Interaction of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone with aza-18-crown-6 and aza-12-crown-4. Kinetic and spectrophotometric studies in chloroform and acetonitrile solutions

Abstract

Interactions of aza-18-crown-6 and aza-12-crown-4 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) have been examined spectrophotometrically in chloroform and acetonitrile solutions. The results indicate immediate formation of an electron donor–acceptor complex, DA [reaction (a)], which is followed by two relatively slow consecutive reactions (b). Pseudo-first-order rate constants at various temperatures for the formation of the ionic intermediate [D⁺A^–] and the final product have been evaluated by computer fitting of the absorbance–time data to appropriate equations. The formation constants of the resulting EDA complexes have also been determined. The influences of both the azacrowns’ structure and the solvent properties on the formation of EDA complexes and the rates of subsequent reactions are discussed.

References

1. C. J. Pedersen, J. Am. Chem. Soc., 1967, 89, 7017.
2. J. J. Christensen, J. O. Hill and R. M. Izatt, Science, 1971, 174, 459.
3. M. Newcomb and D. J. Cram, J. Am. Chem. Soc., 1975, 97, 1257.
4. R. M. Izatt, K. Pawlak, J. S. Bradshaw and R. L. Bruening, Chem. Rev., 1991, 91, 1721.
5. R. Malini and V. Krishnan, J. Phys. Chem., 1980, 84, 551.
6. Y. Jayathirtha and V. Krishnan, Indian J. Chem., Sect. A, 1981, 20, 249.
7. A. M. Noor El-Din, Spectrochim. Acta, Part A, 1986, 42, 637.
8. L. J. Andrews and R. M. Keefer, J. Org. Chem., 1988, 53, 537.
9. E. M. Nour, Spectrochim. Acta, Part A, 1991, 44, 1277.
10. A. H. Rady, Spectrosc. Lett., 1992, 25, 537.
11. R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 1992, 92, 1261.
12. A. Semnani and M. Shamsipur, Spectrochim. Acta, Part A, 1993, 49, 411.
13. A. Semnani and M. Shamsipur, J. Inclusion Phenom., 1995, 22, 99.
14. A. Semnani and M. Shamsipur, J. Chem. Soc., Dalton Trans., 1996, 2215.
15. A. Semnani and M. Shamsipur, Pol. J. Chem., 1997, 71, 134.
16. M. Hasani and M. Shamsipur, J. Incl. Phenom., 1997, 28, 39.
17. T. Nogami, K. Yoshihara, H. Hosoya and S. Nagakura, J. Phys. Chem., 1969, 73, 2670.
18. W. J. Lautenberger and J. G. Miller, J. Phys. Chem., 1970, 74, 2722.
19. P. C. Dwivedi, A. K. Banga and R. Agarwal, Electrochim. Acta, 1982, 27, 1697.
20. P. C. Dwivedi, A. K. Banga and A. Gupta, Electrochim. Acta, 1983, 28, 8083.
21. P. C. Dwivedi and R. Agarwal, Indian J. Chem., Sect. A, 1984, 23, 366.
22. G. Tosi, P. Bruni and L. Cardellini, Gazz. Chim. Ital., 1984, 114, 125.
23. A. F. E. Morad, Rev. Roum. Chim., 1988, 33, 617.
24. M. M. Shoukry and R. Koussini, Bull. Soc. Chim. Fr., 1991, 465.
25. F. Gutmann, J. Sci. Ind. Res., 1967, 26, 19.
26. G. M. Eckert, F. Gutmann and H. Keyzer, in Electropharmacology, eds. G. M. Eckert, F. Gutmann and H. Keyzer, CRC Press, Boca Raton, FL, 1990, pp. 1–23.
27. R. V. Ball, G. M. Eckert, F. Gutmann and D. K. Y. Wong, Anal. Chem., 1994, 66, 1198.
28. W. J. Middleton, E. L. Little, D. D. Coffman and V. A. Engelhardt, J. Am. Chem. Soc., 1958, 80, 2795.
29. S. Matsuzaki, T. Mitsuishi and K. Toyoda, Chem. Phys. Lett., 1982, 91, 296.
30. J. S. Miller, J. P. Krusic, D. A. Dixon, M. W. Reiff, H. J. Zhang, C. E. Anderson and J. A. Epstein, J. Am. Chem. Soc., 1986, 108, 4459.
31. E. M. Abd-Alla, Can. J. Appl. Spectrosc., 1993, 38, 88.
32. B. K. Das and B. Majee, J. Indian Chem. Soc., 1968, 45, 1054.
33. P. C. Dwivedi and A. K. Banga, J. Phys. Chem., 1981, 85, 1768.
34. T. Nagami, T. Yamaoka, K. Yoshihara and S. Nagakura, Bull. Chem. Soc. Jpn., 1971, 44, 380.
35. K. Kouno, C. Ogawa, Y. Shimomura, H. Yano and Y. Ueda, Chem. Pharm. Bull., 1981, 29, 301.
36. A. A. Frost and R. G. Pearson, Kinetics and Mechanism, Wiley, New York, 2nd edn., 1961, p. 166.
37. V. A. Nicely and J. L. Dye, J. Chem. Educ., 1971, 48, 443.
38. W. E. Wentworth, J. Chem. Educ., 1962, 42, 96; 162.
39. M. J. D. Powell, Comput. J., 1964, 7, 155.
40. V. Gutmann, The Donor-Acceptor Concepts of Molecular Interactions, Plenum, New York, 1978.
41. T. Yamabe, K. Hori, K. Akagi and K. Fukui, Tetrahedron, 1972, 35, 1065.
42. M. J. Bovill, D. J. Chadwick and I. O. Sutherl, J. Chem. Soc., Perkin Trans. 2, 1980, 1529.
43. J. D. Dunitz and P. Seiler, Acta Crystallogr., Sect. B, 1974, 30, 2739.
44. F. A. L. Anet, J. Krane, J. Dale, K. Daasvatn and P. O. Kristians, Acta Chem. Scand., 1973, 27, 3395.
45. S. Itoh, J. Maruta and S. Fukuzumi, J. Chem. Soc., Perkin Trans. 2, 1996, 1429.
46. H. M. A. Salman, S. A. El-Gyar, M. M. A. Hamed and M. A. El-Gahami, Can. J. Appl. Spectrosc., 1992, 37, 137.