Halogen Bonding in the Decoration of Secondary Coordination Sphere of Zinc(II) and Cadmium(II) Complexes: Catalytic Application in Cycloaddition Reaction of CO with Epoxides

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2023 Nov 29

PMID 38024759

Authors

Vusala A Aliyeva

Ana B Paninho

Ana V M Nunes

Anirban Karmakar

Atash V Gurbanov

Arianna R Rutigliano

Emma Gallo

Kamran T Mahmudov

Armando J L Pombeiro

Affiliations

Soon will be listed here.

Abstract

Three new zinc(II) complexes [Zn(HL)(HO)] (), [Zn(HL)(HO)] () (HL = 2,4-diiodo-5-(2-(2,4,6-trioxotetrahydropyrimidin-5(2)-ylidene)hydrazineyl)isophthalate) and [Zn(HL)(DMF)(HO)] () were synthesized by the reaction of Zn(II) salts with 5-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl) isophthalic acid (HL), 2,4,6-triiodo-5-(2-(2,4,6-trioxotetrahydropyrimidin-5(2)-ylidene)hydrazineyl) isophthalic acid (HL) (in the presence of NHOH·HCl) and 5-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)-2,4,6-triiodoisophthalic acid (HL), respectively. According to the X-ray structural analysis, the intramolecular resonance-assisted hydrogen bond ring remains intact, with NO distances of 2.562(5) and 2.573(5) Å in , 2.603(6) Å in , and 2.563(8) Å in . In the crystal packing of , the cooperation of IO and II types of halogen bonds between tectons leads to a one-dimensional supramolecular polymer, while IO interactions aggregate 1D chains of coordination polymer . These new complexes (, , and ) and known [Zn(HL)(HO)] () (HL = 5-(2-(2,4,6-trioxotetrahydropyrimidin-5(2)-ylidene) hydrazineyl)isophthalate), {[Zn(HL)(HO)]·3HO} (), [Cd(HL)(HO)] (), {[Cd(HL)(HO)(DMF)]·HO} (), [Cd(HL)] (), {[Cd(μ-HO)(μ-HL)(HL)]·2HO} (), and {[Cd(HL)(HO)]·4HO} () were tested as catalysts in the cycloaddition reaction of CO with epoxides in the presence of tetrabutylammonium halides as the cocatalyst. The halogen-bonded catalyst is the most efficient one in the presence of tetrabutylammonium bromide by affording a high yield (85-99%) of cyclic carbonates under solvent-free conditions after 48 h at 40 bar and 80 °C.

References

Zhang Y, Yang G, Xie R, Yang L, Li B, Wu G . Scalable, Durable, and Recyclable Metal-Free Catalysts for Highly Efficient Conversion of CO to Cyclic Carbonates. Angew Chem Int Ed Engl. 2020; 59(51):23291-23298. DOI: 10.1002/anie.202010651. View

Adolph M, Zevaco T, Altesleben C, Walter O, Dinjus E . New cobalt, iron and chromium catalysts based on easy-to-handle N4-chelating ligands for the coupling reaction of epoxides with CO2. Dalton Trans. 2013; 43(8):3285-96. DOI: 10.1039/c3dt53084a. View

Bai S, De Smet G, Liao Y, Sun R, Zhou C, Beller M . Homogeneous and heterogeneous catalysts for hydrogenation of CO to methanol under mild conditions. Chem Soc Rev. 2021; 50(7):4259-4298. DOI: 10.1039/d0cs01331e. View

Guo F, Zhang X . Metal-organic frameworks for the energy-related conversion of CO into cyclic carbonates. Dalton Trans. 2020; 49(29):9935-9947. DOI: 10.1039/d0dt01516d. View

Cabrera D, Lewis R, Diez-Poza C, Alvarez-Miguel L, Mosquera M, Hamilton A . Group 13 salphen compounds (In, Ga and Al): a comparison of their structural features and activities as catalysts for cyclic carbonate synthesis. Dalton Trans. 2023; 52(18):5882-5894. DOI: 10.1039/d3dt00089c. View

Xu K . Nonaqueous liquid electrolytes for lithium-based rechargeable batteries. Chem Rev. 2005; 104(10):4303-417. DOI: 10.1021/cr030203g. View

Li W, Wang H, Jiang X, Zhu J, Liu Z, Guo X . A short review of recent advances in CO hydrogenation to hydrocarbons over heterogeneous catalysts. RSC Adv. 2022; 8(14):7651-7669. PMC: 9078493. DOI: 10.1039/c7ra13546g. View

Perathoner S, Van Geem K, Marin G, Centi G . Reuse of CO in energy intensive process industries. Chem Commun (Camb). 2021; 57(84):10967-10982. DOI: 10.1039/d1cc03154f. View

Gurbanov A, Kuznetsov M, Karmakar A, Aliyeva V, Mahmudov K, Pombeiro A . Halogen bonding in cadmium(II) MOFs: its influence on the structure and on the nitroaldol reaction in aqueous medium. Dalton Trans. 2021; 51(3):1019-1031. DOI: 10.1039/d1dt03755b. View

10.

Guo W, Gomez J, Cristofol A, Xie J, Kleij A . Catalytic Transformations of Functionalized Cyclic Organic Carbonates. Angew Chem Int Ed Engl. 2018; 57(42):13735-13747. DOI: 10.1002/anie.201805009. View

11.

Yang L, Powell D, Houser R . Structural variation in copper(I) complexes with pyridylmethylamide ligands: structural analysis with a new four-coordinate geometry index, tau4. Dalton Trans. 2007; (9):955-64. DOI: 10.1039/b617136b. View

12.

Grabowski S . Tetrel bond-σ-hole bond as a preliminary stage of the SN2 reaction. Phys Chem Chem Phys. 2013; 16(5):1824-34. DOI: 10.1039/c3cp53369g. View

13.

Xu J, Peng S, Shi Y, Ding S, Yang G, Yang Y . A novel zirconium-based metal-organic framework covalently modified by methyl pyridinium bromide for mild and co-catalyst free conversion of CO to cyclic carbonates. Dalton Trans. 2022; 52(3):659-667. DOI: 10.1039/d2dt03507c. View

14.

Li C, Su Y, Lin C, Huang H, Tsai C, Lee T . Synthesis and characterization of trimetallic cobalt, zinc and nickel complexes containing amine-bis(benzotriazole phenolate) ligands: efficient catalysts for coupling of carbon dioxide with epoxides. Dalton Trans. 2017; 46(44):15399-15406. DOI: 10.1039/c7dt02841e. View

15.

Li Y, Liu S, Zhao X, Wang Y, Liu J, Wang X . CO-based amphiphilic polycarbonate micelles enable a reliable and efficient platform for tumor imaging. Theranostics. 2017; 7(19):4689-4698. PMC: 5706092. DOI: 10.7150/thno.21672. View

16.

Liu Q, Wu L, Jackstell R, Beller M . Using carbon dioxide as a building block in organic synthesis. Nat Commun. 2015; 6:5933. DOI: 10.1038/ncomms6933. View

17.

Fernandes D, Peixoto A, Freire C . Nitrogen-doped metal-free carbon catalysts for (electro)chemical CO conversion and valorisation. Dalton Trans. 2019; 48(36):13508-13528. DOI: 10.1039/c9dt01691k. View

18.

Hughes D, Delori A, Rehman A, Jones W . Using crystallography, topology and graph set analysis for the description of the hydrogen bond network of triamterene: a rational approach to solid form selection. Chem Cent J. 2017; 11(1):63. PMC: 5509571. DOI: 10.1186/s13065-017-0293-1. View

19.

Ding M, Flaig R, Jiang H, Yaghi O . Carbon capture and conversion using metal-organic frameworks and MOF-based materials. Chem Soc Rev. 2019; 48(10):2783-2828. DOI: 10.1039/c8cs00829a. View

20.

Mahmudov K, Pombeiro A . Control of Selectivity in Homogeneous Catalysis through Noncovalent Interactions. Chemistry. 2023; 29(26):e202203861. DOI: 10.1002/chem.202203861. View