Document Type


Date of Award


Degree Name

Master of Science in Chemistry - (M.S.)


Chemical Engineering and Chemistry

First Advisor

Arthur Greenberg

Second Advisor

Joel F. Liebman

Third Advisor

Carol A. Venanzi


Thermodynamic stabilization energies are presented for a series of monosubstituted vinyl, cyclopropyl, ethynyl, and phenyl compounds. The energies are calculated using ab initio molecular orbital calculations at the 4-31G level, and also with published experimental heat of formation data. Correlation analyses are then attempted with the dual substituent parameter approach with the stabilization energies. The analyses are also attempted with a triple-parameter approach using Topsom's theoretically calculated X, F, and Ro constants. Among the findings are the facts that π-donating substituents correlate well, while π-accepting substituents do not. Indications of the relative sensitivities of hydrocarbon frameworks to substituent electrostatic and resonance effects are analyzed. Photoelectron spectroscopy and carbon-13 chemical shift data of the substituted olefinic compounds are also examined to provide further insights.

Included in

Chemistry Commons



To view the content in your browser, please download Adobe Reader or, alternately,
you may Download the file to your hard drive.

NOTE: The latest versions of Adobe Reader do not support viewing PDF files within Firefox on Mac OS and if you are using a modern (Intel) Mac, there is no official plugin for viewing PDF files within the browser window.