Sains Malaysiana 48(7)(2019): 1473–1481

http://dx.doi.org/10.17576/jsm-2019-4807-16

 

Synthesis, Structural Elucidation and Anion Binding Studies of Isophthalamide Derivatives as Potential Receptor for Chromate Anions

(Kajian Sintesis, Penentuan Struktur dan Pengikatan Anion Terbitan Isoptalamida Berpotensi sebagai Reseptor untuk Anion Kromat)

 

MAISARA ABDUL KADIR1,2*, SYAHIRAH OMAR1, NUR SHUHAILA HARYANI ABD HARIS1 & RAMIZAH RAMLI1

 

1Faculty of Science and Marine Environment, , Universiti Malaysia Terengganu, 21030 Kuala Nerus, Terengganu Darul Iman, Malaysia

 

2Advanced Nano Materials (ANoMa) Research Groups, Faculty of Science and Marine Environment, , Universiti Malaysia Terengganu, 21030 Kuala Nerus, Terengganu Darul Iman, Malaysia

 

Received: 15 December 2018/Accepted: 28 March 2019

 

ABSTRACT

This study highlights the synthesis and structural elucidation of two new isophthalamide isomers namely N,N'-1,3-bis(4-methylpyridin-2-yl)isophthalamide (4-MPI) and N,N'-1,3-bis(5-methylpyridin-2-yl)isophthalamide (5-MPI), prepared from reaction between isophthaloyl chloride with 2-amino-4-methylpyridine and 2-amino-5-methylpyridine, respectively. Their potential studies as anion receptors for chromate anions are also include in this paper. Characterization of these compounds were accomplished using common spectroscopic techniques such as Fourier Transform Infrared (FT-IR), 1H and 13C Nuclear Magnetic Resonance (NMR), UV-Vis spectrometer and mass spectrometry. FTIR analysis showed the presence of four significant peaks comprising ν(N-H), ν(C-H), ν(C=O) and δ(N-H) at range 3256-3274 cm-1, 2812-2928 cm-1, 1662-1686 cm-1 and 1533-1537 cm-1, respectively. Meanwhile, 1H NMR confirmed the presence of methyl, aromatic carbon and amide resonances at δH 2.983-2.994 ppm, 6.860-8.974 and 10.138-11.300 ppm, respectively. In the 13C NMR spectra, the appearance of methyl, aromatic and carbonyl carbon signals were determined at δC 18.45-20.59 ppm, 108.42-159.22 ppm and 167.04-167.20 ppm, respectively. UV-Vis study showed that 4-MPI and 5-MPI shows promising potential as anion receptors for chromate anions.

 

Keywords: Anion; chromate; isophthalamide; receptor

 

ABSTRAK

Kajian ini menekankan sintesis dan penentuan struktur dua sebatian isomer baharu terbitan isoptalamida, iaitu N,N'-1,3-bis(4-metilpiridina-2-il)isoptalamida (4-MPI) dan N,N'-1,3-bis(5-metilpiridina-2-il)isoptalamida (5-MPI) yang disediakan melalui tindak balas antara isoptaloil klorida masing-masing dengan 2-amino-4-metilpiridina and 2-amino-5-metilpiridina. Pencirian terhadap sebatian ini dilakukan melalui gabungan beberapa teknik spektroskopi seperti Transformasi Fourier inframerah (FT-IR), 1H dan 13C Resonans Magnetik Nukleus (NMR), UV-Vis dan spektrometer jisim. Spektrum FTIR menunjukkan kehadiran lima puncak penting mengandungi ν(N-H), ν(C-H), ν(C=O) dan δ(N-H) masing-masing pada julat 3256-3274 cm-1, 2812-2928 cm-1, 1662-1686 cm-1 dan 1533-1537 cm-1. Keputusan data 1H RMN mengesahkan kehadiran resonans metil, aromatik dan amida masing-masing pada julat δH 2.983-2.994 ppm, 6.860-8.974 dan 10.138-11.300 ppm. Manakala, spektra 13C RMN menunjukkan kehadiran signal metil, aromatik dan karbonil masing-masing pada δC 18.45-20.59 ppm, 108.42-159.22 ppm dan 167.04-167.20 ppm. Analisis UV-Vis menunjukkan bahawa sebatian 4-MPI dan 5-MPI mempunyai potensi sebagai reseptor untuk anion kromat.

 

Kata kunci: Anion; isoptalamida; kromat; reseptor

REFERENCES

Adam, F., Fatihah, N.N., Ameram, N., Subramaniam, S. & Mubarrakh, S.A. 2016. The synthesis and characterisation of 2-methyl-N-((4-methylpyridine-2-yl) carbamothiol) benzamide: Its preparation with antibacterial study. Journal of Physical Science 27(2): 83-101.

Ameram, N. & Yamin, B.M. 2013. Synthesis and characterization o-, m-and para-toluyl thiourea substituted para-pyridine and ethyl pyridine as a chromoionophore. IOSR Journal of Applied Chemistry 4(6): 59-67.

Barakat, A., Al-Najjar, H.J., Al-Majid, A.M., Soliman, S.M., Mabkhot, Y.N., Ghabbour, H.A. & Fun, H.K. 2015. Synthesis and molecular characterization of 5,5′-((2,4-dichlorophenyl) methylene)bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)- trione). Journal of Molecular Structure 1084: 207-215.

Bezerra, B.G.P., Parodia, A., da Silva, D.R. & Pergher, S.B.C. 2019. Cleaning produced water: A study of cation and anion removal using different adsorbents. Journal of Environmental Chemical Engineering 7(2): 103006.

Cametti, M. & Rissanen K. 2013. Highlights on contemporary recognition and sensing of fluoride anion in solution and in the solid state. Chemical Society Review. 42: 2016-2038.

Cametti, M. & Rissanen, K. 2009. Recognition and sensing of fluoride. Chemical Communication 20: 2809-2829.

Dong, Z.Y., Yang, Y., Zhang, L.F., Xue, Y.R., Feng, M.Y. & Gao, G.H. 2012. Ionic liquids containing the urea moiety for recognition of halides and complex anions. Chinese Science Bulletin 57: 473-478.

Gale, P.A. 2000. Anion coordination and anion-directed assembly: Highlights from 1997 and 1998. Coordination Chemistry Reviews 199: 181-233.

Gao, Q., Xu, J. & Bu, X.H. 2018. Recent advances about metal-organic frameworks in the removal of pollutants from wastewater. Coordination Chemistry Reviews 378: 17-31.

Hassan, I.N., Rahim, F., Hanifah, S.A., Tarawneh, M.A. & Yamin, B.M. 2015. Synthesis, characterization, spectroscopic and X-ray diffraction studies of novel pair of thiourea derivatives of 2-morpholine-4-yl-ethylamine. Asian Journal of Chemistry 27(10): 3711-3715.

Hsu, L.C., Tzou, Y.M., Chiang, P.N., Fu, W.M., Wang, M.K., Teah, H.Y. & Liu, Y.T. 2019. Adsorption mechanisms of chromate and phosphate on hydrotalcite: A combination of macroscopic and spectroscopic studies. Environmental Pollution 247: 180-187.

Kadir, M.A. & Sumby, C.J. 2018. Synthesis, characterization and crystal structure of coordination polymers developed as anion receptor. Solid State Phenomena 273: 134-139.

Kadir, M.A., Mansor, N. & Osman, U.M. 2017. Synthesis and structural characterization of 6-(N-methyl-pyridin- 2-ylcarbamoyl)-pyridine-2-carboxylic acid methyl ester isomers. Sains Malaysiana 46(5): 725-731.

Kai, C.C., Shih, S.S., Maurice, O.O. & Alistair, J.L. 2015. Anion recognition and sensing by transition-metal complexes with polarized N-H recognition motifs. Coordination Chemistry Reviews 284: 111-123.

Katritzky, A.R., Maran, U., Karelson, M. & Lobanov, V.S. 1997. Prediction of melting points for the substituted benzenes: A QSPR approach. Journal of Chemical Information and Computer Sciences 37(5): 913-919.

Kurt, G. & Mercimek, B. 2009. Preparation of new benzoylthiourea-functionalized PVC resin and investigation on the complexation properties. Journal of Inorganic and Organometallic Polymers and Materials 19: 367-373.

Lin, H., Cui, Z., Tian, Y., Wang, X. & Liu, G. 2018. Assembly, fluorescent and adsorption properties of two cadmium(ii)/ cobalt(ii) coordination complexes functionalized by the flexible bis(pyridyl)-bis(amide) ligand. Journal of Inorganic and Organometallic Polymers and Materials 28: 1810.

Movassaghi, M. & Hill, M.D. 2006. Single-step synthesis of pyrimidine derivatives. Journal of the American Chemical Society 128(44): 14254-14255.

Pavia, D.L., Lampman, G.M., Kriz, G.S. & Vyvyan, J.R. 2015. Introduction to Spectroscopy. 5th ed. Washington: Cengage Learning Asia.

Rabiatun, H.J., Wan, M.K., Mohd, S.M.Y., Maisara, A.K. & Bohari, M.Y. 2011. Structural and spectroscopic studies of novel methylbenzoyl thiourea derivatives. Malaysian Journal of Analytical Sciences 15(1): 70-80.

Ranjan, D. & Pradyut, G. 2014. Recent developments in anion induced capsular self-assemblies. Chemical Communication 50: 10538-10554.

Rao, S.P. & Sunkada, S. 2007. Making sense of boiling points and melting points. Resonance 12(6): 43-57.

Schmuck, C. & Machon, U. 2005. Amino acid binding by 2‐(guanidiniocarbonyl) pyridines in aqueous solvents: A comparative binding study correlating complex stability with stereoelectronic factors. Chemistry-A European Journal 11(4): 1109-1118.

Shi et al. (2012) and Shao et al. (2009) – author, kindly assist to provie full details. Thank you.

Shoaib, M., Shafiullah, Ul-Bari, A., Tahir, M.N. & Shah, S.W.A. 2014. Acute toxicity, brine shrimp cytotoxic, antioxidant and analgesic activities of synthesized 1-benzoyl-3-methyl thiourea. Pharmacology Online 3: 91-99.

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(24): 4681-4691.

Sunkari, J., Kundha, S., Gundapaneni, R.R., Reddy, A., Pola, S., Kodumuru, S. & Sreedasyam, J.S. 2015. Supramolecular interactions between a diamine-diamide ligand and anions, trigonal planar NO3- and spherical Cl-: Multiple hydrogen bond cooperativity through water molecules. Indian Journal of Chemistry 54(A): 596-606.

Yalçin, Ş.P., Ceylan, Ü., Sarioğlu, A.O., Sönmez, M. & Aygün, M. 2015. Synthesis, structural, spectral (FT-IR, 1H and 13C NMR and UV-Vis), NBO and first order hyperpolarizability analysis of N-(4-nitrophenyl)-2,2-dibenzoylacetamide by density functional theory. Journal of Molecular Structure 1098: 400-407.

Yusof, M.S.M., Jusoh, R.H., Khairul, W.M. & Yamin, B.M. 2010. Synthesis and characterisation of N-(3,4- dichlorophenyl)-N’-(2,3 and 4-methylbenzoyl)thiourea derivatives. Journal of Molecular Structure 975: 280-284.

Zhao, M.M., Dong, X.Y., Li, G., Yang, Y.H., Zhang, Y.J. & Yang, X.Q. 2013. Antituberculosis and antifungal activities of synthesized benzoylthiourea derivatives. Asian Journal of Chemistry 25(13): 7548-7550.

Zhao, J., Yang, D., Yang, X.J. & Wu, B. 2018. Anion coordination chemistry: From recognition to supramolecular assembly. Coordination Chemistry Reviews 378: 415-444.

 

*Corresponding author; email: maisara@umt.edu.my

 

 

 

previous