Comparative analysis of theoretical and experimental UV-spectra of 2- and 8-thioquinoline
Автор: Matveychuk Yu.V., Ilkaeva M.V., Krivtsov I.V., Bartashevich E.V.
Журнал: Вестник Южно-Уральского государственного университета. Серия: Химия @vestnik-susu-chemistry
Рубрика: Физическая химия
Статья в выпуске: 2 т.7, 2015 года.
Бесплатный доступ
The comparative analysis of the calculated electronic absorption spectra of various forms of 2- and 8-thioquinoline and the experimental UV spectra of their solutions in various solvents has been carried out. Two conformational isomers of SH-forms have been analyzed for each compound. Calculations of other tautomeric forms of these compounds, namely NH-forms of 2-thioquinoline (2-thioquinolone) and 8-thioquinoline (zwitter-ion), and S-forms (anions) and 1-H-2-thioquinolinium cation have been analyzed additionally. It is shown that the absorption bands in the spectrum of 8-thioquinoline solution correspond to the electronic transitions in the SH-tautomer. On the contrary, the absorption bands in a spectrum of 2-thioquinoline solution correspond to the electronic transitions in the NH-tautomer and S-anion. The spreading of absorption bands in the experimental spectra is associated with conformational and tautomeric equilibrium which is established in the solutions of the considered compounds.
Thioquinoline, electronic absorption spectra, solvatochromic effect, td-dft
Короткий адрес: https://sciup.org/147160314
IDR: 147160314
Список литературы Comparative analysis of theoretical and experimental UV-spectra of 2- and 8-thioquinoline
- Chatterjee K.K. U.V. Absorption Spectra of 8-oxyquinoline and its Copper Chelate. Anal. Chim. Acta, 1959, vol. 20, pp. 232-235.
- Meislich H. Pyridinols and Pyridones, in: Klingsberg E. Pyridine and its Derivatives Pt. 3. NY London, Interscience Publishers, a division of John Wiley & Sons, 1962. pp. 619 630.
- Prabavathi N., Nilufer A., Krishnakumar V. Spectroscopic (FT-IR, FT-Raman, UV and NMR) Investigation, Conformational Stability, NLO Properties, HOMO-LUMO and NBO Analysis of Hydroxyquinoline Derivatives by Density Functional Theory Calculations. Spectrochim. Acta Pt. A: Mol. Biomol. Spectroscopy, 2013, vol. 114, pp. 449-474.
- Sharba A. H., Hassan H. A., Hassan D. F. Synthesis of Heterocyclic Compounds Derived from 2 Mercapto Quinoline. Ibn Al-Haitham J. Pure Appl. Sci., 2012, vol. 25, pp. 242-252.
- Obot I.B. Quantum Chemical Assessment of the Interaction of Potential Anticorrosion Additives with Steel Surface. Innov. Corr. Mater. Sci., 2014, vol. 4, pp. 107-117.
- Bartashevich E.V., Yushina I.D., Vershinina E.A., Slepukhin P.A., Kim D.G. Complex Structure Tri-and Polyiodides of Iodocyclization Products of 2-Allylthioquinoline. J. Struct. Chem., 2014, vol. 55, pp. 112 119.
- Kim D.G., Vershinina E.A. ChemInform Abstract: Synthesis and Properties of Thiazolo-and Oxazoloquinolinium Systems and Their Hydrogenated Derivatives (Review). ChemInform, 2015, vol. 46, in press.
- Chernov'yants M.S., Burykin I.V., Starikova Z.A., Tereznikov A.Yu., Kolesnikova T.S. Spectroscopic and Structural Study of Novel Interaction Product of Pyrrolidine-2-thione with Molecular Iodine. Presumable Mechanisms of Oxidation. J. Mol. Struct., 2013, vol. 1047, pp. 204-208.
- Chernov'yants M.S., Starikova Z.A., Karginova A.O., Kolesnikova T.S., Tereznikov A.Yu. Spectroscopic and Structural Investigation of Interaction Product of 8 Mercaptoquinoline with Molecular Iodine. Spectrochim. Acta Pt. A: Mol. Biomol. Spectroscopy, 2013, vol. 115, pp. 861-865.
- Runge E., Gross E. K. U. Density-Functional Theory for Time-Dependent Systems. Phys. Rev. Lett., 1984, vol. 52, pp. 997-1000.
- Dreuw A., Head-Gordon M. Single-Reference ab Initio Methods for the Calculation of Excited States of Large Molecules. Chem. Rev., 2005, vol. 105, pp. 4009-4037.
- Makarov A. Yu., Chulanova E.A., Semenov N.A., Pushkarevsky N.A., Lonchakov A.V., Bogomyakov A.S., Irtegova I.G., Vasilieva N.V., Lork E., Gritsan N.P., Konchenko S.N., Ovcharenko V.I., Zibarev A.V. A Novel Sulfur-Nitrogen -Heterocyclic Radical Anion, (6H-1,2,3 benzodithiazol-6-ylidene)malononitrilidyl, and its Homo-and Heterospin Salts. Polyhedron, 2014, vol. 72, pp. 43-49.
- Siud Pui Man, Benoit D.M., Buchaca E., Esan F., Motevalli M., Wilson J., Sullivan A. Synthesis, Structural Characterization, Experimental, and Computational Spectrophotometric Studies of 8-Quinolinyloxymethyphosphonate. Inorg.Chem., 2006, vol. 45, pp. 5328-5337.
- Karabacak M., Cinar M. FT-IR, FT-Raman, UV Spectra and DFT Calculations on Monomeric and Dimeric Structure of 2-Amino-5-bromobenzoic Acid. Spectrochim. Acta Pt. A: Mol. Biomol. Spectroscopy, 2012, vol. 86, pp. 590-599.
- Mennucci B., Tomasi J., Cammi R., Cheeseman J.R., Frisch M.J., Devlin F.J., Gabriel S., Stephens P.J. Polarizable Continuum Model (PCM) Calculations of Solvent Effects on Optical Rotations of Chiral Molecules. J. Phys. Chem. A, 2002, vol. 106, pp. 6102-6113.
- Tomasi J., Mennucci B., Cammi R. Quantum Mechanical Continuum Solvation Models. Chem. Rev., 2005, vol. 105, pp. 2999-3094.
- Jacquemin D., Perpète E.A., Ciofini I., Adamo C. On the TD-DFT UV/vis Spectra Accuracy: the Azoalkanes. Theor. Chem. Account, 2008, vol. 120, pp. 405-410.
- Adamo C., Barone V. Toward Reliable Density Functional Methods without Adjustable Parameters: The PBE0 Model. J. Chem. Phys., 1999, vol. 110, pp. 6158-6170.
- Becke A.D. Density-functional Thermochemistry. 3. The Role of Exact Exchange. J. Chem. Phys., 1993, vol. 98, pp. 5648-5652.
- Chengteh Lee, Weitao Yang, Parr R.G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density. Phys. Rev. B, 1988, vol. 37, pp. 785-789.
- Krishnan R., Binkley J. S., Seeger R., Pople J. A. Self-consistent Molecular Orbital Methods. XX. A Basis Set for Correlated Wave Functions. J. Chem. Phys., 1980, vol. 72, no. 1, pp. 650-654.
- McLean A. D., Chandler G. S. Contracted Gaussian Basis Sets for Molecular Calculations. I. Second Row Atoms, Z=11-18. J. Chem. Phys., 1980, vol. 72, no. 10, pp. 5639-5648.
- Emsley John. The Elements (3rd Ed.). Oxford, Oxford University Press, 1998. 300 p.
- Granovsky A.A. Firefly version 8. Available at: http://classic.chem.msu.su/gran/firefly/index.html (accessed 28 February 2015).
- Reichardt C. Solvents and Solvent Effects in Organic Chemistry (2nd Ed.). Weinheim, VCH Verlagsgesellschaft mbH, D-6940, 1988. 750 p.
- Feher P.P., Purgel M., Joo F. Performance of Exchange-Correlation Functionals on Describing Ground State Geometries and Excitations of Alizarin Red S: Effect of Complexation and Degree of Deprotonation. Comput. Theor. Chem., 2014, vol. 1045, pp. 113-122.
