Monoazo Resorsinol Türevlerinin Spektroskopik Yöntemle Tautomerik Dengelerinin Hesaplanması (Calculation of Tautomeric Equilibrium of Monoazo Resorsinol Derivatives by Spectroscopic Method)

Öz

Anahtar Kelimeler

• -

Monoazo Resorsinol Türevlerinin Spektroskopik Yöntemle Tautomerik Dengelerinin Hesaplanması

Öz

Bu çalışmada bazı sübstitüe aminobenzen ve benzen-1,3-diol bileşiklerinin reaksiyonundan monoazo boyar maddeleri sentezlendi. Sentezlenen tüm bileşiklerin yapıları spektroskopik yöntemler ile aydınlatıldı. Elde edilen ortohidroksimonoazo bileşiklerinin tautomerik özellikleri UV-Vis. spektrofotometrik metodu ile polar ve apolar (DMSO, dimetil sülfoksit; EtOH, etanol; CHCl3, kloroform; C6H, benzen ve C6H12, siklohekzan) saf çözücü ortamları ile bu çözücülerin asidik ve bazik çözeltilerinde 25±1oC, 35±1oC ve 45±1oC sıcaklıklarda incelendi. Tüm bileşiklerdeki yüzde keto-amin tautomerisi hesaplandı.

Anahtar Kelimeler

• tautomerizm, benzen-1,3-diol, monoazo, spektroskopik yöntem

Kaynakça

1. Berber, H.; Öğretir, C.; Lekesiz E. Ç. S., and Ermiş E., ‘Spectroscopic Determination of Acidity Constants of Some Monoazo Resorcinol Derivatives’, J. Chem. Eng. Data 2008, 53, 1049–1055.
2. Corwin, H., Leo, A., and Taft, R. W. ‘A survey of Hammett Substituent Constants and Resonance and Field Parameters’, Chem. Rev., (1991), 91 (2), pp.168.
3. Dalton, L.R.; Harper, A.W.; Ghosn, R.; Steier, W.H.; Ziari, M.; Fetterman, H.; Shi, Y.; Mustacich, R.V.; Jen, A.K.Y. and Shea, K., ‘Synthesis and Processing of Improved Organic Second-Order Nonliear Optical Materials for Applications in Photonics’, J. Chem. Mater., 7 (1995), pp.1060-1081.
4. Dalton, L.R.; Harper, A.W.; Wu B.; Ghosn, R.; Laquindanum, J.; Liang, Z.; Hubbel, A. and Xu, C., Adv. Mater., 7 (1995), pp.519-540.
5. Dippy, J.F.J.; Hughes, S.R.C.; Rozanski, A., ‘The dissociation constants of some symmetrically disubstituted succinic acids’ J. Chem. Soc. (1959), 2492-2498.
6. Hashim, A.B.; Elie, A.J. and Noel, C., ‘Unusal and Efficient (Z)-Steroselective Peterson Synthesis of 2- Diethoxyphosphonyl-1-Alkoxy 3-Methylpenta-1,3-Diens. Their Use in The Diels-Alder Reaction’, Tetrahedron Lett., 37 (1996), pp.2951-2954.
7. Hayvalı, Z.; Hayvalı, M, Kılıç, Z.; Hökelek, T. and Weber, E., ‘New Benzo-15-Crown-5 Ethers Featuring Salicylic Schiff Base Substitutions –Synthesis, Complexes And Structural Study’ Journal of Inclusion Phenomena and Macrocyclic Chemistry, 45 (2003), pp.285–294.
8. Jaffé H. H. and Gardner, R. W., ‘Tautomeric Equilibria. IV. The Basicities of Monosubstituted Azobenzenes. An Acidity Scale in 20% Ethanolic Aqueous Sulfuric Acid’ J. Am. Chem. Soc.; 80(2) (1958), pp.319- 323.

9. Johnson, C. D. The Hammett Equation; (Cambridge University Press: New York, 1973).
10. Klotz, I. M., Fiess, H. A., Chen Ho, J. Y., and Mellody, M. ‘The Position of the Proton in Substituted Azobenzene Molecules’, J.Am. Chem. Soc., 76 (1954) 5136-5140.
11. Kumar, G.S., Azo Functional Polymers: Functional Group Approach in Macromolecular Design (Basel, Technomic Publishing co. Inc: Lancaster, 1999).
12. Little, R.D. and Venegas, G., ‘A new, mild method for the synthesis of azo compounds’, J. Org. Chem, 43 (1978), pp.2921-2923.
13. Peters, A.T. and Freeman, H.S., Colour Chemistry: The Design and Synthesis of Organic Dyes and Pigments (Elsevier Applied Science, London and New York 1991, pp.90-103).
14. Perrin, D. D., Dissociation Constants of Organic Bases in Aqueous Solution, (Butterworths, London, 1965; Supplement, 1972).
15. Prasad, P. and Williams, D., Introduction to nonlinear optical effects in molecules and polymers (New York USA: John Wiley and Sons, 1991).
16. Reeves, R. L. ve Kaiser, R. S., ‘Selective Solvation of Hydrophobic Ions in Structured Solvents. Azo- Hydrazone Tautomerism of Azo Dyes in Aqueous Organic Solvents’, J. Org. Chem.; 35(11) (1970), pp.3670-3675.
17. Rogers, M. T., Campbell, T. W. and Maatman, R. W., ‘The Ionization Constants of Some p-Substituted p’- Dimethylaminoazobenzenes1’, J. Am. Chem. Soc.; 73(11) (1951), pp.5122-5124.
18. Sawicki, E. ‘Physical Properties of the Aminoazobenzene Dyes. IV. The Position of Proton Addition’, J. Org. Chem. 22 (4), (1957), pp 365–367.
19. Shawali, A.S.; Harb, N.M.S. and Badahdah, K.O., J. Heterocycl. Chem. 22 (1985), pp.1397.
20. Vogel, A. I., Vogel’s textbook of quantitative chemical analysis (Revised by J. Mendham [et al.].–6th ed.– Harlow, England: Prentice Hall, 2000, pp.920-945).
21. Wang, W.; Gong, S.; Chen, Y.; Meng, I. ‘The Effects of Intramolecular Hydrogen Bonding on the Reaction of Phenols with Epoxide in the Presence of Nano Calcium Carbonate’, Supramol. Chem. 18 (4), (2006), 311–315.
22. Xie, S.; Natansohn, A. and Rochon, P., ‘Recent Developments in Aromatic Azo Polymers Research’, Chem. Mater., 5 (1993), pp.403-411.