Solvatochromism and potentiometic studies of some active nitroso- and nitroso-azo- compounds

Mamdouh Saad Masoud; Ekram Abd El-Moniem Khalil; Saeda Abou El-Thana Abou El Enein; Hesham Mostafa Kamel

doi:10.5155/eurjchem.2.3.420-432.407

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Published: Sep 30, 2011

DOI: https://doi.org/10.5155/eurjchem.2.3.420-432.407

Keywords:

Nitroso, Pyridin-6-ylazo, Triazene, Effect of solvents, Potentiometry, Spectrophotometry

Section

Review Article

Issue

Vol. 2 No. 3 (2011): September 2011

Dates

Received 2011-02-16
Accepted 2011-04-16
Published 2011-09-30

Mamdouh Saad Masoud

Chemistry Department, Faculty of Science, Alexandria University, Alexandria, 21547, Egypt

Ekram Abd El-Moniem Khalil

Chemistry Department, Faculty of Science, Alexandria University, Alexandria, 21547, Egypt

Saeda Abou El-Thana Abou El Enein

Chemistry Department, Faculty of Science, Minufiya University, Shebin El-Kom, 32511, Egypt

Hesham Mostafa Kamel

Chemistry Department, Faculty of Science, Alexandria University, Alexandria, 21547, Egypt

Abstract

The stability studies of biologically active 2,4-dinitrosoresorcinol, o-carboxy phenylazo-dinitrosoresorcinol, N,N`-bis-[4,4`-(1,3-diphenyltriazine)]-diacetamide, 2-amino-6-phenylazo-pyridin-3-ol, 2-amino-3-hydroxy-pyridin-6-ylazo)-benzoic acid, 4-(2-amino-3-hydroxy-pyridin-6-ylazo)-benzoic acid ethyl ester and N-[4-(2-amino-3-hydroxy-pyridin-6-ylazo)-phenyl]-acetamide compounds were studied. The dissociation constants were determined potentiometrically. The thermodynamic parameters of dissociation were evaluated. Regression analysis is applied for correlating the different parameters. The results help to assign the solute-solvent interactions and the solvatochromic potential of the investigated compounds. The electronic character of the substituent and the chemical nature of the solvent are major factors for the observed solvatochromism.

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Masoud, M. S.; Khalil, E. A. E.-M.; El Enein, S. A. E.-T. A.; Kamel, H. M. Solvatochromism and Potentiometic Studies of Some Active Nitroso- and Nitroso-Azo- Compounds. Eur. J. Chem. 2011, 2, 420-432.

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References

[1]. Arranz, M. P.; Lopez, G. R.; Gutierrez, V. M. D.; Godino, S. M. L.; Mareno, J. M. Inorg. Chim. Acta 2000, 304, 137-143.
http://dx.doi.org/10.1016/S0020-1693(00)00070-0

[2]. Melguizo, M.; Marchal, A.; Nogueras, M.; Sanchez, A.; Low, J. N. J. Heterocyclic Chem. 2002, 39, 97-103.
http://dx.doi.org/10.1002/jhet.5570390114

[3]. Lopez, G. R.; Arranz, M. P.; Godino, S. M. L.; Gutierrez, V. M. D.; Perez, C. A.; Cobo, D. J.; Moreno, J. M. Inorg. Chim. Acta 2000, 308, 59-64.
http://dx.doi.org/10.1016/S0020-1693(00)00206-1

[4]. Yun, J.; Choi, H. Talanta 2000, 52(5), 893-902.
http://dx.doi.org/10.1016/S0039-9140(00)00441-0

[5]. Ghaly, A. E.; Dave, D.; Budge, S.; Brooks, M. S. Am. J. App. Sci. 2010, 7, 859-877.
http://dx.doi.org/10.3844/ajassp.2010.859.877

[6]. Foreti, B.; Burger, N.; Hankonyi, V. Polyhedron 1995, 14, 605-609.
http://dx.doi.org/10.1016/0277-5387(94)00280-R

[7]. Totsuka, Y.; Nishigaki, R.; Enomoto, S.; TakamuraEnya, T.; Masumura, K.; Nohmi, T.; Kawahara, N.; Sugimura, T.; Wakabayashi, K. Chem. Res. Toxicology 2005, 18(10), 1553-1562.
http://dx.doi.org/10.1021/tx050144x
PMid:16533019

[8]. Coss, A.; Cantor, K. P.; Reif, J. S.; Lynch, C. F.; Ward, M. H. Am. J. Epidem. 2004, 159, 7, 693-701.
http://dx.doi.org/10.1093/aje/kwh081
PMid:15033647

[9]. Kandil, S. S.; El-Hefnawy, G. B.; Bakr E. A.; Abou El-Ezz, A. Z. Trans. Met. Chem. 2003, 28, 168-175.
http://dx.doi.org/10.1023/A:1022968604281

[10]. Dinda, J.; Pal, S.; Ghosh, B. K.; Sinha, C.; Cheng, J.; Liao, F. L.; Lu, T. H. J. Coord. Chem. 2002, 55, 1271-1281.
http://dx.doi.org/10.1080/0095897021000041185

[11]. Rauth, G. K.; Dinda, J.; Jasimuddin, S.; Sinha, C. Trans. Met. Chem. 2003, 28, 88-95.
http://dx.doi.org/10.1023/A:1022557630011

[12]. Byabartta, P.; Pal, S.; Misra, T. K.; Sinha, C.; Liao, F. L.; Panneerselvam, K.; Lu, T. H. J. Coord Chem. 2002, 55, 479-495.
http://dx.doi.org/10.1080/00958970290020793

[13]. Pramanik, K.; Shivakumar, M.; Ghosh, P.; Chakravorty, A. Inorg. Chem. 2000, 39, 195-199.
http://dx.doi.org/10.1021/ic9908322
PMid:11272525

[14]. Shivakumar, M.; Pramanik, K.; Bhattacharyya, I.; Chakravorty, A. Inorg. Chem. 2000, 39, 4332- 4338.
http://dx.doi.org/10.1021/ic000356b
PMid:11196929

[15]. Shivakumar, M.; Gangopadhyay, J.; Chakravorty, A. Polyhedron 2000, 20, 2089-2093.
http://dx.doi.org/10.1016/S0277-5387(01)00812-9

[16]. Hotze, A. C. G.; Broekhuisen, M. E. T.; Velders, A. H.; Vander Schilden, K.; Haasnoot, J. G.; Reedijk, J. Eur. J. Inorg. Chem. 2002, 2, 369-376.
http://dx.doi.org/10.1002/1099-0682(20022)2002:2<369::AID-EJIC369>3.0.CO;2-H

[17]. Saha, A.; Majumdar, P.; Peng, S. M.; Goswami, S. Eur. J. Inorg. Chem. 2000, 12, 2631â2639.

[18]. Masoud, M. S.; Abou El-Enein, S. A.; Obeid, N. A. Z. Fur Phys. Chem. 2001, 215, 7, 867-881.

[19]. Masoud, M. S.; Abou El-Enein, S. A.; Kamel, H. M. Ind. J. Chem. 2002, 41A, 297-303.

[20]. Masoud, M. S.; Mohamed, G. B.; Abdul Razek, Y. H.; Ali, A. E.; Khiry, F. N. Spectroscopy Lett. 2002, 35, 377-413.
http://dx.doi.org/10.1081/SL-120005674

[21]. Masoud, M. S.; Abou El-Enein, S. A.; Ayad, M.; Goher, A. S. Spectrochim. Acta A 2004, 60(1), 77- 87.
http://dx.doi.org/10.1016/S1386-1425(03)00226-9

[22]. Masoud, M. S.; Khalil, E. A.; Hafez, A. M.; El-Husseiny, A. F. Spectrochim. Acta A 2005, 61, 989 - 993.
http://dx.doi.org/10.1016/j.saa.2004.05.042
PMid:15683807

[23]. Masoud, M. S.; El-Husseiny, A. F.; Abd El-Ghany, M. M.; Hammud, H. H. Bull. Fac. Sci. Alex. Univ. 2006, 44(1,2), 41- 54.

[24]. Masoud, M. S.; Khalil, E. A.; Ramadan, A. M. J. Anal. & App. Pyrolysis 2007, 78(1), 14-23.
http://dx.doi.org/10.1016/j.jaap.2006.03.005

[25]. Masoud, M. S.; Khalil, E. A.; Ramadan, A. M.; Gohar, Y. M.; Sweyllam, A. Spectrochim. Acta 2007, 67A, 669- 677.
http://dx.doi.org/10.1016/j.saa.2006.07.047
PMid:17030149

[26]. Masoud, M. S.; Abou El-Enein, S. A.; Ramadan, A. M.; Goher, A. S. J. Anal. & App. Pyrolysis 2008, 81, 45-51.
http://dx.doi.org/10.1016/j.jaap.2007.08.002

[27]. Van V. L. G.; Hass, C. G. J. Am. Chem. Soc. 1953, 75, 451-455.
http://dx.doi.org/10.1021/ja01098a057

[28]. Reichardt, C. Chem. Rev. 1994, 94, 2319-2358.
http://dx.doi.org/10.1021/cr00032a005

[29]. Hilliard, L. J; Foulk, D. S.; Gold, H. S. Anal. Chim. Acta 1981, 133, 319-327.
http://dx.doi.org/10.1016/S0003-2670(01)83204-9

[30]. Masoud, M. S.; Hasanein, A. A.; Heiba, A. M. Spectrosc. Lett. 1984, 17, 441-453.
http://dx.doi.org/10.1080/00387018408062702

[31]. Masoud, M. S.; Khalil, E. A. Polish J. Chem. 1991, 65, 933-943.

[32]. Masoud, M. S.; Hasanein, A. A.; Ghonaim, A. K.; Khalil, E. A.; Mahmoud, A. A. Z. Fur. Phys. Chem. Bd. 1999, 209S, 223-238.

[33]. Masoud, M. S.; Ali, A. E.; Shaker, M. A.; Abdul Ghani, M. Spectrochim. Acta 2004, 60A, 3155-3159.
http://dx.doi.org/10.1016/j.saa.2004.02.030
PMid:15477158

[34]. Kirkwood, J. G. J. Chem. Phys. 1934, 2, 351-361.

[35]. David, J. G.; Hallam, H. E. Spectrochim. Acta 1967, 23 A, 593-603.

[36]. McRae, E. G. J. Phys. Chem. 1957, 61, 562-572.
http://dx.doi.org/10.1021/j150551a012

[37]. Fowler, F. W.; Katritzky, A. R.; Rutherford, R. J. D. J. Chem. Soc. (B) 1971, 460-469.
http://dx.doi.org/10.1039/j29710000460

[38]. Hantzsch, A. Ber. Dtsch. Chem. Ges. 1922, 55, 953-979.
http://dx.doi.org/10.1002/cber.19220550420

[39]. Franck, J. J. Trans. Faraday Soc. 1926, 21, 536-542.
http://dx.doi.org/10.1039/tf9262100536

[40]. Dearden, J. C.; Forbes, W. F. Can. J. Chem. 1960, 38(6), 896-910.
http://dx.doi.org/10.1139/v60-127

[41]. Masoud, M. S.; Ali, G. Y. J. Chin. Chem. Soc. (Taipei) 1981, 28, 103-106.

[42]. Masoud, M. S.; Hammad, H. H. Spectrochim. Acta 2001, 57 A, 977-984.

[43]. Masoud, M. S.; Ali, A. E.; Shaker, M. A.; Abdul Ghani, M. Spectrochim. Acta 2005, 61A, 3102-3107.
http://dx.doi.org/10.1016/j.saa.2004.10.043
PMid:16165059

[44]. Kim, J. J.; Funabiki, K.; Muramatsu, H.; Shibata, K.; Kim, S. H.; Shiozaki, H.; Hartmann, H.; Matsui, M. J. Chem. Soc. Perkin Trans. 2001, 2. 379-387.
http://dx.doi.org/10.1039/b006991o

[45]. Monahan, A. R.; De Luca, A. F.; Ward, A. T. J. Org. Chem. 1971, 36, 3838-3842.
http://dx.doi.org/10.1021/jo00823a619

[46]. Ramaekers, R.; Dehaen, W.; Adamowicz, L.; Maes, G. J. Phys. Chem. A 2003, 107, 1710-1719.
http://dx.doi.org/10.1021/jp012744k

[47]. Patrick, R. A.; Svehla, G. Anal. Chim. Acta 1977, 88, 363-370.
http://dx.doi.org/10.1016/S0003-2670(01)95911-2

[48]. Masoud, M. S.; Kaddah, A. M.; Khalil, A. M.; Tawfik, N. I. Indian J. Chem. 1979, 17A, 502-504.

[49]. Jahagirdar, D. V.; Khanolkar, D. D. J. Inorg. Nucl. Chem. 1973, 35, 921-930.
http://dx.doi.org/10.1016/0022-1902(73)80462-2

[50]. Charberk, S.; Martell, A. E. J. Am. Chem. Soc. 1952, 74, 5052-5056.
http://dx.doi.org/10.1021/ja01140a018

[51]. Khalil, E. A.; Masoud, M. S.; El-Marghany, A. M. Pak. J. Sci. Ind. Res. 1993, 36, 68-73.

[52]. Mui, K.; McBryde. W.; Neiboer, E. Can. J. Chem. 1974, 52, 1821-1833.
http://dx.doi.org/10.1139/v74-261

[53]. Kreshkov, A. P. Talanta 1970, 17, 1029-1044.
http://dx.doi.org/10.1016/0039-9140(70)80095-9

[54]. Coetzee, J. F.; Ritchie, C. D. Solute-Solvent Interactions. Marcel Dekker. New York, 1969, pp. 221.

[55]. Denison, J. T.; Ramsey, J. B. J. Am. Chem. Soc. 1955, 77, 2615-2621.
http://dx.doi.org/10.1021/ja01614a085

[56]. Yeh, S. J.; Jaffe, H. H. J. Am. Chem. Soc. 1959, 81, 3279-3283.
http://dx.doi.org/10.1021/ja01522a031

[57]. Martell, A. E.; Mutekaities, R. J. Determination and Use of Stability Constants, VCH, New York, 1992.

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