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Dibenzothiophene S-oxide and Derivatives as Atomic Oxygen Precursors and Applications for the Study of Sulfenic Acids
Başlık:
Dibenzothiophene S-oxide and Derivatives as Atomic Oxygen Precursors and Applications for the Study of Sulfenic Acids
Yazar:
Omlid, Sara M., author.
ISBN:
9780438127463
Yazar Ek Girişi:
Fiziksel Tanımlama:
1 electronic resource (219 pages)
Genel Not:
Source: Dissertation Abstracts International, Volume: 79-11(E), Section: B.
Advisors: Ryan D. McCulla Committee members: Dana A. Baum; Paul J. Bracher; David A. Ford; Paul A. Jelliss.
Özet:
In this dissertation, dibenzothiophene S-oxide (DBTO) is evaluated as a photoactivatable atomic oxygen [O(3P)] precursor and further studied for potential applications. To begin, the mechanism of photodeoxygenation of DBTO is investigated with a conclusion that O(3P) is the resulting oxidant. In a second study, various methods for synthesizing water-soluble DBTO derivatives are evaluated. In this study, the synthesis of DBTO disulfonic acid derivatives is reported. It is concluded that a direct sulfonation approach gives the best yields, while a modular approach allows for exceedingly high purities. In a third study, using DBTO as an O(3P)-precursor, the reactivity of O(3P) with various functional groups in the condensed phase is explored, and thiols are shown to be the most reactive. Additionally, an interesting phenomenon affecting the kinetics of oxidations where DBTO is used as an O(3P)-precursor is reported; the phenomenon involves reactions occurring within the solvent cage in which O(3P) is produced and is an effect that is amplified by sulfoxide-alcohol hydrogen bonding. In conclusion, DBTO is an excellent photoactivatable O(3P)-precursor and has potential for applications in biological systems, specifically for the selective oxidation of protein thiols.
Notlar:
School code: 0193
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Yer Numarası | Demirbaş Numarası | Shelf Location | Lokasyon / Statüsü / İade Tarihi |
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XX(692717.1) | 692717-1001 | Proquest E-Tez Koleksiyonu | Arıyor... |
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