European Journal of Chemistry

Spectrophotometric studies on some arylazo diamino pyrimidinol in organic solvents and in buffer solutions



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Nadia Ahmed Abdalla
Mohamed Tawfek El-Haty
Farok Abd-Elkarim Adam
Fatma Wafdy Hassan

Abstract

The spectral behavior of some new arylazo-2,6-diamino-4-pyrimidinol in pure and mixed organic solvents and buffer solutions of varying pH have been studied. The observed bands are assigned to the possible electronic transition. The band appearing in the visible region is assigned to p→p* transition involving p-electronic system of the whole compounds, associated with intramolecular charge transfer. This charge transfer seems to originate from the aryl moiety to the pyrimidine ring which is characterized by accepting character. This behavior can be explained that these compounds exist in the hydroxyazo-quinoid hydrazon tautomreic explained equilibrium. The possibility of the formation of a-H-bond solvated molecular complex between the molecule of azo 2,6-diaminopyrimidinol and proton-acceptor solvents of DMSO and DMF molecular were discussed. The pK values of these compounds were determined and on the basis of the relative contribution of acidic basic character of respective species.


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Abdalla, N. A.; El-Haty, M. T.; Adam, F. A.-E.; Hassan, F. W. Spectrophotometric Studies on Some Arylazo Diamino Pyrimidinol in Organic Solvents and in Buffer Solutions. Eur. J. Chem. 2014, 5, 41-52.

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References

[1]. Klyansundaram, K.; Gratzel, M. J. Coord. Chem. 1998, 177, 347-414.
http://dx.doi.org/10.1016/S0010-8545(98)00189-1

[2]. Uma, R.; Palaniandavar, M.; Butcher, R. J. J. Chem. Soc., Dalton Trans. 1996, 2061-2066.
http://dx.doi.org/10.1039/dt9960002061

[3]. Nagao, H.; Ooyama, D.; Hirano, T.; Naoi, H.; Shimada, M.; Sasaki, S.; Nagao, N.; Mukaida, M.; Takao, O. Inorg. Chim. Acta 2001, 320, 60-66.
http://dx.doi.org/10.1016/S0020-1693(01)00468-6

[4]. Argazzi, R.; Bignozzi, C. A.; Hasselmann, G. M.; Meyer, G. J. Inorg. Chem. 1998, 37, 4533-4537.
http://dx.doi.org/10.1021/ic980340+

[5]. Constable, E. C. Coord. Chem. Rev. 1989, 93, 205-223.
http://dx.doi.org/10.1016/0010-8545(89)80016-5

[6]. Zrenner, R.; Stitt, M; Sonnewald, M.; Boldt, R. Annu Rev Plant .2006, 57, 805-863.
http://dx.doi.org/10.1146/annurev.arplant.57.032905.105421

[7]. Colacio, E.; Dominguez-Vera, J. M.;Costes, J.P.; Kivekas, R.; Laurent, J. P. Ruiz, J.; Sundberg, M. J. Inorg. Chem. 1992, 31, 774-778
http://dx.doi.org/10.1021/ic00031a016

[8]. Cookson, P. D.; Tiekimk, R. T. J. Chem. Soc., Dalton Trans. 1993, 259-263.
http://dx.doi.org/10.1039/dt9930000259

[9]. Hung, C. Y.; Wang, T. L.; Jang, Y.; Kim, W. Y.; Schmehl, R. H.; Thummel, R. P. Inorg. Chem. 1996, 35, 5953-5956.
http://dx.doi.org/10.1021/ic960409i

[10]. Real, J. A.; Munoz, M. C.; Andres, E.; Granier, T.; Gallios, B. Inorg. Chem. 1994, 33, 3587-3594.
http://dx.doi.org/10.1021/ic00094a023

[11]. Yamamoto, T.; Zhou, Z.; Kanbara, T.; Shimura, M.; Kizu, K.; Maruyama, T.; Nakamura, Y.; Fukuda, T.; Lee, B.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K.; Sasaki, S. J. Am. Chem. Soc. 1996, 118, 10389-10399.
http://dx.doi.org/10.1021/ja961550t

[12]. Hansongnern, K.; Tempiam, S.; Liou, J. C.; Liao, F. L.; Lu, T. H. Anal. Sci. 2003, 19, 13-14.
http://dx.doi.org/10.2116/analsci.19.971

[13]. Masoud, M. S.; Mostafa, A. Z.; Ahmed, R. H.; Abd El Moneim, N. H. Molecules 2003, 8, 430-438.
http://dx.doi.org/10.3390/80500430

[14]. Buzykin, B. I.; Sorokin, M. Y.; Krivolapov, D. B.; Gubaidullin, A. T.; Litvinov, I. A. Chem. Heterocyc. Compd. 2002, 38, 1348-1356.
http://dx.doi.org/10.1023/A:1022178425960

[15]. Tsupak, E. B.; Shevchenko, M. A.; Tkachenko, Y. N.; Nazarov, D. A. Russ. J. Org. Chem. 2002, 38(6), 880-888.
http://dx.doi.org/10.1023/A:1020311809423

[16]. Kaupp, G.; Herrmann, A.; Schmeyers, J. Chem. Eur. J. 2002, 8(6), 1395-1406.
http://dx.doi.org/10.1002/1521-3765(20020315)8:6<1395::AID-CHEM1395>3.0.CO;2-L

[17]. Moreno, J. M.; Ruiz, J.; Dominguez-Vera, J. M.; Calacio, E. Inorg. Chim. Acta 1993, 208(1), 111-115.
http://dx.doi.org/10.1016/S0020-1693(00)82893-5

[18]. Masoud, M. S.; Ghonaim, A. K.; Ahmed, R. H.; Mahmoud, A. A.; Ali, A. E. Z. Phys. Chem. 2001, 215(4), 531-542.

[19]. Masoud, M. S.; El-Enein, S. A.; Obeid, N. A. Z. Phys. Chem. 2001, 215(7), 867-881.

[20]. Abdel-Razik, H. H.; Refat, Hala, M.; Zaki, M. E. A. Heterocycl. Commun. 2001, 7(3), 263-270.

[21]. Kletskii, M. E.; Tsupak, E. V. Chem. Heterocyc. Compd. 2001, 37(10), 1238-1240.
http://dx.doi.org/10.1023/A:1013849527302

[22]. Madkour, H. M. F.; Mahmoud, M. R.; Nassar, M. H.; Habashy, M. M. Molecules 2000, 5, 746-755.
http://dx.doi.org/10.3390/50500746

[23]. Gupta, S. P.; Sharma, S.; Goel, R. K. Spectrochim. Acta A 1986, 42, 10, 1163-1171.
http://dx.doi.org/10.1016/0584-8539(86)80071-X

[24]. Goel, R. K. Spectrochimica Acta A 1984, 40, 723-732.
http://dx.doi.org/10.1016/0584-8539(84)80096-3

[25]. Roubsnd, D. B.; Kister, J.; Bonscasse, L.; Metzer, J. Spectrosc. Lett. 1981, 14,431-439.
http://dx.doi.org/10.1080/00387018108062603

[26]. Scudero, F. E.; Mo, O.; Yamez, M. J. Chem. Soc., Perkin Trans. 1983, 11, 1735-1739.

[27]. Martin, R. B.; Mariam, Y. H. Met. Ions Biol. Syst. 1979, 8, 57-124.

[28]. Hug, W.; Tinocoo, J. J. J. Am. Chem. Soc. 1973, 95, 2803-2813.
http://dx.doi.org/10.1021/ja00790a010

[29]. Amrallah, A. H.; Abdalla, N. A.; El-Haty, E. Y. J. Chin. Chem. Soc. Taip 2006, 53(3), 697-706.

[30]. Britton, H. T. S. In Hydrogen ions, 4th Edi., Chapmann and Hill, London, 1954, pp. 217.

[31]. Douheret, G. Bull. Soc. Chim. Fr. 1967, 11, 1409-1413.

[32]. Hammam, A. M.; Issa, R. M.; Amin, S. A.; Dissouki, H. Gazz. Chim. Ital. 1979, 109, 351-355.

[33]. Issa, Y. M.; Abdel-Gani, N. T.; Aboudan, M. O. J. Indian Chem. Soc. 1983, 60, 24-26.

[34]. Berrie, A. H.; Hampson, P.; Longworth, S. W.; Mathias, A. J. Chem. Soc. B 1968, 1308-1310.
http://dx.doi.org/10.1039/j29680001308

[35]. Dessouki, H. A.; Killa, H. M.; Zaghloul, A. Spectrochim. Acta A 1986, 42, 631-635.
http://dx.doi.org/10.1016/0584-8539(86)80146-5

[36]. Sen, D.; Bhowmik, S.; Sengupta, P. J. Indian Chem. Soc. 1986, 63, 420-424.

[37]. Nakamura, M.; Sakanashi, Y.; Chikushi, H.; Kai, F.; Sato, S.; Uchikawa, S. Talanta 1987, 34, 369-371.
http://dx.doi.org/10.1016/0039-9140(87)80050-4

[38]. Staab, H. A.; Brettschneider, H.; Breunner, H. Chem. Ber. 1970, 103, 11011-11016.

[39]. Ahmed, Z. A.; Atta, F. M.; Abdalla, M. A.; Abdelmonem, M. E.; Metwally, S. Spectrochim. Acta A 1989, 45, 699-703.
http://dx.doi.org/10.1016/0584-8539(89)80254-5

[40]. Kantlehner, J.; Mezger, E. V.; Stoyanov, S. M.; Zakeeruddin, M. Chem. Rev. 1980, 33, 251-266.

[41]. Masoud, M. S.; Zaki. Z. M.; Ismail. F. M.; Mohamed, A. K. J. Phys. Chem. 1994, 185(2), 223-227.

[42]. Beaton, H. G.; Willey, G. R.; Drew, M. G. B. J. Chem. Soc., Perkin Trans. 1987, 2, 469-470.
http://dx.doi.org/10.1039/p29870000469

[43]. Hodgson, D. M.; Gibbs, A. R.; Drew; M. G. B. J. Chem. Soc., Perkin Trans. I 1999, 24, 3579-3590.

[44]. Ruiz, J.; Calacio, E.; Lopez-Gonzalez, J. D.; Sundberg, M.; Kivekas, R. J. Chem. Soc., Dalton Trans. 1990, 9, 2747-2752.
http://dx.doi.org/10.1039/dt9900002747

[45]. Issa, I. M.; Mahmoud, R. M.; Temerik, Y. M. Z. J. Phys. Chem. 1973, 253, 289-306.

[46]. Navas, D. J. Photochem. Photobiol. Chem. 990, 53, 41-50.

[47]. Candida, M.; Vaz, T. A.; Frauto Dasilva, J. J. J. Inorg. Nucl. Chem. 1981, 43, 1573-1578.
http://dx.doi.org/10.1016/0022-1902(81)80340-5

[48]. Amin, A. S.; Mohammed, T. Y. Talanta 2001, 54(4), 611-620.
http://dx.doi.org/10.1016/S0039-9140(00)00679-2

[49]. Singh, I.; Saini, R. Talanta 1994, 41(12), 2173-2175.
http://dx.doi.org/10.1016/0039-9140(94)00176-6

[50]. Swaminathan, M.; Dogra, S. K. J. Am. Chem. Soc. 1983, 105, 6220-6223.
http://dx.doi.org/10.1021/ja00358a005

[51]. Shulman; S. G. J. Pharm. Sci. 1971, 60, 371-374.

[52]. Mahmoud, M. R.; Ibrahim, S. A.; Hamed, M. M. Spectrochim. Acta A 1983, 39, 924-927.
http://dx.doi.org/10.1016/0584-8539(83)80119-6

[53]. Pilpenko, A. T.; Savransky, L. I. Talanta 1987, 34, 77-86.
http://dx.doi.org/10.1016/0039-9140(87)80011-5

[54]. Borges, C. P. F.; Tabak, M. Spectrochim. Acta A 1994, 50(6), 1047-1054.
http://dx.doi.org/10.1016/0584-8539(94)80026-X

[55]. Gutierrez, M. D.; Lopez, R.; Romero, M. A.; Salas, M. Can. J. Chem. 1988, 66, 249-255.
http://dx.doi.org/10.1139/v88-042

[56]. Amrallah, A. H.; Abdalla, N. A.; El-Haty, E. Y. Monatsh. Chem. 1997, 128, 1073-1084.
http://dx.doi.org/10.1007/BF00807557

[57]. Pati, S. The chemistry of hydrazo, azo and azoxy groups, Part 2, John-Willey and Sons, London, 1975, pp. 845-854.

[58]. Haselbach, E. Helv. Chim. Acta 1970, 53, 1526-1526.
http://dx.doi.org/10.1002/hlca.19700530638

[59]. Lurie, J., Hand book of analytical chemistry, Mir publishers, Moscow, Translated the Russian by Bobrov, N. 1974, pp. 275.

[60]. Foster, R.; Thomson, T. T. Faraday Soc. 1962, 58, 860-868.
http://dx.doi.org/10.1039/tf9625800860

[61]. Bhaskar, K. R.; Gosavi, R. K.; Rao, C. N. R. T. Faraday Soc. 1966, 31, 333-343.

[62]. Mishra, A. K.; Dogra, S. K. J. Photochem. 1985, 6, 81-88.

[63]. Zeynel, S. Arkivoc 2009, 7, 42-57.

[64]. Seferoglu, Z.; Ertan, N. Cent. Eur. J. Chem. 2008, 6, 81-88.
http://dx.doi.org/10.2478/s11532-007-0062-4

[65]. Shulman, S. G.; Kovi, P.J.; Young, J. F. J. Pharm. Sci. 1973, 62, 1197-1199.
http://dx.doi.org/10.1002/jps.2600620732

[66]. Gutierrez, M. D.; Lopez, R.; Romero, M. A.; Salas, M. Can. J. Chem. 1988, 66, 249-255.
http://dx.doi.org/10.1139/v88-042

[67]. Abed, N. M.; Nashed, B.; Fahmy, H. M.; Abdel, A. M. Monatsh. Chem. 1986, 117, 799-803.
http://dx.doi.org/10.1007/BF00817896

[68]. Miyadera T.; Kosower, E. M. J. Med. Chem. 1972, 15(5), 534-537.
http://dx.doi.org/10.1021/jm00275a024

[69]. Haselbach, E.; Girault, H.; Bernard, T. Helv. Chim. Acta 1999, 82, 1211-1222.
http://dx.doi.org/10.1002/(SICI)1522-2675(19990804)82:8<1211::AID-HLCA1211>3.0.CO;2-K

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Department of Chemistry, Aswan Faculty of Science, Aswan University, Aswan, Egypt
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