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 KADIR^1,2*, 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

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