Combined approach to UV-Vis study of 2-allyl and 2-ethylthioquinolines in various solutions

Автор: Matveychuk Yu.V., Ilkaeva M.V., Vershinina E.A., Batalov V.I., Bartashevich E.V.

Журнал: Вестник Южно-Уральского государственного университета. Серия: Химия @vestnik-susu-chemistry

Рубрика: Физическая химия

Статья в выпуске: 1 т.8, 2016 года.

Бесплатный доступ

Combined approach to analysis of 2-allylthioquinoline and 2-ethylthioquinoline solutions has been performed on the basis of UV-Vis spectroscopy. Experimental and calculated electronic absorption spectra of these compounds in various solvents: acetone, benzene, carbon tetrachloride, dichloromethane, ethanol have been considered. The negative solvatochromic effect has been observed. The results of our calculations have revealed that the spectra of various conformers of 2-allylthioquinoline differ more essentially than the spectra of 2-ethylthioquinoline conformers. It has been shown that the location of λ max band doesn’t drastically depend on allyl or alkyl substitution at the sulfur atom.

Еще

Electronic absorption spectra, substituted 2-thioquinolines, solvatochromic effect, td dft calculation, td dft расчёты

Короткий адрес: https://sciup.org/147160342

IDR: 147160342   |   DOI: 10.14529/chem160105

Список литературы Combined approach to UV-Vis study of 2-allyl and 2-ethylthioquinolines in various solutions

  • Runge E., Gross E.K.U. Density-Functional Theory for Time-Dependent Systems. Physical Review Letters, 1984, vol. 52, pp. 997-1000. DOI: DOI: 10.1103/PhysRevLett.52.997
  • Dreuw A., Head-Gordon M. Single-Reference ab Initio Methods for the Calculation of Excited States of Large Molecules. Chemical Reviews, 2005, vol. 105, pp. 4009-4037. DOI: DOI: 10.1021/cr0505627
  • Jacquemin D., Perpète E.A., Ciofini I., Adamo C. On the TD-DFT UV/Vis Spectra Accuracy: the Azoalkanes. Theoretical Chemistry Accounts, 2008, vol. 120, pp. 405-410. DOI: DOI: 10.1007/s00214-008-0424-9
  • 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 π-heterocyclic Radical Anion, (6H-1,2,3-benzodithiazol-6-ylidene)malononitrilidyl, and its Homo-and Heterospin Salts. Polyhedron, 2014, vol. 72, pp. 43-49. DOI: DOI: 10.1016/j.poly.2014.01.027
  • Siud Pui Man, Benoit D.M., Buchaca E., Fola Esan, Motevalli M., Wilson J., Sullivan A. Synthesis, Structural Characterization, Experimental, and Computational Spectrophotometric Studies of 8-Quinolinyloxymethyphosphonate Compounds. Inorganic Chemistry, 2006, vol. 45, pp. 5328-5337. DOI: DOI: 10.1021/ic052085g
  • Becke A.D. Density-functional Thermochemistry. III. The Role of Exact Exchange. The Journal of Chemical Physics, 1993, vol. 98, pp. 5648-5652. DOI: DOI: 10.1063/1.464913
  • Lee C., Yang W., Parr R.G. Development of the Colle-Salvetti Correlation-energy Formula into a Functional of the Electron Density. Physical Review B, 1988, vol. 37, pp. 785-789. DOI: DOI: 10.1103/PhysRevB.37.785
  • Krishnan R., Binkley J.S., Seeger R., Pople J.A. Self-consistent Molecular Orbital Methods. XX. A Basis Set for Correlated Wave Functions. The Journal of Chemical Physics, 1980, vol. 72, No. 1, pp. 650-654. DOI: DOI: 10.1063/1.438955
  • McLean A.D., Chandler G.S. Contracted Gaussian Basis Sets for Molecular Calculations. I. Second Row Atoms, Z=11-18. The Journal of Chemical Physics, 1980, vol. 72, No. 10, pp. 5639-5648. DOI: DOI: 10.1063/1.438980
  • Klamt A. Calculation of UV/Vis Spectra in Solution. The Journal of Physical Chemistry, 1996, vol. 100, pp. 3349-3353. DOI: DOI: 10.1021/jp950607f
  • 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. The Journal of Physical Chemistry A, 2002, vol. 106, pp. 6102-6113 DOI: 10.1021/jp020124t
  • Tomasi J., Mennucci B., Cammi R. Quantum Mechanical Continuum Solvation Models. Chemical Reviews, 2005, vol. 105, pp. 2999 3094 DOI: 10.1021/cr9904009
  • Karabacak M., Cinar M. FT-IR, FT-Raman, UV Spectra and DFT Calculations on Monomeric and Dimeric Structure of 2-Amino-5-bromobenzoic Acid. Spectrochimica Acta A, 2012, vol. 86, pp. 590-599 DOI: 10.1016/j.saa.2011.11.022
  • Kim D.G. Synthesis and Halocyclization of 2-Alkenylthioquinolines. Chemistry of Heterocyclic Compounds, 2008, vol. 44, pp. 1355-1358 DOI: 10.1007/s10593-009-0195-9
  • Kim D.G., Vershinina E. A. Synthesis of the Thiazoloquinolinium System. Chemistry of Heterocyclic Compounds, 2010, vol. 46, pp. 773-774 DOI: 10.1007/s10593-010-0585-z
  • Bremond E., Kieffer J., Adamo C. A Reliable Method for Ftting TD DFT Transitions to Experimental UV-visible Spectra. Journal of Molecular Structure: THEOCHEM, 2010, vol. 954, pp. 52 56 DOI: 10.1016/j.theochem.2010.04.038
  • Bremond E., Le Bahersc T., Riccid G., Ciofinia I., Adamo C. In Silico Assessment of the HPLC-UV Response Coefficients. Computational and Theoretical Chemistry, 2014, vol. 1040-1041, pp. 1 5 DOI: 10.1016/j.comptc.2014.03.028
  • Adamo C., Barone V. Toward Reliable Density Functional Methods without Adjustable Parameters: The PBE0 Model. The Journal of Chemical Physics, 1999, vol. 110, pp. 6158-6170 DOI: 10.1063/1.478522
  • Matveychuk Yu. V., Ilkaeva M.V., Krivtsov I.V., Bartashevich E.V. Comparative Analysis of Theoretical and Experimental UV-Spectra of 2-and 8-Thioquinoline. Bulletin of the South Ural State University. Ser. Chemistry, 2015, vol. 7, No. 2, pp. 45-55.
  • Emsley J. 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 2 January 2016).
  • Andrienko G.A. Chemcraft v.1.6. Available at: http://www.chemcraftprog.com/index.html (accessed 2 January 2016).
  • Reichardt C. Solvents and Solvent Effects in Organic Chemistry (2nd Ed.). Weinheim, VCH Verlagsgesellschaft mbH, D-6940, 1988. 750 p.
Еще
Статья научная