Study of Electrochemical Behaviour of Some 2,5-Dihydro-1,3,4-thiadiazoles

Turowska, M.; G. Mlostoń, G.; M. Celeda, M.; J. Raczak, J.

Artykuł - szczegóły

Tytuł artykułu

Study of Electrochemical Behaviour of Some 2,5-Dihydro-1,3,4-thiadiazoles

Autorzy

Turowska M. , G. Mlostoń G. , M. Celeda M. , J. Raczak J.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

Polarographic, linear-sweep cyclic voltammetric and coulometric at controlled potential studies of some 2,5-dihydro-1,3,4-thiadiazoles ( 3-1,3,4-thiadiazolines) on mercury electrodes have been performed in acetonitrile over pH range 1.2-13 in water-ethanol and water-acetonitrile mixtures with Britton-Robinson's buffer. Under conditions of present study, thiadiazoles are reduced to respective thiadiazolidines, and the N=N bond is reduced faster than the C=O group. All electrochemical reactions at pH < 7 are pH dependent and at pH > 7 influenced by surface characteristics. Electrode reaction mechanisms are presented and discussed.

Słowa kluczowe

2,5-dihydro-1,3,4-thiazoles (delta3-1,3,4-thiadiazolines electrochemical study structural effect

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2002

Tom

Vol. 76 / nr 6

Strony

839--855

Opis fizyczny

Bibliogr. 51 poz., rys.

Twórcy

autor

Turowska M.

Department of General and Inorganic Chemistry

autor

G. Mlostoń G.

Department of Organic and Applied Chemistry University of Łódź, ul. Narutowicza 68, 90-136 Łódź, Poland

autor

M. Celeda M.

Department of Organic and Applied Chemistry University of Łódź, ul. Narutowicza 68, 90-136 Łódź, Poland

autor

J. Raczak J.

Department of General and Inorganic Chemistry

Bibliografia

1. Mlostoń G., Romański J., Schmidt Ch., Reisenauer H.P. and Maier G., Chem. Ber., 127, 2527 (1994).
2. Petit M., Linden A., Mlostoń G. and Heimgartner H., Helv. Chim. Acta., 77, 1076 (1994).
3. Huisgen R., Penelle J., Mlostoń G., Buyle-Padias A. and Hall K. Jr., J. Am. Chem. Soc., 114,266 (1992).
4. Lund H., Disc. Faraday Soc., 45, 193 (1968).
5. Tsveniashvili V.S., Gaprindashvili W.N. and Havtasi N.S., Zh. Obshch. Khim., 42, 193 (1972).
6. Tsveniashvili V.S.,Gaprindashvili W.N.,CkalobadzeL.A. and Siergiejev W.A,,Zh. Obshch. Khim., 42, 2044 (1972); 43 2122(1973).
7. Sherman E.D., Lambert S. Jr. and Pilgram K., J. Heterocycl. Chem., 11, 763 (1974).
8. Tsveniashvili V.S., Eleklrokhimiya, 11, 523 (1975).
9. Wawzonek S. and Federickson J.D., J. Am. Chem. Soc., 77, 3988 (1955).
10. Milner G.W.C.. Polarografia., WNT, Warszawa 1962, p. 516, (in Polish).
11. Sadler J.S. and Bard A.J., J. Am. Chem. Soc., 90, 979(1968).
12. Florence T.M., Johnson D.A. and Batley G.E., J. Electroanal. Chem., 50, 13 (1974).
13. Laviron E., J. Electroanal. Chem., Ill, 337 (1980).
14. Roullier L. and Laviron E., J. Electroanal. Chem., 134, 18 (1982).
15. Tallec A., Electrochimie Organique, Masson, Paris 1985, pp. 11, 14, 25, 124, 128.
16. Fry A.J., Synthetic Organic Electrochemistry, 2nd ed. J.Wiley & Sons, NY 1989, p. 174, 198.
17. Rodrigez Mellado J.M. and Martin Galvin R., J. Electroanal. Chem., 267, 221 (1989).
18. Lund H., Coll. Czech. Chem. Commun., 31, 4175 (1966).
19. Lund H., Acta Chem. Scand., 21, 2525 (1967).
20. Lorance J. and Moinet C., Journees D ’Electrochimie 95, Strasbourg 1995, CA 8-12.
21. Mlostoń G. and Huisgen R., Tetrahedron Lett., 30, 7045 (1989).
22. Huisgen R., Mlostoń G. and Fulka C., Heterocycles, 23, 2207 (1985).
23. Turowska M., Mlostoń G. and Raczak J., Polish J. Chem., 67, 1 (1993).
24. Krapcho A.P., Rao D.R., Silvon M.P. and Abegaz B., J. Org. Chem., 36, 3885 (1971).
25. Huisgen R. and Mlostoń G., Heterocycles, 30, 737 (1990). Study of electrochemical behaviour of some 2,5-dihydro-1,3,4-thiadiazoles
26. Garratt P.J., Payne D. and Tocher D.A., J. Org. Chem., 55, 1909 (1990).
27. Bates R.G., Paabo M. and Robinson R.D., J. Phys. Chem., 67, 1833 (1963).
28. Bates R.G., “Determination of pH” (in Russian), Khimiya, Leningrad 1968.
29. Laviron J., J. Electroanal. Chem., 124, 19 (1981).
30. Heyrovsky M. and Vavricka S., J. Electroanal. Chem., 36, 203 (1972).
31. Galus Z., Fundamentals of Electrochemical Analysis, 2nd Edition, Ellis Horwood, NY, and Polish Scien¬tific Publ. PWN, Warsaw 1994, p. 286.
32. Nicholson R.S. and Shain I., Anal. Chem., 36, 706 (1964).
33. Rodriquez Mellando J.M. and Ruiz Montoya M.M., J. Electroanal. Chem., 365, 71 (1994).
34. Turowska M., Mlostoń G., Romański J. and Raczak J., a) Euroconference: 18th Sjendberg Meeting on Organic Chemistry, Sjendberg, Denmark 1994. Oral communication, b) Coll. Czech. Chem. Commun., 63,31 (1998).
35. Pasternak R., Helv. Chim. Acta., 31, 753 (1948).
36. Elving P.J. and Leone J.T., J. Am. Chem. Soc., 80, 1021 (1958).
37. Laviron E., Meunier-Prest R. and Mathieu E„ J. Electroanal. Chem., 371, 251 (1994).
38. Nejman M. and Markina S., ZavodskayaLab., 13, 1174 (1947).
39. Prelog V. and Hafliger O., Helv. Chim. Acta., 32, 2088 (1949).
40. Kabasakalian P. and Mc Glotten E., Anal. Chem., 31, 1091 (1959).
41. Wisner W. and Schwabe K., J. Electroanal. Chem., 15, 73 (1967).
42. Laviron E., J. Electroanal. Chem., 382, 111 (1995).
43. Brown E.R. and Sandifer J.R., Physical Methods of Chemistry., V. 11. Electrochemical Methods, A. Wiley, Interscience Publication, NY 1986, p. 301.
44. Mlostoń G. and Huisgen R., Tetrahedron Lett., 26, 1053 (1985).
45. Mlostoń G., Romański J., Linden A. and Heimgartner H., Helv. Chim. Acta, 80, 230 (1997).
46. Kolthoff I.M. and Bamun C., J. Am. Chem. Soc., 62, 3061 (1940).
47. Stricks W. and Kolthoff I.M., J. Am. Chem. Soc., 75, 5673 (1953).
48. Stankovich M.T. and Bard A.J., J. Electroanal. Chem., 75, 487 (1977).
49. Moore W.M. and Gaylor V.F., Anal. Chem., 49, 1387 (1977).
50. Costa Garcia A. and Tunon Blanco P., J. Electroanal. Chem., 245, 157 (1988).
51. Karpiński Z.J., Kamy M. and Kublik Z. ibid., 288, 129(1990).

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ1-0020-0095