Sains Malaysiana 47(4)(2018): 755-762

http://dx.doi.org/10.17576/jsm-2018-4704-14

X-Ray Crystal Structure and Cation Binding Properties of a New Phthalide-fused

Indoline Derivative

(Struktur Hablur Sinar-X dan Sifat Pengikat Kation bagi Terbitan Ftalida-Indolin)

WONG SHERYN, JALIFAH LATIP, NURUL IZZATY HASSAN & SITI AISHAH HASBULLAH*

Pusat Pengajian Sains dan Teknologi Makanan, Fakulti Sains dan Teknologi, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

Received: 15 September 2017/Accepted: 2 November 2017

ABSTRACT

An efficient and a green route to synthesize phthalide-fused indoline, 3-[(5-chloro-1,3,3-trimethylindolin-2-ylidene)methyl] isobenzofuran-1(3H)-one (3) has been developed by the coupling reaction of 5-chloro-2-methylene-1,3,3-trimethylindoline, 1 and 2-formylbenzoic acid, 2 under solvent-free domestic microwave irradiation. The compound was produced in 85% yield. Compound 3 was characterized by analytical and spectral methods and its structure was confirmed by chemical crystallography. Compound 3 was successfully crystallized in triclinic system with space group Pī. The molecular structure consists of fused 1 and 2 groups connected by the enamine carbon. Binding study of 3 towards different types of metal cations was done by colorimetric detection and UV-vis titrations. Compound 3 exhibited good selectivity and sensitivity for Sn²⁺ compared to other metal cations tested. The stoichiometric binding ratio of 3 toward Sn²⁺ is found to be 1:1 and the binding constant (K_a) is 1.07×10⁴ M^-1 on the basis of Job’s plot and Benesi-Hildebrand analysis.

Keywords: Binding study; chemical sensor; green synthesis; Phthalide-indoline; Sn(II) ion

ABSTRAK

Satu kaedah sintesis hijau dan cekap bagi sintesis ftalida-indolin, 3-[(5-kloro-1,3,3-trimetilindolin-2-ylidin)metil] isobenzofuran-1(3H)-on (3), telah dibangunkan melalui tindak balas pengkupelan antara 5-kloro-2-metilin-1,3,3- trimetilindolin, 1 dan asid 2-formilbenzoik, 2 menggunakan iradiasi gelombang mikro tanpa pelarut dengan peratusan 85%. Sebatian 3 telah dicirikan melalui kaedah analisis dan spektrum, serta strukturnya disahkan melalui kristalografi kimia. Hablur tunggal sebatian 3 telah berjaya dihasilkan dan mempunyai sistem hablur triklinik dengan kumpulan ruang Pī. Struktur molekul 3 adalah merupakan gabungan kumpulan 1 dan 2 yang berikat pada karbon enamin. Kajian pengikatan antara sebatian 3 dengan pelbagai kation logam telah dijalankan menggunakan kaedah kolorimetri dan kaedah pentitratan ultralembayung boleh nampak (UV-vis). Sebatian 3 menunjukkan kepilihan dan kepekaan yang baik terhadap ion Sn²⁺ berbanding dengan kation logam lain yang diuji. Nisbah stoikiometri pengikatan antara 3 dengan Sn²⁺ dan pemalar pengikatan (K_a) masing-masing adalah 1:1 dan 1.07×10⁴ M^-1 berdasarkan plot Job dan analisis Benesi-Hildebrand.

Kata kunci: Ftalida-indolin; ion Sn(II); kajian pengikatan; penderia kimia; sintesis hijau

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*Corresponding author; email: aishah80@ukm.edu.my