OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS
Is it possible to differentiate between 2-phenylaminodihydro-1,3-thiazine from 2-phenyliminotetrahydro-1,3-thiazine by spectral methods? New glance to the old problem
Alisher Eshimbetov (1) , Shahobiddin Adizov (2,*) , Inderpreet Kaur (3) , Akhmed Reymov (4)
(1) Laboratory of Complex Compounds, Institute of Bioorganic Chemistry, Academy of Sciences of the Republic of Uzbekistan, Mirzo Ulugbek Street 83, Tashkent, 100125, Uzbekistan
(2) Laboratory of High-Molecular Plant Substances, Institute of The Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, 100170, Uzbekistan
(3) Department of Ubiquitous Analytical Techniques, Central Scientific Instruments Organization, Chandigarh, 160030, India
(4) Faculty of Chemical-Technology, Karakalpak State University, Nukus, 230112, Uzbekistan
(*) Corresponding Author
Received: 14 Jan 2021 | Revised: 18 Feb 2021 | Accepted: 20 Feb 2021 | Published: 31 Mar 2021 | Issue Date: March 2021
Several studies have reported the presence of amine and imine tautomeric forms for hydrogenated 1,3-thiazine derivatives. However, identification of their tautomeric forms by UV, FTIR and mass-spectral methods does not yield expected results. Here, we report the synthesis of 2-phenylaminodihydro-1,3-thiazine and 2-phenyliminotetrahydro-1,3-thiazine and the analysis of their UV, FTIR and NMR (1H and 13C) spectral data. An identical picture of UV spectra was recorded for both compounds. However, distinctive characteristics were found in the FTIR, 1H and 13C NMR spectra. The C=N band of amine form was observed in higher frequency region relative to imine form. The signal of C2 carbon of amine form in 13C NMR spectrum was occurred in more downfield (δ 165.3 ppm) relative to C2 signal of imine form (δ 152.1 ppm). In addition, the difference between C2 and C8 carbon signals of amine form was very high (Δδ = 30.6 ppm) relative to imine form (δ 5.4 ppm). The position of C2 and C8 signals and the difference between them in 13C NMR spectrum was found to be more promising in identification of tautomeric forms in case of hydrogenated 1,3-thiazine derivatives.
Links for Article
| | | | | | |
| | | | | | |
| | |
Article MetricsThis Abstract was viewed 60 times | PDF Article downloaded 22 times
Institute of The Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, 100170, Uzbekistan.
. Toldy, L. G. Chem. Heterocycl. Compd. 1978, 14 (7), 705-714.
. Tisler, M. Arch. Pharm. Pharm. Med. Chem. 1960, 293 (6), 621-626.
. Engoyan, A. P.; Peresleni, E. M.; Sheinker, Yu. N.; Ignatova, L. A.; Unkovskii, B. V. Chem. Heterocycl. Compd. 1976, 12 (8), 866-868.
. Jackman, L. M.; Jen, T. J. Am. Chem. Soc. 1975, 97 (10), 2811-2818.
. Toth, G.; Almasy, A. Org. Magn. Reson. 1982, 19 (4), 219-221.
. Kalman, A.; Argay, G.; Ribar, B.; Toldy, L. Tetrahedron Lett. 1977, 18 (48), 4241-4244.
. Remko, M.; Walsh, O. A.; Richards, W. G. Chem. Phys. Lett. 2001, 336 (1-2), 156-162.
. Muir, W.; Hubbell, J. A. Handbook of Veterinary Anesthesia, 5th edition, ISBN: 9780323080699, Elsevier Inc, 2014.
. Gnanasekaran, K.; Hiett, J.; Bunce, R. Molbank 2016, 2016 (2), M899
. Li, Y.; Kong, S.; Yang, F.; Xu, W. Int. J. Mol. Sci. 2018, 19 (5), 1530, 1-15.
. Thanusu, J.; Kanagarajan, V.; Gopalakrishnan, M. J. Enzyme Inh. Med. Chem. 2010, 25 (6), 756-764.
. Proskuryakov, S. Ya.; Filimonova, M. V.; Verkhovskii, Yu. G.; Konoplyannikov, A. G.; Mandrugin, A. A.; Fedoseev, V. M.; Skvortsov, V. G. Bull. Exp. Biol. Med. 2004, 138 (4), 397-400.
. Trofimova, T. P.; Zefirova, O. N.; Mandrugin, A. A.; Fedoseev, V. M.; Peregud, D. I.; Onufriev, M. V.; Gulyaeva, N. V.; Proskuryakov, S. Y. Moscow Univ. Chem. Bull. 2008, 63 (5), 274-277.
. Badshah, S.; Naeem, A. Molecules 2016, 21 (8), 1054, 1-20.
. Dardonville, C.; Nue Martinez, J. J. Curr. Med. Chem. 2017, 24 (33), 3606-3632.
. Kai, H.; Morioka, Y.; Murashi, T.; Morita, K.; Shinonome, S.; Nakazato, H.; Kawamoto, K.; Hanasaki, K.; Takahashi, F.; Mihara, S.; Arai, T.; Abe, K.; Okabe, H.; Baba, T.; Yoshikawa, T.; Takenaka, H. Bioorg. Med. Chem. Lett. 2007, 17 (14), 4030-4034.
. Corbett, M.; Caille, S. Synlett. 2017, 28 (20), 2845-2850.
. Eshimbetov, A. G.; Kaur. I. Synthesis of 1-(2-hydroxyethyl, 3-hydroxypropyl and 4-hydroxybutyl)-3-phenylthiourea and their spectral properties. Conference proceedings, Problems of Bioorg. Chem. IX. Youth Chemists Republican Conference, Vol. 1, P. 10, Namangan, Uzbekistan, April 26-27, 2019.
. Rabinowitz, J.; Chang, S.; Hayes, J. M.; Woeller, F. J. Org. Chem. 1969, 34 (2), 372-376.
. Smith, B. C. Fundamentals of Fourier Transform Infrared Spectroscopy, 2nd Edition CRC Press, ISBN 9781420069297, Boca Raton, Florida, 2011.
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.12.1.77-80.2068
| | | | | | | | |
| | | | | |
Save to Zotero Save to Mendeley
European Journal of Chemistry 2021, 12(1), 77-80 | doi: https://doi.org/10.5155/eurjchem.12.1.77-80.2068 | Get rights and content
- There are currently no refbacks.
Copyright (c) 2021 Authors
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).
© Copyright 2010 - 2021 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2021 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.