Acid-base and spectral properties of 3 (benzothiazolyl-2)cumarins and their imino analogs

  • Z. A. Sizova V.N. Karazin Kharkiv National University
  • Alexander A. Karasyov PreSens Precision Sensing GmbH
  • L. L. Lukackaya State Institution Danilevskii Institute for Endocrine Pathology Problems, National Academy of Medical Sciences of Ukraine
  • Andrey O. Doroshenko V.N. Karazin Kharkiv National University https://orcid.org/0000-0002-9643-9549
Keywords: iminochromens, cumarins, protolytic equilibria, hydrolysis, tautomerizm

Abstract

Systematic series of 3-(benzothiazolyl-2)coumarin derivatives and their imino analogs were synthesized. Spectral-luminescent properties in acetonitrile solutions, acid-base equilibria in water-alcohol media, reaction of imino-group hydrolysis were investigated for the title compounds. Tautomerism of 7-hydroxy-2-iminochromens in water-alcohol solutions and possibility of practical application of 7-methoxycumarin as fluorescence quantum yield reference compound are discussed as well.

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References

Krasovitskiy B.M., Bolotin B.M. Organic Luminescent Materials. VCH Verlagsgesellschaft mbH, Weinheim, 1988. 340 p.

Dye Lasers. (Ed. F.P. Schafer). Berlin-Heidelberg - New York, Springer-Verlag, 1973, 285 p.

Raue R., Harnisch H., Drexhage K.H. // Heterocycles. 1984. Vol. 21. № 1. P. 167–190.

Lakowicz J. Principles of fluorescence spectroscopy, 2nd Ed. New York: Kluwer Acad./ Ple-num Publ., 1999. 698 p.

DeLisser-Matthews L.A., Kauffman J.M. // Analyst. 1984. Vol. 109. № 8. P. 1009–1011.

Wolfbeis O.S., Baustert J.H. // J. Heterocycliс Chem. 1985. Vol. 22. P. 1215–1218.

Wolfbeis O.S., Marhold H. // Fresenius Z. Anal. Chem. 1987. Vol. 327. P. 347–350.

Dong S., Ma H., Li H., Sun M., Duan X. // Analytical Letters. 2004. Vol. 37. № 14. P. 2937 2948.

Vasylevska G.S., Karasyov A.A., Borisov S.M., Krause Ch. // Anal. Bioanal. Chem. 2007. Vol. 387. P. 2131–2141.

O'Callaghan C.N., McMurry T.B.H., Cardin C.J. // J. Chem. Res. (S). 1990. № 5. P. 132–133; J. Chem. Res. (M). 1990. № 5. P. 901–922.

Karasyov A.A, Lukatskaya L.L., Rubtsov M.I., Zhikol E.K., Yarmolenko S.N., and Po-nomarev O.A., Zh. Obshch. Khim., 1995. Vol. 65. P. 1547–1557.

Dryanska V. // Synth. Commun. 1987. Vol. 17. № 2. P. 203–209.

Syzova Z.A., Karasyov A.A, Lukatskaya L.L., Rubtsov M.I., Doroshenko A.O. // Theoretical and Experimental Chemistry. 2002. Vol. 38. № 3. P. 168-172.

Ponomarev O.A., Vasina E.R., Yarmolenko S.N., Mitina V.G. // Zhurnal Obshchei Khimii. 1985. Vol. 55. № 1. P. 179–183.

J.J.P. Stewart. MOPAC 2012, Stewart computational Chemistry Ver. 13.238w, http://openmopac.net.

Maia J.D.C., Carvalho G.A.U., Mangueira C.P.,. Santana Jr., S.R, Cabral L.A.F., Rocha G.B.. GPU Linear Algebra Libraries and GPGPU Programming for Accelerating MOPAC Semiem-pirical Quantum Chemistry Calculations // J. Chem. Theory Comput. 2012. Vol. 8, P. 3072 3081.

Parker C.A. Photoluminescence of solutions. Elsevier Publishing Co., Amsterdam-London-New York 1968. 544 p.

Davis C.W. Ion Association. London. Butterworths, 1962. 190 p.

Swinbourne E.S. // J. Chem. Soc. 1960. № 5. P. 2371.

Bugaevskii A.A., Kholin Yu.V., Konyaev D.S. Computer calculation of complex formation constants from spectrophotometric data // Russian J. of Inorganic Chemistry. 1993. – V. 38, No 2. – P. 328-334.

Published
2016-05-05
Cited
How to Cite
Sizova, Z. A., Karasyov, A. A., Lukackaya, L. L., & Doroshenko, A. O. (2016). Acid-base and spectral properties of 3 (benzothiazolyl-2)cumarins and their imino analogs. Kharkiv University Bulletin. Chemical Series, (26), 26-38. https://doi.org/10.26565/2220-637X-2016-26-03

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