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2003 | 1 | 4 | 427-440
Tytuł artykułu

Thermally induced oxidative trimerization of benzimidazole by copper(II) chloride in the solid state

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Benzimidazolium trichlorocuprate(II) undergoes a redox reaction in the solid state at elevated temperature (∼240°C) to produce the cyclic trimer of benzimidazole and cuprous chloride. The trimer has been characterized by IR, NMR, and Mass spectroscopy. It has also been synthesized in lower yield by heating the mixtures of CuCl2 and benzimidazole in different ratios or heating other compounds of CuCl2 and benzimidazole. The absorption, emission, and excitation spectra of the trimer in two different solvents (TFA and DMSO) and a comparison of these results with those of benzimidazole are presented here.
Wydawca

Czasopismo
Rocznik
Tom
1
Numer
4
Strony
427-440
Opis fizyczny
Daty
wydano
2003-12-01
online
2003-12-01
Twórcy
  • Department of Chemistry, University College of Science and Technology, University of Calcutta, 92, A. P. C. Road, 700 009, Kolkata, India, ghosh_59@yahoo.com
autor
  • Department of Chemistry, University College of Science and Technology, University of Calcutta, 92, A. P. C. Road, 700 009, Kolkata, India
autor
  • Department of Chemistry, B. E. College (D.U.), 711 103, Botanic Garden, Howrah, India
  • Department of Chemistry, University College of Science and Technology, University of Calcutta, 92, A. P. C. Road, 700 009, Kolkata, India
Bibliografia
  • [1] A.R. Katritzky, and C.W. Rees: Comprehensive Heterocyclic, Chemistry, Vol. 5.
  • [2] E.R. Cole, G. Crank, and E. Lye: “Photochemistry of Heterocyclics. II Photolysis of Benzimidazole and its 2-Alkyl Derivatives”, Aust. J. Chem., Vol. 31, (1978), pp. 2675–2684. http://dx.doi.org/10.1071/CH9782675[Crossref]
  • [3] W.E. Haines, R.V. Helm, J.L. Cook, and J.S. Ball: “Purification and Properties of Ten Organic Sulfur Compounds-Second Series”, J. Phys. Chem., Vol. 60, (1956), pp. 549–555. http://dx.doi.org/10.1021/j150539a009[Crossref]
  • [4] K.H. Grellmann, and E. Tauer: “Symmetric photodehydrodimerizations formation of 2,2/dibenzoxazole and 2,2/dibenzthiazole”, Tetrahedron Lett., (1974), pp. 375–376. [Crossref]
  • [5] S. Ishida, Y. Fukushima, S. Sekiguchi, and K. Matsui: “Tris(benzimidazo)-1,3,5-triazine from the thermolysis of 2-aryloxybenzimidazoles”, Bull. Chem. Soc. Japan, Vol. 48(3), (1975), pp. 956–959. http://dx.doi.org/10.1246/bcsj.48.956[Crossref]
  • [6] D. Martin and F. Tittelbach: “Exchange, elimination, and ring opening reactions of 3-dihydrobenzimidazo[1,2-d][1,2,4]thiadiazoles and 3H-benzimidazo[2,1-c][1,2,4]dithiazoles”, J. Chem. Soc. Perkin Trans I, Vol. 5, (1985), pp. 1007–1013. http://dx.doi.org/10.1039/p19850001007[Crossref]
  • [7] G.I. Gofen, C.S. Kadyrov, M.N. Kosyakovskaya: “Cyclic trimer of benzimidazole”, Khim. Geterots. Soed., Vol. 7(2), (1971), pp. 282.
  • [8] W. Kuzmierkiewicz: “Oxidation reaction of benzimidazoline-2-thione with dimethyl sulfoxide”, Pol. J. Chem., Vol. 59(7–9), (1985), pp. 921–923.
  • [9] E.R. Lavagnino, D.C. Thompson: “Trimerization of 2-chloro-, 2-hydroxy-, and 2-mercaptobenzimidazoles”, J. Heterocycl. Chem., Vol. 9(1), (1972), pp. 149–150. http://dx.doi.org/10.1002/jhet.5570090127[Crossref]
  • [10] R. Bhattacharya, M.S. Ray, R. Dey, L. Righi, G. Bocelli, and A. Ghosh: “Synthesis, crystal structure and thermochromism of benzimidazolium tetrachlorocuprate: (C7H7N2)2[CuCl4]”, Polyhedron, Vol. 21, (2002), pp. 2561–2565. http://dx.doi.org/10.1016/S0277-5387(02)01237-8[Crossref]
  • [11] T.C. Wong, J. Kovac, C.S. Lee, L.S. Hung, and S.T. Lee: “Transient electroluminescence measurements on electron mobility of N-arylbenzimidazoles”, Chem. Phys. Lett., Vol. 334, (2001), pp. 61–64. http://dx.doi.org/10.1016/S0009-2614(00)01442-1[Crossref]
  • [12] G. Berden, W. Leo Meerts, and E. Jalvista: “Rotatioally resolved ultraviolet spectroscopy of indole, indazole, and benzimidazole: Inertial axis reorientation in the S1(1Lb )←S0 transitions”, J. Chem. Phys., Vol. 103, (1995), pp. 9596–9606. http://dx.doi.org/10.1063/1.469974
  • [13] S. Santra, G. Krishnamoorthy, and S.K. Dogra: “Spectral characteristics of the methylated derivatives of 2-(2/-aminophenyl)benzimidazole: effects of solvents”, J. Mol. Str, Vol. 559, (2001), pp. 25–39. http://dx.doi.org/10.1016/S0022-2860(00)00684-0[Crossref]
  • [14] A. I. Vogel: A Text book of Quantitative Inorganic Analysis, 4th edition, Longman, New York, 1978.
  • [15] B.N. Figgis and J. Lewis: Modern Coordination Chemistry, ed. J. Lewis, and R.C. Wilkins, Interscience, New York, 1960, p.-403.
  • [16] M. Bukowska-Strzyzewska, and J. Skoweranda: “Structure of Thermochromic Crystals of Benzimidazolium Tetrachlorocuprate(II) Hydrate”, Acta. Cryst., Vol. C 43, (1987), pp. 2290–2293.
  • [17] M.C. Ball, and R.F.M. Coultard: “Thermal Studies on Halides and Basic Halides of Copper(II)”, J. Chem. Soc., 1968A, pp. 1417–1419. [Crossref]
  • [18] J.K. Dey and S.K. Dogra: “Dual Fluorescence of 2-[4-(Dimethylamino)phenyl] benzothiazole and Its Benzimidazole Analog: Effect of Solvent and pH on Electronic Spectra”, J. Phys. Chem., Vol. 98, (1994), pp. 3638–3644. http://dx.doi.org/10.1021/j100065a016[Crossref]
  • [19] M. Krishnamurthy, P. Phaniraj, and S.K. Dogra: “Absorptiometric and Fluorometric Study of Solvent Dependence and Prototropism of Benzimidazole Homologues”, J. Chem. Soc. Perkin Trans II, (1986), pp. 1917–1925.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02475226
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