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Chemiluminescence Demonstration Illustrating Principles of Ester Hydrolysis Reactions
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Abstract
Peroxyoxalate chemiluminescence, the most efficient nonenzymatic chemiluminescence reaction known, is used to demonstrate mechanistic features of analogous ester hydrolysis reactions. The effect of the leaving group pKa and a comparison between nucleophilic and general-base catalysis are demonstrated visually by the kinetics of the light-generating reaction. The demonstration is targeted for undergraduate organic chemistry students but is easily modified for a range of audiences.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
DemonstrationsKeywords (Feature):
Tested DemonstrationsKeywords (Subject):
KineticsCiting Articles
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
A Greener Chemiluminescence Demonstration
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Osman Jilani, Trisha M. Donahue, and Miguel O. MitchellJournal of Chemical Education2011 88 (6), 786-787Because they are dramatic and intriguing, chemiluminescence demonstrations have been used for decades to stimulate interest in chemistry. One of the most intense chemiluminescent reactions is the oxidation of diaryl oxalate diesters with hydrogen peroxide ...
Polyoxalate Nanoparticles as a Biodegradable and Biocompatible Drug Delivery Vehicle
Seho Kim, Kyeongyeol Seong, Onyou Kim, Soojin Kim, Hansol Seo, Myunghoon Lee, Gilson Khang and Dongwon LeeBiomacromolecules2010 11 (3), 555-560Polyoxalate Nanoparticles as a Biodegradable and Biocompatible Drug Delivery Vehicle
Seho Kim, Kyeongyeol Seong, Onyou Kim, Soojin Kim, Hansol Seo, Myunghoon Lee, Gilson Khang and Dongwon LeeBiomacromolecules2010 11 (3), 555-560One of major challenges in the drug delivery lies in the development of nanoparticles that are effectively delivered to targeted cells and release their payload over an extended period to achieve a clinical response. In this paper, we report a new family ...
The Comparative Nucleophilicity of Naphthoxide Derivatives in Reactions with a Fast-Red TR Dye. A Discovery-Oriented Capstone Project for the Second-Year Organic Laboratory
Cheryl M. MascarenhasJournal of Chemical Education2008 85 (9), 1271The Comparative Nucleophilicity of Naphthoxide Derivatives in Reactions with a Fast-Red TR Dye. A Discovery-Oriented Capstone Project for the Second-Year Organic Laboratory
Cheryl M. MascarenhasJournal of Chemical Education2008 85 (9), 1271In this experiment, organic chemistry students perform reactions between three naphthyl acetate derivatives and the diazonium salt Fast-Red TR, under basic conditions. The three naphthyl acetate derivatives used in this study are 2-naphthyl acetate (1a), ...
Synthesis of Chemiluminescent Esters: A Combinatorial Synthesis Experiment for Organic Chemistry Students
Robert Duarte , Janne T. Nielsen and Veljko DragojlovicJournal of Chemical Education2004 81 (7), 1010Synthesis of Chemiluminescent Esters: A Combinatorial Synthesis Experiment for Organic Chemistry Students
Robert Duarte , Janne T. Nielsen and Veljko DragojlovicJournal of Chemical Education2004 81 (7), 1010In this laboratory exercise, a peroxyoxalate chemiluminescence experiment has been integrated with a combinatorial synthesis experiment. Students prepare a number of esters, in reactions between acyl chlorides and phenols, and test the compounds for ...
Automated Flow-Injection Instrument for Chemiluminescence Detection Using a Low-Cost Photodiode Detector: An Interdisciplinary Project in Chemical Instrumentation, Graphical Programming, Computer Interfacing, and Analytical Chemistry
A. Economou , D. Papargyris and J. StratisJournal of Chemical Education2004 81 (3), 406Automated Flow-Injection Instrument for Chemiluminescence Detection Using a Low-Cost Photodiode Detector: An Interdisciplinary Project in Chemical Instrumentation, Graphical Programming, Computer Interfacing, and Analytical Chemistry
A. Economou , D. Papargyris and J. StratisJournal of Chemical Education2004 81 (3), 406This work is concerned with the design, construction, automatic control, and optimization of a flow injection analysis (FIA) instrument with chemiluminescence (CL) detection. The project proceeds in three stages: the construction of the detector, the ...
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- Received: August 03, 2009
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