; β-Hydroxynaphthylamides

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