skip to main content

Synthesis, Structural Characterization of a New Ni(II) Complex and Its Catalytic Activity for Oxidation of Benzyl Alcohol

College of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, China

Received: 30 Mar 2022; Revised: 25 Apr 2022; Accepted: 26 Apr 2022; Available online: 6 May 2022; Published: 30 Jun 2022.
Editor(s): Istadi Istadi
Open Access Copyright (c) 2022 by Authors, Published by BCREC Group
Creative Commons License This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
Fulltext View|Download

Citation Format:
Cover Image
Abstract

In ethanol-water (v:v = 1:1), a new Ni(II) complex, [Ni(L)2(H2O)2] (1) (HL = 6-phenylpyridine-2-carboxylic acid) was synthesized using 6-phenylpyridine-2-carboxylic acid, NaOH and Ni(CH3COO)2.4H2O. The structure of complex 1 has been determined by elemental analysis and single crystal X-ray diffraction. The single crystal analysis shows that complex 1 contains one Ni(II) ion, two L ligands and  two coordinated water molecules. In 1, the Ni(II) ion is six-coordinated to two O atoms and two N atoms from L ligands and two O atoms from coordinated water molecules, respectively, which form a distorted octahedral coordination geometry. The whole unit of complex 1 is interconnected to each other through intermolecular N−H•••O hydrogen bonds involving oxygen atom of coordinated water molecule and the oxygen atoms of  L ligand to form 1D molecular architecture. The catalytic activity of complex 1 for oxidation of benzyl alcohol with O2 was investigated. The complex 1 shows good catalytic performance for the oxidation of benzyl alcohol, the benzyl alcohol conversion, benzaldehyde selectivity, and benzaldehyde yield were 49.1%, 92.0%, and 45.2%, respectively, at 90 °C under 0.7 Mpa O2 for 2 h. Moreover, complex 1 could be recovered easily by centrifugation and used repetitively for at least four times. Copyright © 2022 by Authors, Published by BCREC Group. This is an open access article under the CC BY-SA License (https://creativecommons.org/licenses/by-sa/4.0).

Keywords: 6-Phenylpyridine-2-carboxylic acid; Ni (II) complex; Synthesis; Single crystal structure; Catalytic activity
Funding: National Natural Science Foundation of China under contract No. 21171132; Science Foundation of Weiyuan Scholars Innovation Team

Article Metrics:

  1. Liang, Q.N., Chen, J.M., Wang, F.L., Li, Y.W. (2020). Transition Metal-based Metal-organic Frameworks for Oxygen Evolution Reaction. Coordination Chemistry Reviews, 424, 213488. DOI: 10.1016/j.ccr.2020.213488
  2. Wei, W.C., Liu, Z., Wei, R.Z., Liang, C.X., Feng, X.Z., Han, G.C. (2021). Synthesis, Crystal Structure and Anticorrosion Performance of Zn(II) and Ni(II) Complexes. Journal of Molecular Structure, 1228, 129452. DOI: 10.1016/j.molstruc.2020.129452
  3. Danuta, T., Wiktor, B., Karol, B., Michalina, K. (2021). Electrocatalytic Properties of Ni(II) Schiff Base Complex Polymer Films. Materials, 15, 191. DOI: 10.3390/ma15010191
  4. Li, R.F., Zhang, H., Hong, M.Z., Shi, J.G., Liu, X.F., Feng, X. (2022). Two Co(II)/Ni(II) Complexes Based on Nitrogenous Heterocyclic Ligands as High-performance Electrocatalysts for the Hydrogen Evolution Reaction. Dalton Transactions, 51, 3970–3976. DOI: 10.1039/D1DT03814A
  5. Reyes-Mata, C., Castillo, I. (2020). Calix[8]arene-based Ni(II) Complexes for Electrocatalytic CO2 Reduction. Inorganica Chimica Acta, 507, 119607. DOI: 10.1016/j.ica.2020.119607
  6. Kreškov, L., Miňo, A., Holub, M., Kuchr, J., Werner, A., Toms, M., Čižmr, E., Falvello, L., Černk, J. (2021). Heteroleptic Complexes of Ni(II) with 2,2’-Bipyridine and Benzoato Ligands. Magnetic Properties of [Ni(bpy)(Bz)2]. Inorganica Chimica Acta, 527, 120588. DOI: 10.1016/j.ica.2021.120588
  7. Shen, L.Y., Hu, P., Yang, X.J., Xu, H., Huang, Y.L., Redshaw, C., Zhang, Q.L. (2022). Structural and Magnetic Characterization of Tetranuclear [Ni(II)2Ln(III)2] Complexes Bearing Tetra-branched Schiff base Ligands. Polyhedron, 212, 115584. DOI: 10.1016/j.poly.2021.115584
  8. Khan, M.R., Niu, X.G., Chen, T.L., Liu, Y., Liu, Z.Y., Liu, B., Zhang, Y.X., Li, J.P. (2021). Structural Diversity and Magnetic Properties of Six Ferrocenyl Monocarboxylate Mn(II), Ni(II) and Co(II) Complexes with 1D Aqua, Carboxyl or Dinuclear Hydroxyl Bridges. CrystEngComm, 23, 3185–3195. DOI: 10.1039/D1CE00189B
  9. Kirthan, B.R., Prabhakara, M.C., Bhojyanaik, H.S., Amith Nayak, P.H., Viswanath, R., Teja, H.B. (2022). Optoelectronic, Photocatalytic, and DNA Interaction Studies of Synthesised Cu(II), Co(II), and Ni(II) Complexes Containing Schiff Base Ligand. Inorganic Chemistry Communications, 135, 109109. DOI: 10.1016/j.inoche.2021.109109
  10. Jana, K., Maity, R., Puschmann, H., Mitra, A., Ghosh, R., Debnath, S.C., Shukla, A., Mahanta, A.K., Maity, T., Samanta, B.C. (2021). A Binuclear Chloride Bridged Cu(II) and a Mononuclear Ni(II) Complex: Synthesis, Crystal structure, Photocatalytic and Biological Studies. Inorganica Chimica Acta, 515, 120067. DOI: 10.1016/j.ica.2020.120067
  11. Zhang, M.L., Bai, Y., Ren, Y.X., Wang, J.J., Yang, X.G., Ma, L.F. (2021). Structural Diversity and Photocatalytic Activity of Six Co(II)/Ni(II) Complexes with Three Flexible Phenylenediacetate Isomers. CrystEngComm, 23, 1616-1627. DOI: 10.1039/D0CE01702G
  12. El-Gammal, O.A.., Mohamed, F.S., Rezk, G.N., El-Bindary, A.A. (2021). Synthesis, Characterization, Catalytic, DNA Binding and Antibacterial Activities of Co(II), Ni(II) and Cu(II) Complexes with New Schiff Base Ligand. Journal of Molecular Liquids, 326, 115223. DOI: 10.1016/j.molliq.2020.115223
  13. Dey, L., Rabi, S., Palit, D., Hazari, S.K.S., Begum, Z.A., Rahman, I.M.M., Roy, T.G. (2021). Syntheses, Characterization, and Antimicrobial Studies of Ni(II), Cu(II), and Co(III) Complexes with an N-Pendant Azamacrocyclic Chelator. Journal of Molecular Structure, 1240, 130579. DOI: 10.1016/j.molstruc.2021.130579
  14. Badea, M., Grecu, M.N., Chifiriuc, M.C., Bleotu, C., Popa, M., Iorgulescu, E.E., Avram, S., Uivarosi, V., Munteanu, A.C., Ghica, D., Olar, R. (2021). Insight on Ni(II) and Cu(II) Complexes of Biguanide Derivatives Developed as Effective Antimicrobial and Antitumour Agents. Applied Organometallic Chemistry, 35, 1-17. DOI: 10.1002/aoc.6155
  15. Guo, S.Z., Wang, J.F., Feng, S.S., Zhao, L. (2021). Co(II) and Ni(II) Bis(salamo)-based Tetraoxime Complexes: Syntheses, Structural Characterizations, Fluorescence Properties, and Hirshfeld Analyses. Journal of Coordination Chemistry, 74, 1181–1195. DOI: 10.1080/00958972.2021.1891227
  16. Karaoğlan, G.K. (2022). Synthesis of New Schiff Base and Its Ni(II), Cu(II), Zn(II) and Co(II) Complexes; Photophysical, Fluorescence Quenching and Thermal Studies. Journal of Molecular Structure, 256, 132534. DOI: 10.1016/j.molstruc.2022.132534
  17. Youssef, H.M., Abdulhamed, Y.K., El-Reash, G.M.A., Yousef, T.A. (2022). Cr(III) and Ni(II) Complexes of Isatin-Hydrazone Ligand: Preparation, Characterization, DFT Studies, Biological Activity, and Ion-Flotation Separation of Ni(II). Inorganic Chemistry Communications, 138, 109278. DOI: 10.1016/j.inoche.2022.109278
  18. El-ghamry, M.A., Shebl, M., Saleh, A.A., Khalil, S.M.E., Dawy, M., Ali, A.A.M. (2022). Spectroscopic Characterization of Cu(II), Ni(II), Co(II) Complexes, and Nano Copper Complex Bearing a New S, O, N-donor Chelating Ligand. 3D Modeling Studies, Antimicrobial, Antitumor, and Aatalytic Activities. Journal of Molecular Structure, 1249, 131587. DOI: 10.1016/j.molstruc.2021.131587
  19. Yan, J., Wang, Y.B., Hou, S.Y., Shi, L.L., Zhu, X.J., Hao, X.Q., Song, M.P. (2020). NCC Pincer Ni (II) Complexes Catalyzed Hydrophosphination of Nitroalkenes with Diphenylphosphine. Applied Organometallic Chemistry, 34, 1-6. DOI: 10.1002/aoc.5954
  20. Venkatesh, S., Panicker, R.R., Lenin Kumar, V., Pavankumar, B.B., Viswanath, N., Singh, S., Desikan, R., Sivaramakrishna, A. (2020). Efficient Catalytic Transfer Hydrogenation Reactions of Carbonyl Compounds by Ni(II)-Diphosphine Complexes. Journal of Coordination Chemistry, 73, 2963−2977. DOI: 10.1080/00958972.2020.1837784
  21. Sankaralingam, M., Balamurugan, M., Palaniandavar, M. (2020). Alkane and Alkene Oxidation Reactions Catalyzed by Nickel(II) Complexes: Effect of Ligand Factors. Coordination Chemistry Reviews, 403, 213085. DOI: 10.1016/j.ccr.2019.213085
  22. Tuskaev, V.A., Zubkevich, S.V., Saracheno, D., Gagieva, S.C., Dorovatovskii, P.V., Kononova, E.G., Khrustalev, V.N., Zarubin, D.N., Bulychev, B.M., Kissin, Y.V. (2019). Nickel(II) Complexes with Tripodal NNN Ligands as Homogenous and Supported Catalysts for Ethylene Oligomerization. Molecular Catalysis, 464, 29–38. DOI: 10.1016/j.mcat.2018.12.018
  23. Xavier, K.O., Chacko, J., Yusuff, K.K.M. (2004). Zeolite-encapsulated Co(II), Ni(II) and Cu(II) Complexes as Catalysts for Partial Oxidation of Benzyl Alcohol and Ethylbenzene. Applied Catalysis A: General, 258, 251–259. DOI: 10.1016/j.apcata.2003.09.027
  24. Thamilarasan, V., Revathi, P., Praveena, A., Kim, J., Chandramohan, V., Sengottuvelan, N. (2020). Synthesis and Characterization of Dimeric Schiffff base CoII, NiII, CuII Complexes for Their Catalytic Application of Aerobic Oxidation of Alcohol and Interaction with Biomolecules. Inorganica Chimica Acta, 508, 119626–119632. DOI: 10.1016/j.ica.2020.119626
  25. Mobinikhaledi, A., Zendehdel, M., Safari, P. (2013). Synthesis and Characterization of Some Novel Transition Metal Schiff base Complexes Encapsulated in Zeolite Y: Effective Catalysts for the Selective Oxidation of Benzyl Alcohol. Reaction Kinetics Mechanisms and Catalysis, 110, 497–514. DOI: 10.1007/s11144-013-0609-7
  26. Lin, S., Wu, D., Tang, E., Yan, G., Yang, M., Xu, W. (2008). A Polymeric Chain Formed by Bicapped Pseudo-Keggin Polyoxometalate and [Ni(en)2]2+ Complexes: Synthesis, Structure and Catalytic Properties of {[H3PMo8V6O46][Ni(en)2]}·2[Ni(en)2]·5H2O. Journal of Coordination Chemistry, 61, 167–177. DOI: 10.1080/00958970701317220
  27. Hasanpour, R., Feizpour, F., Jafarpour, M., Rezaeifard, A. (2018). Nickel(II) Riboflavin Complex as an Efficient Nanobiocatalyst for Heterogeneous and Sustainable Oxidation of Benzylic Alcohols and Sulfides. New Journal of Chemistry, 42, 7383–7391. DOI: 10.1039/C8NJ00281A
  28. Tai, X.S., Zhou, X.J., Liu, L.L. (2019). Synthesis, Crystal Structure and Antitumor Activity of a Na(I) Coordination Polymer Based on 2-Propyl-4,5-imidazoledicarboxylic Acid and 1,10-Phenanthroline Ligands. Chinese Journal of Structural Chemistry, 38, 1079–1085. DOI: 10.14102/j.cnki.0254-5861.2011-2232
  29. Wang, L.H., Liang, L., Tai, X.S. (2020). The Crystal Structure 2,2’-Bipyridine-κ2N,N’-(2-(3-amino-4-chlorobenzoyl)benzoato-κ1O)-(2-(3-amino-4-chlorobenzoyl)benzoato-κ1O,O’)zinc(II) -ethanol (1/1), C40H32Cl2N4O7Zn. Zeitschrift für Kristallographie. New Crystal Structures, 235, 1281–1283. DOI: 10.1515/ncrs-2020-0261
  30. Wang, L.H., Wang, Z.J., Zhao, M.L., Tai, X.S., Ouyang, J., Li, Y.F., Zhang, W., Jia, W.L. (2021). Synthesis, Crystal Structure of Tetra-Nuclear Macrocyclic Zn (II) Complex and Its Application as Catalyst for Oxidation of Benzyl Alcohol. Bulletin of Chemical Reaction Engineering & Catalysis, 16, 839–846. DOI: 10.9767/bcrec.16.4.10978.839-846
  31. Tai, X.S., Xia, Y.P. (2022). The Crystal Structure of [(2,2’-Bipyridine-κ2 N,N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co. Zeitschrift für Kristallographie. New Crystal Structures, 237, 225–227. DOI: 10.1515/ncrs-2021-0473
  32. Tai, X.S., Liang, L., Li, X.T., Cao, S.H., Wang, L.H. (2021). Crystal Structure of Diaqua-bis(μ2-6-phenylpyridine-2-carboxylate-κ3N,O:O)-bis(6-phenylpyridine-2-carboxylato-κ2N,O)lead(II)-N,N-dimethylformamide-water (1/2/4), C54H58N6O16Pb2. Zeitschrift für Kristallographie. New Crystal Structures, 236, 1199–1201. DOI: 10.1515/ncrs-2021-0277
  33. Tai, X.S., Wang, Z.J., Ouyang, J., Li, Y.F., Zhang, W., Jia, W.L., Wang, L.H. (2021). The Crystal Structure of [(Phenantroline-κ2N,N’)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)cobalt(II)]monohydrate, C36H26N4O5Co. Zeitschrift für Kristallographie. New Crystal Structures, 236, 1309–1311. DOI: 10.1515/ncrs-2021-0319
  34. Wang, L.H., Tai, X.S., Xia, Y.P. (2022). The Crystal Structure of Catena-poly[(m2-4,4′-bipyridine-κ2N:N)-bis(6-phenylpyridine-2-carboxylato-κ2N,O) zinc(II)], C34H24N4O4Zn. Zeitschrift für Kristallographie. New Crystal Structures, 237, 305–307. DOI: 10.1515/ncrs-2022-0003
  35. Feng, Y.M., Tai, X.S., Xia, Y.P. (2022). The crystal structure of [(2,2’-bipyridine-κ2N,N)-bis(6-phenylpyridine-2-carboxylate-κ2N,O)copper(II)], C34H24N4O4Cu. Zeitschrift für Kristallographie. New Crystal Structures, 237, 285-287. DOI: 10.1515/ncrs-2021-0486
  36. Sheldrick, G.M. (2015). Crystal Structure Refinement with SHELXL. Acta Crystallographica, C71, 3–8. DOI: 10.1107/S2053229614024218
  37. Sheldrick, G.M. (2015). SHELXT-Integrated space-group and crystal-structure determination. Acta Crystallographica, A71, 3–8. DOI: 10.1107/S2053273314026370
  38. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., Puschmann, H. (2009). OLEX2: A Complete Structure Solution, Refinement and Analysis Program. Journal of Applied Crystallography, 42, 339–341. DOI: 10.1107/S0021889808042726
  39. Tai, X.S., Li, P.F., Liu, L.L. (2018). Synthesis, Crystal Structure and Catalytic Activity of a Calcuim(II) Complex with 4-Formylbenzene-1,3-disulfonate-isonicotinic Acid Hydrazone. Bulletin of Chemical Reaction Engineering & Catalysis, 13, 429–435. DOI: 10.9767/bcrec.13.3.1961.429-435

Last update:

No citation recorded.

Last update:

No citation recorded.