Home Articles List Article Information
Iranian Journal of Chemistry and Chemical Engineering (IJCCE)
Journal Archive
Volume Volume 36 (2017)
Volume Volume 35 (2016)
Volume Volume 34 (2015)
Volume Volume 33 (2014)
Volume Volume 32 (2013)
Volume Volume 31 (2012)
Volume Volume 30 (2011)
Volume Volume 29 (2010)
Volume Volume 28 (2009)
Volume Volume 27 (2008)
Volume Volume 26 (2007)
Volume Volume 25 (2006)
Volume Volume 24 (2005)
Volume Volume 23 (2004)
Volume Volume 22 (2003)
Volume Volume 21 (2002)
Volume Volume 20 (2001)
Volume Volume 19 (2000)
Volume Volume 18 (1999)
Volume Volume 17 (1998)
Volume Volume 16 (1997)
Volume Volume 15 (1996)
Volume Volume 14 (1995)
Volume Volume 13 (1994)
Volume Volume 12 (1993)
Volume Volume 11 (1992)
Volume Volume 10 (1991)
Volume Volume 9 (1990)
Volume Volume 8 (1989)
Volume Volume 7 (1988)
Volume Volume 6 (1987)
Semnani, A., Firooz, A., Pouretedal, H., Nazari, B. (2004). Spectrophotometric Study of the Intreaction of some Benzo, Benzyl and Phnylcrown Ethers with Pi-Acceptor DDQ in Chloroform Solution. Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 23(1), 57-64.
Abolfazl Semnani; Ali Reza Firooz; Hamid Reza Pouretedal; Behzad Nazari. "Spectrophotometric Study of the Intreaction of some Benzo, Benzyl and Phnylcrown Ethers with Pi-Acceptor DDQ in Chloroform Solution". Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 23, 1, 2004, 57-64.
Semnani, A., Firooz, A., Pouretedal, H., Nazari, B. (2004). 'Spectrophotometric Study of the Intreaction of some Benzo, Benzyl and Phnylcrown Ethers with Pi-Acceptor DDQ in Chloroform Solution', Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 23(1), pp. 57-64.
Semnani, A., Firooz, A., Pouretedal, H., Nazari, B. Spectrophotometric Study of the Intreaction of some Benzo, Benzyl and Phnylcrown Ethers with Pi-Acceptor DDQ in Chloroform Solution. Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 2004; 23(1): 57-64.

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

Article 7, Volume 23, Issue 1, March and April 2004, Page 57-64  XML PDF (283 K)
Document Type: Research Article
Authors
Abolfazl Semnani 1; Ali Reza Firooz1; Hamid Reza Pouretedal2; Behzad Nazari2
1Department of Chemistry, Shahrekord University, P. O. Box 115, Shahrekord, I.R. IRAN
2Department 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.
Keywords
DDQ; Crown ethers; Spectrophotometry; Charge transfer complex
Main Subjects
Applied Chemistry; Organic Chemistry
References
[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).

Statistics
Article View: 1,591
PDF Download: 945