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https://d1y502jg6fpugt.cloudfront.net/17269/archive/files/b91d24b41bf831993e56141bf2a6f045.pdf?Expires=1712793600&Signature=BcEhnReqBVZV4ExY514B8R1cnlOdT1NW7uGrfB%7EXsr2Qws7lQKJLIxkU8mW-axtnCIUudOX1DdJ9ZEYKilKpz3bAIl1rvC%7EOukhvdDhTYAn84PjPAJIyPXi%7EeaIQc5kMrsnuCDCEwjT099cbRrP2U9VDe%7Eqte0QqzeIIic1akt4jY5KhfbXDtTzjp54-d7cOQ1H1hNAwAXOTg4jMgIKi2MgwttOL1xFWj6GCnxQg0iEqIRMS01kaiV9zPjnAJZmp6MlUhYvVciq-p-WHZUk82oxo85A4xYN4qB4miQecGB6TryTzAylDM6L6mQ8D9KPJD8bQsuQixecYcx9KiGpW-Q__&Key-Pair-Id=K6UGZS9ZTDSZM
d9614ac2cbeae3a14ed1689ddc4f44c3
Dublin Core
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Senior Showcase 2015
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Oral and poster presentations from Senior Showcase held on April 23, 2015 at Ripon College.
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Ripon College
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Ripon College Lane Library
Date
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April 23, 2015
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Scholars Week
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pdf
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The Dublin Core metadata element set is common to all Omeka records, including items, files, and collections. For more information see, http://dublincore.org/documents/dces/.
Title
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Substituent and Solvent Effects: Examining Acidity via Infrared Spectroscopy by Jordan Buhle
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Chemistry
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Buhle, Jordan
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Senior Showcase Oral presentation
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Ripon College
Date
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April 23, 2015
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pdf
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Major: Chemistry
Minors: Spanish, Physics
Milton, Wisconsin
CHM 502 Chemistry Senior Seminar
Description
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There is a large collection of substituent constant data measured in polar protic and polar aprotic solvents, but a lack of information on substituent effects in nonpolar aprotic solvents. In this study, substituent effects on the acidities of phenol derivatives were examined in CCl4 using infrared (IR) spectroscopy. The IR peak of the free phenolic -OH appears at approximately 3600 cm-1 which is red shifted in the presence of a hydrogen bond acceptor. The magnitude of the splitting between the free and the hydrogen-bonded -OH peak is related to the acidity of the protic hydrogen. Deuterated acetonitrile was used as the hydrogen-bond acceptor to probe the relative acidities of 21 phenol derivatives in CCl4. While most phenol derivatives exhibited similar acidity trends in CCl4 as in DMSO and the gas phase, several demonstrated a reduction in acidity which indicates a solvent dependence on substituent effects. This study offers a facile method to examine substituent effects on the acidity of alcohols and has identified several solvent-dependent substituent effects.
Acidity
Chemistry
IR spectroscopy
Solvent
Substituents