Synthesis and Separation of a Diastereomeric Sulfonium Ion by Capillary Zone Electrophoresis

Francisco A. Valenzuela , Thomas K. Green and Darwin B. Dahl
Department of Chemistry, Western Kentucky University, Bowling Green, KY 42101
J. Chem. Educ., 1998, 75 (12), p 1590
DOI: 10.1021/ed075p1590
Publication Date (Web): December 1, 1998

Abstract

An undergraduate laboratory exercise utilizing capillary zone electrophoresis in the analysis of the student-synthesized sulfonium ion sec-butylmethyl-p-tolylsulfonium tetrafluoroborate is presented. The sulfonium ion contains two stereogenic centers and thereby yields four optical isomers. Sulfated cyclodextrin is used as the buffer modifier to achieve chiral separation. Additionally, the NMR spectrum for this compound is presented and discussed.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Analytical Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Electrophoresis

Citing Articles

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This article has been cited by 7 ACS Journal articles (5 most recent appear below).

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    Capillary Electrophoresis: Focus on Undergraduate Laboratory Experiments

    Lisa A. Holland
    Journal of Chemical Education2011 88 (3), 254-256
    • Capillary Electrophoresis: Focus on Undergraduate Laboratory Experiments

      Lisa A. Holland
      Journal of Chemical Education2011 88 (3), 254-256

      Capillary electrophoresis is a versatile technique well suited to teach concepts that are fundamental to a chemistry degree program. The applicability of capillary electrophoresis to metabolites, DNA, proteins, pharmaceutical compounds, environmental ...

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    Weak Acid pKa Determination Using Capillary Zone Electrophoresis

    Mike Solow
    Journal of Chemical Education2006 83 (8), 1194
    • Weak Acid pKa Determination Using Capillary Zone Electrophoresis

      Mike Solow
      Journal of Chemical Education2006 83 (8), 1194

      This article describes a general chemistry experiment designed to measure the pKa of benzoic acid using capillary zone electrophoresis. Despite the fact that modern biology relies so heavily on this analytical technique, students get very little ...

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    Capillary Electrophoresis Analysis of Substituted Benzoic Acids. An Experiment for the Organic Synthesis Laboratory

    Nancy S. Mills , John D. Spence and Michelle M. Bushey
    Journal of Chemical Education2005 82 (8), 1226
    • Capillary Electrophoresis Analysis of Substituted Benzoic Acids. An Experiment for the Organic Synthesis Laboratory

      Nancy S. Mills , John D. Spence and Michelle M. Bushey
      Journal of Chemical Education2005 82 (8), 1226

      Capillary electrophoresis is gradually working its way into the undergraduate laboratory curriculum. Typically, experiments utilizing this technology have been introduced into analytical or instrumental courses. We have introduced an experiment into the ...

  • Cover Image

    Capillary Electrophoresis Analysis of Cations in Water Samples. An Experiment for the Introductory Laboratory

    Christopher J. Pursell , Bert Chandler and Michelle M. Bushey
    Journal of Chemical Education2004 81 (12), 1783
    • Capillary Electrophoresis Analysis of Cations in Water Samples. An Experiment for the Introductory Laboratory

      Christopher J. Pursell , Bert Chandler and Michelle M. Bushey
      Journal of Chemical Education2004 81 (12), 1783

      Capillary electrophoresis is gradually working its way into the undergraduate laboratory curriculum. Typically, experiments utilizing this newer technology have been introduced into analytical or instrumental courses. We have introduced an experiment into ...

  • Cover Image

    Determination of a Diffusion Coefficient by Capillary Electrophoresis. An Experiment for the Physical and Biophysical Chemistry Laboratories

    Kathryn R. Williams , Bhavin Adhyaru , Igor German and Thomas Russell
    Journal of Chemical Education2002 79 (12), 1475
    • Determination of a Diffusion Coefficient by Capillary Electrophoresis. An Experiment for the Physical and Biophysical Chemistry Laboratories

      Kathryn R. Williams , Bhavin Adhyaru , Igor German and Thomas Russell
      Journal of Chemical Education2002 79 (12), 1475

      Students measure the diffusion coefficient of dopamine (3-hydroxytyramine) by capillary electrophoresis using three evaluation methods: single-point, graphical, and stopped migration. The experiment combines instruction of modern instrumentation with the ...

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  • Received: August 03, 2009

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