Spectrophotometric Study of the Intreaction of some Benzo, Benzyl and Phnylcrown Ethers with Pi-Acceptor DDQ in Chloroform Solution

Document Type: Research Article

Authors

1 Department of Chemistry, Shahrekord University, P. O. Box 115, Shahrekord, I.R. IRAN

2 Department of Chemistry, Malek-Ashtar University of Technology, Shahinshahr, I.R. IRAN

Abstract

The interaction between benzo-15-crown-5 (B15C5), dibenzo-18-crown-6 (DB18C6), dibenzyl-daza-18crown-6 (DBzDA18C6), N-phenyl-aza-15-crown-5 (NPhA15C5) and dibenzopyridine-18-crown-6 (DBPy18C6) with π-acceptor 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in chloroform solution was studied spectrophotometrically. The interaction of B15C5-DDQ and DB18C6-DDQ caused the formation of 1:1 charge transfer complexes through equilibrium reaction. The interaction of others caused the formation of 1:1 complexes in an equilibrium step and the conversion of the resulting adduct to D+DDQ- (D=NPhA15C5, DBPy18C6, DBzDA18C6) in a nonequilibrium step. The formation constant of DBzDA18C6 was evaluated by computer fitting of the absorbance mole ratio data. Other stability constants were evaluated through the Hildebrand method. It was found that the stabilities vary in the order: B15C5 < DB18C6 < DBPy18C6 < NPhA15C5 < DBzDA18C6. All of the resulting molecular complexes were isolated in crystalline form and characterized.

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[1] Cuningham, K. G., Dawson, W.  and Spring, F. S.,  J. Chem. Soc., 2305 (1951).
[2] Cretanovic, R. J., Duncan, F. J., Falconer, W. E. and Sunder, W. A., J. Am. Chem. Soc., 88, 1602 (1966).
[3] Newman, M.S., Lutzz W. B. and Lednicer, D., J. Am. Chem. Soc., 77, 3420 (1955).
[4] Kosower, E.M., J. Am. Chem. Soc., 80, 3253 (1958).
[5] Bryce M. R. and Murphy, I. C., Nature, 309 (1984).
[6] Izatt , R. M. , Pawlak , K. , Bradshaw , J. S. and Bruening, R. L., Chem. Rev., 91, 1721 (1991).
[7] Shamsipur, M., Semnani, A. and Mokhtarifard, A., Iranian Journal of Science & Technology, 18, 192 (1994).
[8] Semnani , A. and Shamsipur , M. , Polish J. Chem. , 70, 74 (1996).
[9] Domench, A., Navarro, P. and Revirego, F., Talanta, 51, 625 (2000)
[10] Semnani, A. and Shamsipur, M., J. Chem. Soc., Dalton Trans., 2215 (1996).
[11] Semnani,  A.  and  Shamsipur,  M.,  Polish J. Chem.,  95, 134 (1997).
[12] Bekin, M. A. and Yarkov, A. V., Spectrochim. Acta., 49(A), 531 (1999).
[13] Sharghi, H., Massah, A. R. and Abedi, M., Talanta, 49, 531 (1999).
[14] Proceeding of the 26th International Symposium on Macrocyclic Chemistry (ISMC 2001) Japan, 15-20 July (2001).
[15] Bensi, H. A. and Hildebrand, J. H., J. Am. Chem. Soc., 71, 2703 (1949).
[16] Nicely, V. A.  and Dye, J. L., J. Chem. Educ., 48, 443 (1971).
[17] Wenthworth, W. E.,  J. Chem. Educ., 42, 96 (1962).
[18] Powell, M. J. D., Comput. J., 7, 155 (1964).
[19] Beck, M.T. and Nagypal, I., “Chemistry of Complex Equilibria”, John Wiley & Sons (1990).
[20] Semnani, A.  and Shamsipur, M.,  Spectrochim. Acta., 49(A), 411 (1993).
[21] Nour - el-din, A. M.,  Spectrochim. Acta, 42(A), 637 (1976).
[22] Skoog, D.A., West, D. and Holler, J.F., “Funda-mentals of Analytical Chemistry”, Sounders College Publishing (1988).
[23] Huheey, J.E.,  “Inorganic Chemistry”, Harper & Pow Publishers (1983).
[24] Giorgio, T.  and Co-workers, Gazz, Chim. Ital., 119, 399 (1989).
[25] Arteburn, J. B., Tetrahedron, 57, 9765 (2001).
[26] Satoh, T. , Nakamura , A. and Iriuchijma , A. ,  Tetrahedron, 57, 9689 (2001).
[27] Bringmann, G. and Tasler, S., Tetrahedron, 57, 31 (2001).
[28] Ma, S.,  Zhang, X. D.  and  Shen, L. L., Journal of Photochemistry and Photobiology, 139, 97 (2001).
[29] Berry, R. F., Rice, S. A.  and Ross, J., “Physical Chemistry”, John Wiley & Sons (1980).