Citation: Wu-Jiu JIANG, Peng-Hui NI, Fang-Fang MAO, Yu-Xing TAN. Syntheses, Crystal Structures and Property of Pyridine Zinc(Ⅱ) Complexes Based on Halogenated Salicylaldehyde Schiff Base[J]. Chinese Journal of Structural Chemistry, ;2022, 41(3): 220301. doi: 10.14102/j.cnki.0254-5861.2011-3285 shu

Syntheses, Crystal Structures and Property of Pyridine Zinc(Ⅱ) Complexes Based on Halogenated Salicylaldehyde Schiff Base

Key Laboratory of Functional Metal-organic Compounds of Hunan Province, Key Laboratory of Organometallic New Materials, College of Hunan Province, Hunan Provincial Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the Upper Reaches of Xiangjiang River, College of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421008, China

Corresponding author: Yu-Xing TAN, xulichem@ujs.edu.cn
Received Date: 11 June 2021
Accepted Date: 31 August 2021

Fund Project: the Scientific Research Fund of Hunan Provincial Education Department of China 19C0279

Figures(6)

Schiff base pyridine zinc(Ⅱ) complexes 1~4 were synthesized by the reaction of the 2-((2-hydroxybenzylidene)amino)phenol Schiff base with appended donor functionality, zinc acetate, and pyridine. The results of the structural characterization of the complex show that they have the same coordination mode and similar steric structure. Complexes 1 and 3 form a one-dimensional chain structure and two-dimensional grid structure by lots of hydrogen bonds, respectively. Thermogravimetric analysis shows complexes 1~4 can exist stably below 150 ℃. The results of the fluorescence quenching experiments between the complexes and DNA-EB show that the interaction between them is intercalation, and the effect of complex 1 is the most obvious. It is speculated that the steric hindrance of complex 1 is relatively small, and the aromatic ring on the ligand is more likely to inserted into the base pair of DNA.
- zinc complex,
- Schiff base,
- synthesis,
- crystal structure,
- property
1. [1]
  Stefanidou, M.; Maravelias, C.; Dona, A.; Spiliopoulou, C. Zinc: a multipurpose trace element. Arch. Toxicol. 2006, 80, 1–9. doi: 10.1007/s00204-005-0009-5
2. [2]
  Chasapis, C. T.; Loutsidou, A. C.; Spiliopoulou, C. A.; Stefanidou, M. E. Zinc and human health: an update. Arch. Toxicol. 2012, 86, 521–534. doi: 10.1007/s00204-011-0775-1
3. [3]
  Han, A. Y.; Su, H.; Xu, G. H.; Khan, M. A.; Li, H. Synthesis, crystal structures, and luminescent properties of Zn(Ⅱ), Cd(Ⅱ), Eu(Ⅲ) complexes and detection of Fe(Ⅲ) ions based on a diacylhydrazone Schiff base. RSC Adv. 2020, 10, 23372–23378. doi: 10.1039/D0RA03642K
4. [4]
  Ríos Gómez, M. L.; Lampronti, G. I.; Yang, Y.; Mauro, J. C.; Bennett, T. D. Relating structural disorder and melting in complex mixed ligand zeolitic imidazolate framework glasses. Dalton T. 2020, 49, 850–857. doi: 10.1039/C9DT03559A
5. [5]
  Guo, K.; Wang, P.; Tan, W.; Li, Y.; Gao, X.; Wang, Q.; Pu, L. Structure of a dimeric BINOL-imine-Zn(Ⅱ) complex and its role in enantioselective fluorescent recognition. Inorg. Chem. 2020, 59, 17992–17998. doi: 10.1021/acs.inorgchem.0c02330
6. [6]
  Jedrzejas, M. J.; Setlow, P. Comparison of the binuclear metalloenzymes diphosphoglycerate-independent phosphoglycerate mutase and alkaline phosphatase: their mechanism of catalysis via a phosphoserine intermediate. Chem. Rev. 2001, 101, 607–618. doi: 10.1021/cr000253a
7. [7]
  Lipscomb, W. N.; Sträter, N. Recent advances in zinc enzymology. Chem. Rev. 1996, 96, 2375–2434. doi: 10.1021/cr950042j
8. [8]
  Sanatkar, T. H.; Khorshidi, A.; Janczak, J. Dinuclear Zn(Ⅱ) and tetranuclear Co(Ⅱ) complexes of a tetradentate N₂O₂ Schiff base ligand: synthesis, crystal structure, characterization, DFT studies, cytotoxicity evaluation, and catalytic activity toward benzyl alcohol oxidation. Appl. Organomet. Chem. 2020, 34, e5493.
9. [9]
  Huang, H. S.; Zhang, T. L.; Zhang, S. T.; Zhang, J. G.; Wu, X. F.; Xu, J. H. Theoretical study of the structure, mechanism of detonation initiation and stability of transition metal carbohydrazide nitrates. Chin. J. Struct. Chem. 2013, 32, 1491-1496.
10. [10]
  Opalade, A. A.; Karmakar, A.; Rúbio, G. M. D. M.; Pombeiro, A. J. L.; Gerasimchuk, N. Zinc complexes with cyanoxime: structural, spectroscopic, and catalysis studies in the pivaloylcyanoxime–Zn system. Inorg. Chem. 2017, 56, 13962–13974. doi: 10.1021/acs.inorgchem.7b01891
11. [11]
  Mohamed, M. F.; Brown, R. S. Cleavage of an RNA model catalyzed by dinuclear Zn(Ⅱ) complexes containing rate-accelerating pendants. Comparison of the catalytic benefits of H-bonding and hydrophobic substituents. J. Org. Chem. 2010, 75, 8471–8477. doi: 10.1021/jo1017316
12. [12]
  Pandey, R.; Kumar, A.; Xu, Q.; Pandey, D. S. Zinc(Ⅱ), copper(Ⅱ) and cadmium(Ⅱ) complexes as fluorescent chemosensors for cations. Dalton T. 2020, 49, 542–568. doi: 10.1039/C9DT03017D
13. [13]
  Bazany-Rodríguez, I. J.; Salomón-Flores, M. K.; Viviano-Posadas, A. O.; García-Eleno, M. A.; Barroso-Flores, J.; Martínez-Otero, D.; Dorazco-González, A. Chemosensing of neurotransmitters with selectivity and naked eye detection of l-DOPA based on fluorescent Zn(Ⅱ)-terpyridine bearing boronic acid complexes. Dalton T. 2021, 50, 4255–4269. doi: 10.1039/D0DT04228E
14. [14]
  Mikata, Y.; Yamashita, A.; Kawamura, A.; Konno, H.; Miyamoto, Y.; Tamotsu, S. Bisquinoline-based fluorescent zinc sensors. Dalton T. 2009, 3800–3806.
15. [15]
  Majumdar, D.; Das, D.; Sreejith, S. S.; Das, S.; Kumar Biswas, J.; Mondal, M.; Ghosh, D.; Bankura, K.; Mishra, D. Dicyanamide-interlaced assembly of Zn(Ⅱ)-Schiff-base complexes derived from salicylaldimino type compartmental ligands: syntheses, crystal structures, FMO, ESP, TD-DFT, fluorescence lifetime, in vitro antibacterial and anti-biofilm properties. Inorg. Chim. Acta 2019, 489, 244–254. doi: 10.1016/j.ica.2019.02.022
16. [16]
  Martínez, V. R.; Aguirre, M. V.; Todaro, J. S.; Ferrer, E. G.; Williams, P. A. M. Candesartan and valsartan Zn(Ⅱ) complexes as inducing agents of reductive stress: mitochondrial dysfunction and apoptosis. New J. Chem. 2021, 45, 939–951. doi: 10.1039/D0NJ02937H
17. [17]
  Aleshin, G. Y.; Egorova, B. V.; Priselkova, A. B.; Zamurueva, L. S.; Khabirova, S. Y.; Zubenko, A. D.; Karnoukhova, V. A.; Fedorova, O. A.; Kalmykov, S. N. Zinc and copper complexes with azacrown ethers and their comparative stability in vitro and in vivo. Dalton T. 2020, 49, 6249–6258. doi: 10.1039/D0DT00645A
18. [18]
  Sheldrick, G. M. SHELXL-97, A Program for Crystal Structure Refinement. Germany Geöttingen: University of Geöttingen 1997.
19. [19]
  Wang, M.; Yu, F.; Jiang, W. J.; Tan, Y. X.; Zhang, F. X.; Kuang, D. Z. Syntheses, crystal structures and biological activity of the diorganotin 2-(2-(4-methoxybenzoyl)hydrazono)-3-phenylpropanoic carboxylate complexes. Chin. J. Struct. Chem. 2020, 39, 1965-1972.
20. [20]
  Zhang, S. Z.; Guo, G.; Ding, W. M.; Li, J.; Wu, Y.; Zhang, H. J.; Guo, J. Q.; Sun, Y. X. Synthesis and spectroscopic properties of two different structural Schiff base Zn(Ⅱ) complexes constructed with/without auxiliary ligands. J. Mol. Struct. 2021, 1230, 129627. doi: 10.1016/j.molstruc.2020.129627
21. [21]
  Uddin, M. N.; Ferdous, T.; Islam, Z.; Jahan, M. S.; Quaiyyum, M. A. Development of chemometric model for characterization of non-wood by FT-NIR data. J. Bioresour. Bioprod. 2020, 5, 196–203. doi: 10.1016/j.jobab.2020.07.005
22. [22]
  Chen, S.; Jiang, S.; Jiang, H. A review on conversion of crayfish-shell derivatives to functional materials and their environmental applications. J. Bioresour. Bioprod. 2020, 5, 238–247. doi: 10.1016/j.jobab.2020.10.002
23. [23]
  Cao, Y.; Wang, X. Z.; Li, Y. J.; Shen, D. H.; Dai, Y. P.; Zhang, S. Z.; Zhang, W. G. Effect of high temperature oil heat treatment on the stsrch content and mold-resistant property of bamboo. J. For. Eng. 2020, 5, 109–115.
24. [24]
  Chen, Z. J.; Gao, H.; Li, W.; Li, S. J.; Liu, S. X.; Li, J. Research progree of biomass-based optical materials. J. For. Eng. 2020, 5, 1–12. doi: 10.31186/jenggano.5.1.1-10
25. [25]
  Pretsch, E.; Bühlmann, P.; Badertscher, M. Structure Determination of Organic Compounds. Fourth ed. Berlin Heidelberg: Springer-Verlag 2009, p69-242.
26. [26]
  Ashok, B.; Hariram, N.; Siengchin, S.; Rajulu, A. V. Modification of tamarind fruit shell powder with in situ generated copper nanoparticles by single step hydrothermal method. J. Bioresour. Bioprod. 2020, 5, 180–185. doi: 10.1016/j.jobab.2020.07.003
27. [27]
  Tan, W.; Hao, X. L.; Wang, Q. W.; Ou, R. X. Mechanical and thermal properties of bamboo plastic composites reinforced by thermotropic liquid crystal copolyesters. J. For. Eng. 2020, 5, 97–103.
28. [28]
  Zheng, C. X.; Zhu, S.; Lu, Y.; Mei, C. T.; Xu, X. W.; Yue, Y. Y.; Han. J. Q. Synthesis and characterization of cellulose nanofibers/polyacrylic acid-polyacrylamide double network electroconductive hydrogel. J. For. Eng. 2020, 5, 93–100.
29. [29]
  Zhu, L. T.; Gu, Y. F.; Wu, G. S. Biomass thermal conductivity measurement system design. J. For. Eng. 2020, 5, 97–102.
30. [30]
  Yan, C.; Zhang, J.; Liang, T.; Li, Q. Diorganotin (Ⅳ) complexes with 4-nitro-N-phthaloyl-glycine: synthesis, characterization, antitumor activity and DNA-binding studies. Biomed. Pharmacother. 2015, 71, 119–127. doi: 10.1016/j.biopha.2015.02.027
31. [31]
  Daryanavard, M.; Jannesari, Z.; Javeri, M.; Abyar, F. A new mononuclear zinc(Ⅱ) complex: crystal structure, DNA- and BSA-binding, and molecular modeling; in vitro cytotoxicity of the Zn(Ⅱ) complex and its nanocomplex. Spectrochim. Acta A 2020, 233, 118175. doi: 10.1016/j.saa.2020.118175
32. [32]
  Mondal, A. S.; Jana, M. S.; Manna, C. K.; Naskar, R.; Mondal, T. K. Synthesis of a zinc(Ⅱ) complex with hexadentate N4S2 donor thioether ligand: X-ray structure, DNA binding study and DFT computation. J. Mol. Struct. 2018, 1164, 94–99. doi: 10.1016/j.molstruc.2018.03.038
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