Spectroscopic Properties of 2,2’-[Thiobis P- Phenylenenitrilomethylidyne ]Bis 4-Chloro/ Bromo/Methyl/Nitro/Methoxy Phenol

Yıl 2012, Cilt: 40 Sayı: 3, 213 - 218, 01.08.2012

Naki Çolak Volkan Kuşçu

Öz

Novel Schiff base has been synthesized from the reaction of 4,4’-diaminodiphenyl sulfide with 2-hydroxy- 5-substituebenzaldehyde and 2-hydroxynaphtaldehyde. The compounds were characterized by elemental analysis, FT-IR, 1H NMR,13C NMR. The UV-visible spectra of the compounds were studied in polar and nonpolar solvents in acidic and basic media. İt is point out that the enol-imine tautomer is dominant only in the solution form the compound 1a-e.

Anahtar Kelimeler

Schiff base, Diamine compounds, Benzaldehyde, Keto-enol tautomer

2,2’-[Tiyobis P-Fenilennitrilometilidin ]Bis 4-Kloro/ Bromo/Metil/Nitro/Metoksi Fenol'ün Spektroskopik Özellikleri

Öz

4’-diaminodifenil sülfit ile 2-hidroksi-5-sübstitüebenzaldehit ve 2-hidroksinaftaldehitin tepkimesi ile yeni Schiff bazları sentezlendi. Bileşiklerin yapıları elementel analiz, FT-IR, 1H NMR, 13C NMR ile aydınlatıldı. Bileşiklerin polar ve apolar çözücülerdeki asidik ve bazik ortamlardaki UV-vis. spektrumları incelendi. UV-vis. sonuçlarına göre çözücü ortamında enol-imin tautomerinin daha baskın olduğu görüldü

Anahtar Kelimeler

Schiff bazı, Daimin bileşikleri, Benzaldehit, Keto-enol tautomer

Kaynakça

• 1. GY. Yeap et al, Synthesis, crystal structure and spectroscopic study of para substituted 2-hydroxy3-methoxybenzalideneanilines, J. Mol. Struct., 658 (2003) 87.
• 2. AD. Garnovskii, AL. Nivorozhkin, VI. Minkin, Ligand environment and the structure of Schiff base adducts and tetracoordinated metal-chelates, Coord. Chem. Rev., 126 (1993) 1.
• 3. A. Elmali, M. Kabak, E. Kavlakoglu, Y. Elerman, TN Durlu, Tautomeric properties, conformations and structure of N-(2-hydroxy-5-chlorophenyl) salicylaldimine, J. Mol. Struct., 510 (1999) 207.
• 4. H. Temel, S. Ilhan, M. Sekerci, R. Ziyadanogullari, The synthesis and spectral characterization of new Cu(II), Ni(II), Co(III), and Zn(II) complexes with Schiff base, Spectrosc. Lett., 35 (2002) 219.
• 5. GY. Yeap, SG. Teoh, SB. Teo, SC. Loh, HK. Fun, Inner sphere complexes derived from the coordinate interactions of tin(IV) isothiocyanate moieties with 1-[(4-methylphenylimino)-methyl]-2-phenol. Crystal structure of diisothiocyanatodimethylbis {1-[(4-methylphenylimino)-methyl]-2-phenol} tin(IV), Me2Sn(NCS)2.[HOC6H4CH:NC6H4CH3]2, Poly-hedron, 15 (1996) 3941.
• 6. Z. Popovic, V. Roje, G. Pavlovic, DM. Calogovic, G. Giester, M. Rajic, Preparation and characterization of the 1:1 adducts of mercury(II) halides with N-benzyland N-p-tolyl-2-oxo-1-naphthylideneamine. The crystal and molecular structures of two isostructural di-m-halo-bis[halo(N-benzyl-2-oxo-1-naphthylideneamine)-mercury(II)] adducts (halo=chloro, bromo), Inorg. Chim. Acta, 322 (2001) 65.
• 7. Centore, R.; Roviello, A.; Sirigu, A Liguid-crystalline polymorphism in a class of low molar mass analogs of mesogenic polyesters. Liquid Crystals 3(11) (1988)1525.
• 8. SC. Bhatia, JM. Bindlish, AR. Saini, PC. Jain, J. Chem. Soc. Dalton Trans., Crystal and molecular structure of bis(N-allylsalicylideneiminoato)-nickel(II) andcopper(II) 9(1981)1773.
• 9. J. Costamagna, J. Vargas, R. Latorre, A. Alvarado, G. Mena, Coordination compounds of copper, nickel and iron with Schiff bases derived from hydroxynaphthaldehydes and salicylaldehydes Coord. Chem. Rev., 119 (1992) 67.
• 10. M. Yıldız, Z. Kılıc, T. Hokelek, Intramolecular hydrogen bonding and tautomerism in Schiff bases. Part I. Structure of 1,8-di[N-2-oxyphenyl-salicylidene]- 3,6-dioxaoctane J. Mol. Struct., 441 (1998) 1.
• 11. M. Gavranic´ , B. Kaitner, E. Meštrovic´ Intramolecular N−H...O hydrogen bonding, quinoid effect, and partial π-electron delocalization in N-aryl Schiff bases of 2-hydroxy-1-naphthaldehyde: the crystal structures of planar N-(α-naphthyl)- and N-(βnaphthyl)-2-oxy-1-naphthaldimine J. Chem. Crystallogr., 26 (1996) 23.
• 12. E. Hadjoudis, M. Vittorakis, IM. Mavridis, Photochromism and thermochromism of schiff bases in the solid state and in rigid glasses. Tetrahedron 43 (1987) 1345.
• 13. E. Hadjoudis, IM. Mavridis, Photochromism and thermochromism of Schiff bases in the solid state: structural aspects. Chem. Soc. Rev., 33 (2004) 579.
• 14. Fang WH, Zhang Y, You XZ. Theoretical Studies on Proton Transfer Processes of Schiff Bases. J. Mol. Struct. (Theochem), 334, (1995) 81.
• 15. JM. Fernandez-G, FR. Portilla, BQ. Garcia, RA. Toscano, R. Salcedo, The structures of some orthohydroxy Schiff base ligands. J. Mol.Struct., 561 (2001) 197.
• 16. I. Matanovic, N. Doslic, Infrared Spectroscopy of the Intramolecular Hydrogen Bond in Acethylacetone: A Computational Approach J. Phys. Chem. A, 109 (2005) 4185.
• 17. FS. Du, X. Zhang, GQ. Chen, ZC. Li, FM. Li, H. Pan, QY. Gao, J. Chem. Chin. Univ., Chin, 24 (2003) 374. İn this literature Xin Zhang, Zi-Chen Li, Chun-Feng Lao, De-Chun Zou, Feng-Zhu Lu, Guang-Qiang Chen, FuSheng Du, Fu-Mian Li, New β-diketone-containing styrenic monomers and their polymers: Synthesis, keto–enol tautomerism and related fluorescence behavior. Polymer. Vol. 47(10)(2006) 3390.
• 18. V. Tsaryuk, V. Zolin, J. Legendziewiez, R. Szostak, J. Sokolnicki, Effect of ligand radicals on vibrational IR, Raman and vibronic spectra of europium β-diketonates. Spectroc Acta Part A-Mol Biomol Spectr., 61 (2005) 185.
• 19. Bolvig, Simon; Hansen, Poul Erik Isotope effects on chemical shifts as an analytical tool in structural studies of intramolecular hydrogen bonded compounds. Current Organic Chemistry 4(1) (2000)19.
• 20. Raczynska, Ewa D.; Krygowski, Tadeusz M.; Zachara, Joanna E.; Osmialowski, Borys; Gawinecki, Ryszard Tautomeric equilibria, H-bonding and π-electron delocalization in o-nitrosophenol. A B3LYP/6- 311+G(2df,2p) study Journal of Physical Organic Chemistry , 18(8)(2005) 892
• 21. Abdollahi, Hamid; Mahdavi, Vahideh Tautomerization Equilibria in Aqueous Micellar Solutions: A Spectrophotometric and Factor-Analytical Study Langmuir 23(5)(2007)2362.
• 22. Cherlet, Marc; De Backer, Patrick; Croubels, Siska Control of the keto-enol tautomerism of chlortetracycline for its straightforward quantitation in pig tissues by liquid chromatography-electrospray ionization tandem mass spectrometry Journal of Chromatography, A 1133(1-2)(2006)135.
• 23. Gilli P, Bertolasi V, Pretto L, Ferretti V, Gilli G. Covalent versus electrostatic nature of the strong hydrogen bond: discrimination among single, double, and asymmetric single-well hydrogen bonds by variabletemperature X-ray crystallographic methods in beta-diketone enol RAHB systems. J Am Chem Soc., 126(2004)3845.
• 24. Gilli P, Bertolasi V, Ferretti V, Gilli G. Evidence for Intramolecular N−H•••O Resonance-Assisted Hydrogen Bonding in β-Enaminones and Related Heterodienes. A Combined Crystal-Structural, IR and NMR Spectroscopic, and Quantum-Mechanical Investigation. J Am Chem Soc., 122(2000)10405.
• 25. Kenar, James A. Preparation of long-chain β-enaminones and β-diketones from long-chain 3,5-disubstituted isoxazole compounds Journal of the American Oil Chemists’ Society 80(10), (2003), 1027-1032
• 26. M. Yıldız, Z. Kılıc, T. Hokelek, Intramolecular hydrogen bonding and tautomerism in Schiff bases. Part I. Structure of 1,8-di[N-2-oxyphenyl-salicylidene]- 3,6-dioxaoctane J. Mol. Struct., 1(1998)441.
• 27. Nazır, H., Yıldız, H., Yılmaz, M.N. Tahir, Ülkü, D., Intramolecular hydrogen bonding and tautomerism in Schiff bases. Structure of N-(2-pyridil)-2- oxo-1-naphthylidenemethylamine J. Mol.Struct., 524(2000)241.
• 28. Pohloudek-Fabini, R.; Friedrich, P. Organic thiocyanates. IX. Synthesis of 1-thiocyanato-2- isothiocyanatonaphthalene and some of its reaction products. Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 298(1)(1965)51.
• 29. Krasovitskii, B. M.; Mal’tseva, N. I. Azomethine bases. VIII. Azomethine bases-derivatives of aromatic diamines. Zhurnal Obshchei Khimii 2(5)(1966)894.