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
Diserahkan: 15
September 2017/Diterima 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 (Ka)
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 (Ka) 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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*Pengarang untuk
surat-menyurat; email: aishah80@ukm.edu.my
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