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Theoretical investigation on tautomerism and NBO analysis of 3-hydroxy-1,2,5-thiadiazole derivatives: solvent and substituent effects

  • Meisam Shabanian EMAIL logo , Mohsen Hajibeygi , Hassan Moghanian and Azin Mohamadi
Published/Copyright: August 1, 2012
Heterocyclic Communications
From the journal Heterocyclic Communications Volume 18 Issue 3

Abstract

Thiadiazole compounds including 3-hydroxy-4-substituted-1,2,5-thiadiazole are known as non-nucleoside inhibitors of HIV-1. Density functional calculations at the B3LYP/6-311++G(d,p) level were employed to determine the stability, tautomerism, and substituent effects of 1,2,5-thiadiazole, a widely used skin-whitening, antibrowning, and antibacterial agent, and its derivatives (4-NO2, 4-CN, 4-F, 4-H, 4-Me, 4-NH2), in the gas phase and solution using the polarizable continuum method model. Some selected IR frequencies, molecular parameters, charges on atoms, and dipole moment results were analyzed.

Keywords: DFT study; NBO analysis; solvent effect; tautomerism; 1,2,5-thiadiazole
Corresponding author: Meisam Shabanian, Young Researchers Club, Arak Branch, Islamic Azad University, Arak, Iran.

References

Ahn, D. S.; Lee, S.; Bongsoo, K. Solvent-mediated tautomerization of purine: single to quadruple proton transfer. Chem. Phys. Lett. 2004, 390, 384–388.10.1016/j.cplett.2004.03.152Search in Google Scholar

Angelova, S.; Enchev, V. Ab initio study of 2,4-substituted azolidines. I. Tautomerism. J. Mol. Struct. THEOCHEM. 2004, 711, 201–207.10.1016/j.theochem.2004.09.022Search in Google Scholar

Barone, V.; Cossi, M.; Tomasi, J. Geometry optimization of molecular structures in solution by the polarizable continuum model. J. Comp. Chem. 1998, 19, 404–417.10.1002/(SICI)1096-987X(199803)19:4<404::AID-JCC3>3.0.CO;2-WSearch in Google Scholar

Cossi, M.; Barone, V.; Mennucci, B.; Tomasi, J. Ab initio study of ionic solutions by a polarizable continuum dielectric model. Chem. Phys. Lett. 1998, 286, 253–260.10.1016/S0009-2614(98)00106-7Search in Google Scholar

Dennington, R.; Keith, T.; Millam, J.; Eppinnett, K.; Hovell, W. L.; Gilliland, R. GaussView, Version 309, Semichem, Inc.: Shawnee Mission, KS, 2003.Search in Google Scholar

Dines, T. J.; Onoh, H. An infrared and resonance Raman spectroscopic study of phenylazonaphthol pigments. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2006, 64, 891–900.10.1016/j.saa.2005.08.019Search in Google Scholar

Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; et al. Gaussian 03, Revision B.03, Gaussian, Inc.: Pittsburgh, PA, 2003.Search in Google Scholar

Grochowski, J.; Serda, P.; Kozik, B. Structural and energetic characterization of ylidenemalonodinitrile tautomers, precursors of fungicidal species. J. Mol. Struct. THEOCHEM. 2004, 689, 43–48.10.1016/j.molstruc.2003.10.021Search in Google Scholar

Hanasaki, Y.; Watanabe, H.; Katsuura, K.; Takayama, H.; Shirakawa, S.; Yamaguchi, K.; Sakai, Sh.; Ijichi, K.; Fujiwara, M.; Konno, K.; et al. Thiadiazole derivatives: highly potent and specific HIV-1 reverse transcriptase inhibitors. J. Med. Chem. 1995, 38, 2038–2040.10.1021/jm00012a002Search in Google Scholar

Hasanein, A.; Senior, S. A. DFT calculations of amine-imine tautomerism in some pyrimidine derivatives and their 1:1 and 1:2 complexes with water. Int. J. Quantum Chem. 2011, 111, 3993–4010.10.1002/qua.22739Search in Google Scholar

Hocquet, A.; Toro-Labbé, A.; Chermette, H. Intramolecular interactions along the reaction path of keto-enol tautomerism: Fukui functions as local softnesses and charges as local hardnesses. J. Mol. Struct. THEOCHEM. 2004, 686, 213–218.10.1016/j.theochem.2004.08.011Search in Google Scholar

Kayukova, L. A.; Praliev, K. D.; Zhumadildaeva, I. S.; Klepikova, S. G. Unexpectedly facile heterocyclization of o-benzoyl-β-piperidino-propioamidoxime in dimethyl sulfoxide. Chem. Heterocycl. Comp. 1999, 35, 630–631.10.1007/BF02324652Search in Google Scholar

Kleinpeter, E.; Koch, A. Tautomerism in 4-substituted 1-phenyl-3-methyl-pyrazolin-5-ones – a theoretical ab initio and 13C NMR study. J. Phys. Org. Chem. 2001, 14, 566–576.10.1002/poc.412Search in Google Scholar

Koch, A.; Kleinpeter, E. Study of the tautomerism by experimentally and theoretically estimated 13C and 15N chemical shifts. J. Mol. Model. 1997, 3, 375–381.10.1007/s008940050054Search in Google Scholar

Mamdouh, M. A.; Sohair, A. H. Role of some newly synthesized tetrahydronaphthalenthiazol derivatives as anticancer compounds. Int. J. Cancer Res. 2007, 3, 103–110.10.3923/ijcr.2007.103.110Search in Google Scholar

Miertus, S.; Scrocco, E.; Tomasi, J. Electrostatic interaction of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects. Chem. Phys. 1981, 55, 117–129.10.1016/0301-0104(81)85090-2Search in Google Scholar

Minkin, V. I.; Garnovski, A. D.; Elguero, J.; Katritzky, A. R.; Denisko, O. The tautomerism of heterocycles: five-membered rings with two or more heteroatoms. Adv. Heterocycl. Chem. 2000, 76, 157–323.10.1016/S0065-2725(00)76005-3Search in Google Scholar

Mishra, G.; Singh, A. K.; Jyoti, K. Review article on 1,3,4-thiadiazole derivatives and its pharmacological activities. Int. J. Chem. Tech. Res. 2011, 3, 1380–1393.Search in Google Scholar

Najafi Chermahini, A.; Nasr-Esfahani, M.; Dalirnasab, Z.; Abdol Dabbagh, H.; Teimouri, A. Theoretical studies on tautomerism of tetrazole derivatives by polarisable continuum method (PCM). J. Mol. Struct. THEOCHEM. 2007, 820, 7–11.10.1016/j.theochem.2007.05.043Search in Google Scholar

Sauerberg, P.; Jeppesen, L.; Olesen, P. H.; Rasmussen, T.; Swedberg, M. D.; Sheardown, M. J.; Fink-Jensen, A.; Thomsen, C.; Thøgersen, H.; Rimvall, K.; et al. Muscarinic agonists with antipsychotic-like activity: structure-activity relationships of 1,2,5-thiadiazole analogues with functional dopamine antagonist activity. J. Med. Chem. 1998, 41, 4378–4384.10.1021/jm981048eSearch in Google Scholar PubMed

Shabanian, M.; Moghanian, H.; Hajibeygi, M.; Mohamadi, A. A DFT study of solvation effects and NBO analysis on the tautomerism of 1-substituted hydantoin. Arabian J. Chem. 2011, Doi:10.1016/j.arabjc.2011.08.014.10.1016/j.arabjc.2011.08.014Search in Google Scholar

Swamy, S. N.; Basappa; Priya, B. S.; Prabhuswamy, B.; Doreswamy, B. H.; Prasad, J. S.; Rangappa, K. S. Synthesis of pharmaceutically important condensed heterocyclic 4,6-disubstituted-1,2,4-triazolo-1,3,4-thiadiazole acid. Eur. J. Med. Chem. 2008, 5, 963–968.Search in Google Scholar

Tavakol, H.; Esfandyari, M.; Taheri, S.; Heydari, A. Investigation of structure, vibrational and NMR spectra of oxycodone and naltrexone: a combined experimental and theoretical study. Spectrochim. Acta A, Mol. Biomol. Spectrosc. 2011, 79, 574–582.10.1016/j.saa.2011.03.038Search in Google Scholar PubMed

Weinstock, L. M.; Davis, P.; Handelsman, B.; Tull, R. A. General synthetic system for 1,2,5-thiadiazoles. J. Org. Chem. 1967, 32, 2823–2829.10.1021/jo01284a040Search in Google Scholar

Zborowski, K.; Korenova, A. Quantum chemical studies on tautomeric equilibria in chlorokojic and azidokojic acids. J. Mol. Struct. THEOCHEM. 2004, 683, 15–22.10.1016/j.theochem.2004.06.007Search in Google Scholar
Received: 2011-11-23
Accepted: 2012-01-10
Published Online: 2012-08-01
Published in Print: 2012-08-01

©2012 Walter de Gruyter GmbH & Co. KG, Berlin/Boston

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  1. Supplementary data
  2. Masthead
  3. Masthead
  4. Preliminary Communications
  5. Synthesis and molecular structure of (Z)-1H-purin-6-ylideneaminooxysulfonic acid: a possible secondary metabolite of adenine
  6. Design and synthesis of heterocyclic enamine derivatives based on skeleton of neonicotinoids
  7. Research Articles
  8. Reductive amination of 6-acetylpteridine to 6-N-arylaminoethylpteridine
  9. Efficient synthesis of selected phthalazine derivatives
  10. Synthesis of novel fluorescent 1,3,5-trisubstituted triazine derivatives and photophysical property evaluation of fluorophores and their BSA conjugates
  11. Fast and efficient microwave synthetic methods for some new 2(1H)-pyridone arabinosides
  12. Simple and efficient synthesis of novel N-dichloroacetyl-3,4-dihydro-2H-1,4-benzoxazines
  13. Palladium-catalyzed cascade reactions of benzyl halides with N,N-diallyl-p-toluenesulfonamide
  14. Iodine-catalyzed synthesis of 5-arylanthra[2,1-c][2,7]naphthyridine derivatives via three-component reaction
  15. One-pot synthesis of acenaphtho[1,2-b]pyrroles in the presence of supported ionic liquid catalyst
  16. Theoretical investigation on tautomerism and NBO analysis of 3-hydroxy-1,2,5-thiadiazole derivatives: solvent and substituent effects
https://doi.org/10.1515/hc-2011-0121
Keywords for this article
DFT study; NBO analysis; solvent effect; tautomerism; 1,2,5-thiadiazole

Articles in the same Issue

  1. Supplementary data
  2. Masthead
  3. Masthead
  4. Preliminary Communications
  5. Synthesis and molecular structure of (Z)-1H-purin-6-ylideneaminooxysulfonic acid: a possible secondary metabolite of adenine
  6. Design and synthesis of heterocyclic enamine derivatives based on skeleton of neonicotinoids
  7. Research Articles
  8. Reductive amination of 6-acetylpteridine to 6-N-arylaminoethylpteridine
  9. Efficient synthesis of selected phthalazine derivatives
  10. Synthesis of novel fluorescent 1,3,5-trisubstituted triazine derivatives and photophysical property evaluation of fluorophores and their BSA conjugates
  11. Fast and efficient microwave synthetic methods for some new 2(1H)-pyridone arabinosides
  12. Simple and efficient synthesis of novel N-dichloroacetyl-3,4-dihydro-2H-1,4-benzoxazines
  13. Palladium-catalyzed cascade reactions of benzyl halides with N,N-diallyl-p-toluenesulfonamide
  14. Iodine-catalyzed synthesis of 5-arylanthra[2,1-c][2,7]naphthyridine derivatives via three-component reaction
  15. One-pot synthesis of acenaphtho[1,2-b]pyrroles in the presence of supported ionic liquid catalyst
  16. Theoretical investigation on tautomerism and NBO analysis of 3-hydroxy-1,2,5-thiadiazole derivatives: solvent and substituent effects
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