X-ray crystal structure and cation binding properties of a new phthalide-fused indoline derivative

Research output: Contribution to journalArticle

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 Pi. 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.

Original languageEnglish
Pages (from-to)755-762
Number of pages8
JournalSains Malaysiana
Volume47
Issue number4
DOIs
Publication statusPublished - 1 Apr 2018

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Cations
Crystal structure
Metals
Derivatives
X rays
Crystallography
Microwave irradiation
Titration
Molecular structure
Carbon
Acids
indoline
phthalide

Keywords

  • Binding study
  • Chemical sensor
  • Green synthesis
  • Phthalide-indoline
  • Sn(II) ion

ASJC Scopus subject areas

  • General

Cite this

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title = "X-ray crystal structure and cation binding properties of a new phthalide-fused indoline derivative",
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 Pi. 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",
author = "Wong Sheryn and Jalifah Latip and Hassan, {Nurul Izzaty} and Hasbullah, {Siti Aishah}",
year = "2018",
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T1 - X-ray crystal structure and cation binding properties of a new phthalide-fused indoline derivative

AU - Sheryn, Wong

AU - Latip, Jalifah

AU - Hassan, Nurul Izzaty

AU - Hasbullah, Siti Aishah

PY - 2018/4/1

Y1 - 2018/4/1

N2 - 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 Pi. 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.

AB - 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 Pi. 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.

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