Synthesis and characterization of sterically congested mesityltris(imidazolium) salts and the corresponding highly crystalline tris-selone derivatives

Ipsita Nath, Jeet Chakraborty, Francis Verpoort

Research output: Contribution to journalArticle

Abstract

The tandem synthesis of 1,1′,1″-[mesityltris(methylene)tris(3-R-1H-imidazolium)] bromides (3a–f; R=methyl, isopropyl, vinyl, allyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl) and corresponding tris-selones 4a–f starting from tris(bromomethyl)mesitylene was investigated. The compounds were characterized by 1H, 13C, DEPT-135, HSQC, and HMBC NMR spectroscopy; IR spectroscopy; and elemental analysis. The unprecedented crystalline structures of the sterically hindered and synthetically challenging tris-selones possessing different geometrical orientations (with the exception of 4 f) were further corroborated by single-crystal X-ray diffraction analysis. Comparative UV/Vis analysis of 4a–f was also demonstrated.

Original languageEnglish
JournalChemistryOpen
Volume6
Issue number5
DOIs
Publication statusPublished - 1 Jan 2017

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Bromides
X ray diffraction analysis
Nuclear magnetic resonance spectroscopy
Infrared spectroscopy
Salts
Single crystals
Crystalline materials
Derivatives
Chemical analysis
mesitylene

Keywords

  • Crystallinity
  • NMR spectroscopy
  • Selenium
  • Structure elucidation
  • X-ray diffraction

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Synthesis and characterization of sterically congested mesityltris(imidazolium) salts and the corresponding highly crystalline tris-selone derivatives",
abstract = "The tandem synthesis of 1,1′,1″-[mesityltris(methylene)tris(3-R-1H-imidazolium)] bromides (3a–f; R=methyl, isopropyl, vinyl, allyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl) and corresponding tris-selones 4a–f starting from tris(bromomethyl)mesitylene was investigated. The compounds were characterized by 1H, 13C, DEPT-135, HSQC, and HMBC NMR spectroscopy; IR spectroscopy; and elemental analysis. The unprecedented crystalline structures of the sterically hindered and synthetically challenging tris-selones possessing different geometrical orientations (with the exception of 4 f) were further corroborated by single-crystal X-ray diffraction analysis. Comparative UV/Vis analysis of 4a–f was also demonstrated.",
keywords = "Crystallinity, NMR spectroscopy, Selenium, Structure elucidation, X-ray diffraction",
author = "Ipsita Nath and Jeet Chakraborty and Francis Verpoort",
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T1 - Synthesis and characterization of sterically congested mesityltris(imidazolium) salts and the corresponding highly crystalline tris-selone derivatives

AU - Nath, Ipsita

AU - Chakraborty, Jeet

AU - Verpoort, Francis

PY - 2017/1/1

Y1 - 2017/1/1

N2 - The tandem synthesis of 1,1′,1″-[mesityltris(methylene)tris(3-R-1H-imidazolium)] bromides (3a–f; R=methyl, isopropyl, vinyl, allyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl) and corresponding tris-selones 4a–f starting from tris(bromomethyl)mesitylene was investigated. The compounds were characterized by 1H, 13C, DEPT-135, HSQC, and HMBC NMR spectroscopy; IR spectroscopy; and elemental analysis. The unprecedented crystalline structures of the sterically hindered and synthetically challenging tris-selones possessing different geometrical orientations (with the exception of 4 f) were further corroborated by single-crystal X-ray diffraction analysis. Comparative UV/Vis analysis of 4a–f was also demonstrated.

AB - The tandem synthesis of 1,1′,1″-[mesityltris(methylene)tris(3-R-1H-imidazolium)] bromides (3a–f; R=methyl, isopropyl, vinyl, allyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl) and corresponding tris-selones 4a–f starting from tris(bromomethyl)mesitylene was investigated. The compounds were characterized by 1H, 13C, DEPT-135, HSQC, and HMBC NMR spectroscopy; IR spectroscopy; and elemental analysis. The unprecedented crystalline structures of the sterically hindered and synthetically challenging tris-selones possessing different geometrical orientations (with the exception of 4 f) were further corroborated by single-crystal X-ray diffraction analysis. Comparative UV/Vis analysis of 4a–f was also demonstrated.

KW - Crystallinity

KW - NMR spectroscopy

KW - Selenium

KW - Structure elucidation

KW - X-ray diffraction

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