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Quantum Chemical pKa Estimation of Carbon Acids, Saturated Alcohols, and Ketones via Quantitative Structure-Activity Relationships

Baldasare, Corey Adam
http://rave.ohiolink.edu/etdc/view?acc_num=wright1598550823525731

Abstract Details

2020, Master of Science (MS), Wright State University, Chemistry.
Acid dissociation constants, often expressed as pKa values, afford vital information with regards to molecular behavior in various environments and are of significance in fields of organic, inorganic, and medicinal chemistry. Several quantitative structure-activity relationships (QSARs) were developed that correlate experimental pKas for a given class of compounds with a descriptor(s) calculated using density functional theory at the B3LYP/6-31+G** level utilizing the CPCM solvent model. A set of carbon acids provided a good final QSAR model of experimental aqueous pKas versus ΔEH2O (R2 = 0.9647) upon removal of three aldehydes as outliers. A study of saturated alcohols offered a final QSAR model with R2 = 0.9594, which was employed to confirm the behavior of the three aldehydes as hydrated species in aqueous solution. Finally, a study restricted to ketones was conducted to estimate their pKas in dimethyl sulfoxide solution. QSAR models of experimental pKas versus ΔEDMSO for the keto and enol tautomers were modest at best (R2 = 0.8477 and 0.7694, respectively). A binary linear regression was employed to incorporate descriptors representing both the keto and enol tautomers, improving the final R2 to 0.9670 upon removal of one outlier. The QSAR models presented may be utilized to estimate pKas for related compounds not offered in the existing literature or that are challenging to measure experimentally.
Paul Seybold, Ph.D. (Advisor)
Eric Fossum, Ph.D. (Committee Member)
David Dolson, Ph.D. (Committee Member)
99 p.
Chemistry; Organic Chemistry; Physical Chemistry
QSAR; structure activity relationship; pKa; acid dissociation constants; density functional theory; DFT; carbon acids; hydrocarbons; saturated alcohols; aldehydes; ketones; theoretical keto-enol tautomerism

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Citations

  • Baldasare, C. A. (2020). Quantum Chemical pKa Estimation of Carbon Acids, Saturated Alcohols, and Ketones via Quantitative Structure-Activity Relationships [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1598550823525731

    APA Style (7th edition)

  • Baldasare, Corey. Quantum Chemical pKa Estimation of Carbon Acids, Saturated Alcohols, and Ketones via Quantitative Structure-Activity Relationships. 2020. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1598550823525731.

    MLA Style (8th edition)

  • Baldasare, Corey. "Quantum Chemical pKa Estimation of Carbon Acids, Saturated Alcohols, and Ketones via Quantitative Structure-Activity Relationships." Master's thesis, Wright State University, 2020. http://rave.ohiolink.edu/etdc/view?acc_num=wright1598550823525731

    Chicago Manual of Style (17th edition)

wright1598550823525731
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This open access ETD is published by Wright State University and OhioLINK.