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Deriving the Turnover Frequency of Aminoxyl-Catalyzed Alcohol Oxidation by Chronoamperometry: An Introduction to Organic Electrocatalysis

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Title: Deriving the Turnover Frequency of Aminoxyl-Catalyzed Alcohol Oxidation by Chronoamperometry: An Introduction to Organic Electrocatalysis
Language: English
Authors: Goes, Shannon L. (ORCID 0000-0001-5702-0799), Mayer, Mikayla N., Nutting, Jordan E. (ORCID 0000-0003-4017-8834), Hoober-Burkhardt, Lena E., Stahl, Shannon S. (ORCID 0000-0002-9000-7665), Rafiee, Mohammad (ORCID 0000-0002-5325-5387)
Source: Journal of Chemical Education. Feb 2021 98(2):600-606.
Availability: Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Peer Reviewed: Y
Page Count: 7
Publication Date: 2021
Sponsoring Agency: National Institutes of Health (DHHS)
National Science Foundation (NSF), Division of Graduate Education (DGE)
Contract Number: R35GM134929
1747503
Document Type: Journal Articles
Reports - Research
Education Level: Higher Education
Postsecondary Education
Descriptors: Science Instruction, College Science, Hands on Science, Teaching Methods, Science Laboratories, Laboratory Experiments, Science Experiments, Chemistry, Scientific Concepts, Concept Formation, Measurement
DOI: 10.1021/acs.jchemed.0c01244
ISSN: 0021-9584
Abstract: Organic electrosynthesis is an increasingly popular tool for driving and probing redox reactions. Recent advances in this field often employ an electrocatalyst to enhance the selectivity and efficiency of electrochemical reactions. A laboratory experiment was developed to introduce students to relevant mechanistic techniques in electrochemistry for analysis of electrocatalytic reactions using aminoxyl-catalyzed alcohol oxidation as a case study. This lab activity employs cyclic voltammetry for qualitative assessment of catalytic turnover prior to introducing students to chronoamperometry, an underutilized technique that facilitates quantitative determination of the rate of catalysis. Students identify and rationalize the important features of a reversible electron transfer and a catalytic reaction in a cyclic voltammogram, probe the origin of scan rate effects on these traces, and calculate turnover frequency using a series of chronoamperograms. The method employs safe and readily available reagents: basic aqueous buffer solution, alcohol substrate, and an inexpensive organic aminoxyl catalyst. Student data presented herein were obtained from a course attended by undergraduate students, graduate students, and pharmaceutical chemists.
Abstractor: As Provided
Entry Date: 2021
Accession Number: EJ1287141
Database: ERIC
FullText Text:
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  Data: Deriving the Turnover Frequency of Aminoxyl-Catalyzed Alcohol Oxidation by Chronoamperometry: An Introduction to Organic Electrocatalysis
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  Data: <searchLink fieldCode="AR" term="%22Goes%2C+Shannon+L%2E%22">Goes, Shannon L.</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0001-5702-0799">0000-0001-5702-0799</externalLink>)<br /><searchLink fieldCode="AR" term="%22Mayer%2C+Mikayla+N%2E%22">Mayer, Mikayla N.</searchLink><br /><searchLink fieldCode="AR" term="%22Nutting%2C+Jordan+E%2E%22">Nutting, Jordan E.</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0003-4017-8834">0000-0003-4017-8834</externalLink>)<br /><searchLink fieldCode="AR" term="%22Hoober-Burkhardt%2C+Lena+E%2E%22">Hoober-Burkhardt, Lena E.</searchLink><br /><searchLink fieldCode="AR" term="%22Stahl%2C+Shannon+S%2E%22">Stahl, Shannon S.</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0002-9000-7665">0000-0002-9000-7665</externalLink>)<br /><searchLink fieldCode="AR" term="%22Rafiee%2C+Mohammad%22">Rafiee, Mohammad</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0002-5325-5387">0000-0002-5325-5387</externalLink>)
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  Data: <searchLink fieldCode="SO" term="%22Journal+of+Chemical+Education%22"><i>Journal of Chemical Education</i></searchLink>. Feb 2021 98(2):600-606.
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  Data: Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
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  Data: Organic electrosynthesis is an increasingly popular tool for driving and probing redox reactions. Recent advances in this field often employ an electrocatalyst to enhance the selectivity and efficiency of electrochemical reactions. A laboratory experiment was developed to introduce students to relevant mechanistic techniques in electrochemistry for analysis of electrocatalytic reactions using aminoxyl-catalyzed alcohol oxidation as a case study. This lab activity employs cyclic voltammetry for qualitative assessment of catalytic turnover prior to introducing students to chronoamperometry, an underutilized technique that facilitates quantitative determination of the rate of catalysis. Students identify and rationalize the important features of a reversible electron transfer and a catalytic reaction in a cyclic voltammogram, probe the origin of scan rate effects on these traces, and calculate turnover frequency using a series of chronoamperograms. The method employs safe and readily available reagents: basic aqueous buffer solution, alcohol substrate, and an inexpensive organic aminoxyl catalyst. Student data presented herein were obtained from a course attended by undergraduate students, graduate students, and pharmaceutical chemists.
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