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 . 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 . 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

 

 

RUJUKAN

Adhikari, S., Ghosh, A., Guria, S. & Sahana, A. 2016. A through bond energy transfer based ratiometric probe for fluorescent imaging of Sn2+ ions in living cells. Royal Society of Chemistry Advances 6(46): 39657-39662.

Azizian, J., Mohammadi, M.K., Firuzi, O., Razzaghi-Asl, N. & Miri, R. 2012. Synthesis, biological activity and docking study of some new isatin Schiff base derivatives. Medicinal Chemistry Research 21(11): 3730-3740.

Bamfield, P. 2010. Chromic Phenomena: Technological Applications of Colour Chemistry. Royal Society of Chemistry.

Bao, X., Cao, X., Nie, X., Jin, Y. & Zhou, B. 2014. RBAP, arhodamine B-based derivative: Synthesis, crystal structure analysis, molecular simulation, and its application as a selective fluorescent chemical sensor for Sn2+. Molecules 19(6): 7817-7831.

Beck, J.J. & Chou, S.C. 2007. The structural diversity of phthalides from the Apiaceae. Journal of Natural Products 70(5): 891-900.

Chatterjee, N., Mahaling, B., Sivakumar, S. & Bharadwaj, P.K. 2016. A highly selective and ensitive “turn-on” fluorescence chemosensor for the Cu2+ ion in aqueous ethanolic medium and its application in live cell imaging. Journal of Photochemistry and Photobiology A: Chemistry 330: 110-116.

Chunaev, Y.M., Przhiyalgovskaya, N.M., Kurkovskaya, L.N. & Gal’bershtam, M.A. 1982. Reaction of the Fischer base with 8-hydroxy-1-naphthaldehydes: Investigation of the reaction products by 13C NMR spectroscopy. Chemistry of Heterocyclic Compounds 18(11): 1164-1169.

Gangrade, D., Lad, S. & Mehta, A. 2015. Overview on microwave synthesis-Important tool for green Chemistry. International Journal of Research in Pharmacy & Science 5(2): 37-42.

Howe, P. & Watts, P. 2005. Tin and Inorganic Tin Compounds. World Health Organization.

Jadhav, A.G., Shinde, S.S., Lanke, S.K. & Sekar, N. 2017. Benzophenone based fluorophore for selective detection of Sn2+ ion: Experimental and theoretical study. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 174: 291-296.

Karmakar, R., Pahari, P. & Mal, D. 2014. Phthalides and phthalans: Synthetic methodologies and their applications in the total synthesis. Chemical Reviews 114(12): 6213-6284.

Keum, S.R., Lee, M.H., Ma, S.Y., Kim, D.K. &  Roh, S.J. 2011. Novel unsymmetrical leuco-TAM,(2E,2′E)- 2,2′-{(E)-4-phenylpent-2-ene-1,5-diylidene}bis(1,3,3- trimethylindoline) derivatives: Synthesis and structure elucidation. Dyes and Pigments 90(3): 233-238.

Landge, S.M., Berryman, M. & Toeroek, B. 2008. Microwave- assisted solid acid-catalyzed one-pot synthesis of isobenzofuran-1(3H)-ones. Tetrahedron Letters 49(29): 4505-4508.

Li, P. & Xiao, S. 2016. A highly sensitive and selective sensor based on imidazo[1,2-a]pyridine for A13+. Journal of Photochemistry and Photobiology A: Chemistry 330(Supplement C): 169-174.

Mathews, T.J., Looney, B.B., Bryan, A.L., Smith, J.G., Miller, C.L., Southworth, G.R. & Peterson, M.J. 2015. The effects of a stannous chloride-based water treatment system in a mercury contaminated stream. Chemosphere 138: 190-196.

Michael Barbour, P., Podoll, J.D., Marholz, L.J. & Wang, X. 2014. Discovery and initial structure-activity relationships of N-benzyl tricyclic indolines as antibacterials for methicillin- resistant Staphylococcus aureus. Bioorganic & Medicinal Chemistry Letters 24(24): 5602-5605.

Peeters, K., Zuliani, T., Ščančar, J. & Milačič, R. 2014. The use of isotopically enriched tin tracers to follow the transformation of organotin compounds in landfill leachate. Water Research 53(Supplement C): 297-309.

Qu, S., Zheng, C., Liao, G., Fan, C., Liu, G. & Pu, S. 2017. A fluorescent chemosensor for  Sn2+ and  Cu2+ based  on a carbazole-containing diarylethene. Royal Society of Chemistry Advances 7(16): 9833-9839.

Srivastava, K., Singh, S. & Kumar, H. 2013. Microwave assisted synthesis and photochemical reactions of 3-(amine dithiocarbamyl) phthalides. Pharmaceutical Chemistry 5(1): 137-144.

Sun, W., Guo, S., Hu, C., Fan, J. & Peng, X. 2016. Recent development of chemosensors based on cyanine platforms. Chemical Reviews 116(14): 7768-7817.

Wang, J., Lv, M., Wang, Z., Zhou, M., Gu, C. & Guo, C. 2015. Highly sensitive and selective  fluorescent detection of rare earth metal Sn(II) ion by organic fluorine Schiff base functionalized periodic mesoporous material in aqueous solution. Journal of Photochemistry and Photobiology A: Chemistry 309(Supplement C): 37-46.

Zhu, H., Fan, J., Wang, B. & Peng, X. 2015. Fluorescent, MRI, and colorimetric chemical sensors for the first-row d-block metal ions. Chemical Society Reviews 44(13): 4337-4366.

 

*Pengarang untuk surat-menyurat; email: aishah80@ukm.edu.my

 

 

 

 

 

 

 

 

 

 

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