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