Hilal KIRPIK, Muhammet KÖSE, Muharrem KARABÖRK, Koray SAYIN

New diazo-containing phenolic oximes: structural characterization, computational studies, and solvent extraction of Cu(II), Ni(II), and Zn(II) ions

In the current study, four new phenolic oxime ligands (HL1ox–HL4ox) containing diazo groups (-N=N-) weresynthesized and used for liquid-liquid extraction of heavy metal ions [Cu(II), Ni(II), and Zn(II)]. The new compoundswere characterized by analytical and spectroscopic methods. Solid-state structures of HL1ox–HL3ox were determinedby single-crystal X-ray diffraction studies. Hirshfeld surface analysis of the compounds was performed to determine thecontribution of different intermolecular contacts to the stability of the structures. The HL1ox–HL4ox ligands showedhigher extraction performance for Cu(II) ion than Ni(II) and Zn(II) ions. The effect of pH on extraction capacity wasinvestigated and the oxime compounds showed high extraction capacity at low pH values. The effects of the substitutegroups (at the meta position of the phenol ring) on the extraction were investigated. Within the oxime ligands, theHL3ox compound exhibited higher extraction capacity for Cu(II) ions. The better extraction value of HL3ox is attributedto the weak hydrogen bond type interactions, which result in more stable complexes.

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1. Wilson, A. M.; Bailey, P. J.; Tasker, P. A.; Turkington, J. R.; Grant, R. A.; Love, J. B. Chem. Soc. Rev. 2014, 43, 123-134.
2. Habashi, F. Hydrometallurgy 2005, 79, 15-22.
3. Flett, D. S. J. Chem. Technol. Biotechnol. 1999, 74, 99-105.
4. Mézard, M.; Parisi, G.; Virasoro, M. Spin Glass Theory and Beyond; World Scientific Publishing Company: Singapore, 1987.
5. Tasker, P. A.; Tong, C. C.; Westra, A. N. Coord. Chem. Rev. 2007, 251, 1868-1877.
6. Turkington, J. R.; Bailey, P. J.; Love, J. B.; Wilson, A. M.; Tasker, P. A. Chem. Comm. 2013, 49, 1891-1899.
7. Kordosky, G. A. J. South African Inst. Min. 2002, 102, 445-450.
8. Moore, R. H.; Partridge, J. A. Batelle Pacific Northwest Laboratories Report (No. BNWL-SA-4476; CONF-721214- 1); Pacific Northwest Laboratories: Batelle, WA, USA, 1972.
9. Zhu, S.; Hu, H.; Hu, J.; Li, J.; Hu, F.; Wang, Y. J. Mol. Struc. 2017, 1144, 191-198.
10. Smith, A. G.; Tasker, P. A.; White, D. J. Coord. Chem. Rev. 2003, 241, 61-85.
11. Forgan, R. S.; Wood, P. A.; Campbell, J.; Henderson, D. K.; McAllister, F. E.; Parsons, S.; Pidcock, E.; Swart, R. B.; Tasker, P. A. Chem. Commun. 2007, 46, 4940-4942.
12. Hoang, A. S.; Tran, T. H.; Nguyen, H. N.; Vu, H. S.; Vo, T. P.; Phan, C.; Nguyen, T. V. Korean J. Chem. Eng. 2015, 32, 1598-1605.
13. Manimekalai, A.; Balachander, R. J. Mol. Struc. 2012, 1027, 175-185.
14. Premuzic, D.; Filarowski, A.; Hołyńska, M. J. Mol. Struc. 2017, 1136, 100-106.
15. Spackman, M. A.; Jayatilaka, D. Cryst. Eng. Comm. 2009, 11, 19-32.
16. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chemie Int. Ed. Eng. 1995, 34, 1555-1573.
17. Forgan, R. S. Inorg. Chem. 2011, 50, 4515-4522.
18. Roach, B. D. Aust. J. Chem. 2017, 70, 556-565.
19. Eren, T.; Kose, M.; Sayin, K.; McKee, V.; Kurtoglu, M. J. Mol. Struct. 2014, 1065, 191-198.
20. Cabir, B.; Avar, B.; Gülcan, M.; Kayraldız, A.; Kurtoğlu, M. Turk. J. Chem. 2013, 37, 422-438.
21. Köse, M.; Kurtoglu, N.; Gümüşsu, Ö.; Tutak, M.; McKee, V.; Karakaş, D.; Kurtoglu, M. J. Mol. Struct. 2013, 1053, 89-99.
22. Bitmez, Ş.; Sayin, K., Avar, B.; Köse, M.; Kayraldız, A.; Kurtoğlu, M. J. Mol. Struct. 2014, 1076, 213-226.
23. Bruker Inc. APEX2 and SAINT. Bruker AXS Inc.: Madison, WI, USA, 1998.
24. Bruker Inc. A. P. E. X. Saint and SADABS. Bruker Inc.: Madison, WI, USA, 2009.
25. Sheldrick, G. M. Acta Crystallogr. Sect. A Found. Crystallogr. 2008, 64, 112-122.
26. Sheldrick, G. M. Acta Crystallogr. Sect. C Struct. Chem. 2015, 71, 3-8.
27. Dennington, R.; Keith, T.; Millam, J. Gauss View; Semichem Inc.: Shawnee Mission, KS, USA, 2009.
28. Frisch, M. J. Gaussian 09 Revision D. 01; Gaussian Inc.: Wallingford, CT, USA, 2009.
29. Zhurko, G. A.; Zhurko, D. A. ChemCraft 1.8, 2009.