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Jack McLean FINAL Thesis__final format approved LW 8-3-2023.pdf (1.15 MB)

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Abstract Header

Comparison of the Acidity of Natural and Synthetic Polyenes and the Characterization of the Proposed Structures of Conjugated Protonated Products

McLean, Jack Brian
http://orcid.org/0009-0000-6000-6787
http://rave.ohiolink.edu/etdc/view?acc_num=dayton1691402800246123

Abstract Details

2023, Master of Science (M.S.), University of Dayton, Chemistry.
Linear polyenes are an important class of compounds containing two or more alternating carbon-carbon double and single bonds that are soluble in organic non-polar solvents. Determining the relative basicity of polyenes experimentally is challenging in practice because such studies require mixing non-polar polyene-organic solvent mixtures with high concentrations of moderately polar organic acids. We will present computational approaches to determining the basicity of trans-1,4-diphenyl-1,3-butadiene (DPB), all trans-1,6-diphenyl-1,3,5-hexatriene (DPH), or all trans-1,8-diphenyl-1,3,5,7-octatetraene (DPO) with trifluoroacetic acid (TFAH) in n-hexane, benzene, and chloroform solvents. Our calculations indicate that the basicities of the DPPs increase with increasing length of the polyene moiety (DPO > DPH >> DPB) in the gas phase and in both benzene and nā€“heptane solvents. We will also show a comparison of the computational basicities of the various secondary and tertiary protonation sites along the conjugation pathway of š¯›½-carotene, at natural terpenoid polyene, to the synthetic polyenes. Finally, this thesis will offer preliminary chemical mechanisms for the formation of the numerous products resulting from the rearrangements of the carbocations generated as a result of protonation. These mechanisms are proposed based on the final structures of the numerous isolated byproducts from this reaction using GC-MS, IR and 1D/2D NMR spectroscopies.
Justin Biffinger (Advisor)
Mark Masthay (Advisor)
Shawn Swavey (Committee Member)
49 p.
Chemistry; Organic Chemistry; Physical Chemistry
Trifluoroacetic acid Diphenylpolyenes Cyclization Dimerization Adduct

Recommended Citations

Citations

  • McLean, J. B. (2023). Comparison of the Acidity of Natural and Synthetic Polyenes and the Characterization of the Proposed Structures of Conjugated Protonated Products [Master's thesis, University of Dayton]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=dayton1691402800246123

    APA Style (7th edition)

  • McLean, Jack. Comparison of the Acidity of Natural and Synthetic Polyenes and the Characterization of the Proposed Structures of Conjugated Protonated Products . 2023. University of Dayton, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=dayton1691402800246123.

    MLA Style (8th edition)

  • McLean, Jack. "Comparison of the Acidity of Natural and Synthetic Polyenes and the Characterization of the Proposed Structures of Conjugated Protonated Products ." Master's thesis, University of Dayton, 2023. http://rave.ohiolink.edu/etdc/view?acc_num=dayton1691402800246123

    Chicago Manual of Style (17th edition)

dayton1691402800246123
57
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This open access ETD is published by University of Dayton and OhioLINK.