Substituent and Solvent Effects: Examining Acidity via Infrared Spectroscopy by Jordan Buhle

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Title

Substituent and Solvent Effects: Examining Acidity via Infrared Spectroscopy by Jordan Buhle

Subject

Chemistry

Description

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.

Creator

Buhle, Jordan

Source

Senior Showcase Oral presentation

Publisher

Ripon College

Date

April 23, 2015

Rights

The author reserves all rights.

Format

pdf

Identifier

Major: Chemistry
Minors: Spanish, Physics
Milton, Wisconsin
CHM 502 Chemistry Senior Seminar

Files

Buhle_Thesis.pdf

Citation

Buhle, Jordan, “Substituent and Solvent Effects: Examining Acidity via Infrared Spectroscopy by Jordan Buhle,” Senior Showcase Digital Collection, accessed February 3, 2023, https://rcseniorshowcase.omeka.net/items/show/15.

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