Anion Titration Studies of Tetramide Compounds as A Potential Chromate Separation Materials
DOI:
https://doi.org/10.11113/jomalisc.v2.38Keywords:
Amide, anion, chromate, anion titration, anion bindingAbstract
This study describes the synthesis and characterization of two tetraamide compounds namely, 1,2-bis[N,N’-6-(4-pyridylmethylamido)pyridyl-2-carboxyamido]ethane (L1) and 1,2-bis[N,N’-6-(4-pyridylmethylamido)pyridyl-2-carboxyamido]propane (L2) which were prepared by reacting N-6-[(4-pyridylmethylamino)carbonyl]-pyridine-2-carboxylic acid methyl ester with ethane-1,2-diamine and propane-1,3-diamine, respectively. These types of compounds are commonly studied for anion separation materials due to their pre-organized structure that is readily intended to capture anion via hydrogen bonding. Characterization of L1 and L2 was conducted by Fourier Transform Infrared spectroscopy (FTIR), 1H and 13C Nuclear Magnetic Resonance (NMR). The structure conformation was supported by theoretical studies which were conducted through DFT analysis. Evaluation of the potential of these compounds to interact with chromate anions was investigated using the UV-Vis titration technique. The results showed that L1 has a good affinity towards chromate anions compared to L2. This result concluded that the utilization of smaller spacer units such as ethyl contributed to the ease of binding of a molecular host to chromate anions through NH amide binding pockets, compared to the use of a lengthier spacer.
References
Phuong, T., Cong, T. D., Ta, V. T., Nguyen, T. H. 2022. Study on Leaching of Phosphate from Municipal Wastewater Treatment Plant’s Sewage Sludge and Followed by Adsorption on Mg-Al Layered Double Hydroxide. Journal of Nanomaterials. 2022: 1-9.
Cheng, X., Huang, X., Wang, X., Zhao, B., Chen, A., Sun, D. Sun. 2009. Phosphate Adsorption from Sewage Sludge Filtrate using Zinc-Aluminum Layered Double Hydroxides. Journal of Hazardous Materials. 169: 958–964.
Beniah, O. I., Christian, E. E., 2020. Pollution and Health Risks Assessment of Nitrate and Phosphate Concentrations in Water Bodies in South Eastern. Nigeria, Environmental Advances. 2020:1-8.
Bian, Z., Wang, Y., Zhang, X., Li, T., Grundy, S., Yang, Q., Cheng, R. 2020. A Review of Environment Effects on Nitrate Accumulation in Leafy Vegetables Grown in Controlled Environments, Foods, 9:732-740.
Bai, Y., Long, C., Hu, G., Zhou, D., Gao, X., Chen, Z., Wang, T., Yu, S., Han, Y., Yan, L. 2017. Association of Blood Chromium and Rare Earth Elements with The Risk of DNA Damage in Chromate Exposed Population. Environmental Toxicology & Pharmacology. 72: 103237.
Russ, T. H., Pramanik, A., Khansari, M. E., Wong, B. M., Hossain, M. A. 2012. A Quinoline Based bis-Urea Receptor for Anions: A Selective Receptor for Hydrogen Sulfate. Natural Product Communications, 7:301 – 304.
Navakhun, K.,Techawan, V. 2019. Halide Recognitions of p-substituted Isophthalmide-Based Anion Receptors: Experimental and Theoretical Studies. Ramkhamhaeng International Journal of Science and Technology, 3:23-29.
Martínez-Aguirre, M. A., Otero, D. M., Álvarez-Hernández, M. L., Torres-Blancas. T., Dorazco-González, Yatsimirsky, A. K. 2017. Anion and Sugar Recognition by 2,6-Pyridinedicarboxamide Bis-Boronic Acid Derivatives. Heterocyclic Communications. 23: 171-180.
Haris, N. S. H., Mansor, N., Yusof, M. S. M., Sumby, C. J., Kadir, M. A. 2021. Investigating The Potential of Flexible and Pre-Organized Tetraamide Compounds to Encapsulate Anions in One-Dimensional Coordination Polymers: Synthesis, Spectroscopic Studies and Crystal Structures. Crystals. 11: 77-91.
Sumby, C. J., Hanton, L. R. 2009. Syntheses and Studies of Flexible Amide Ligands: A Toolkit for Studying Metallo-Supramolecular Assemblies for Anion Binding. Tetrahedron. 65: 4681-4691.
Jakob, U, Petersen, T. O., Bannwarth, W. 2015. Unusual Metal complexes of N,N-bis(2-picolyl)amides - A Comparative Study of Structure and Reactivity. Journal Organometallic Chemistry. 797: 46-51.
Thordarson, P. 2011. Determining Association Constants from Titration Experiments Supramolecular Chemistry. Chemical Society Review. 40: 1305-1323.
Chen, L., Berry, S. N., Wu, X., Howe, E. N. W., Gale, P. A. 2020. Advances in Anion Receptor Chemistry. Chem. 6:61-141.
Lopez-Martinez, L.M., Garcia-Elias, J., Ochoa-Teran, A., Ortega, H.S., Ochoa-Lara, K., Montano-Medina, C.U., Yatsimirsky, A. K., Ramirez, J. Z., Labastida-Galvan, V., Ordonez, M. 2017. Synthesis, Characterization And Anion Recognition Studies Of New Fluorescent Alkyl bis(naphthylureylbenzamide)-based Receptors. Tetrahedron. 76:130815.
Roman, P., Julian, K., Kai, T., Louis F. B., Marvin, K., Andrea, M., Julia K., Suresh, K. V., Philip, A. C., Christian, S., Michael, T. W., Rasmus, L., Rochus, S., Sebastian, H. 2021. Frustrated Flexibility in Metal-organic Frameworks. Nature Communications .12:4097-4112.