Reactivity studies of phosphoric amides and esters

 

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dc.contributor.advisor Modro, Tomasz A en_ZA
dc.contributor.author Davidowitz, Bette en_ZA
dc.date.accessioned 2016-10-24T03:50:36Z
dc.date.available 2016-10-24T03:50:36Z
dc.date.issued 1984 en_ZA
dc.identifier.citation Davidowitz, B. 1984. Reactivity studies of phosphoric amides and esters. University of Cape Town. en_ZA
dc.identifier.uri http://hdl.handle.net/11427/22276
dc.description Bibliography: pages 154-161. en_ZA
dc.description.abstract The effect of protonation and Lewis acid-base interaction on the ¹H n.m.r. chemical shifts of the ester and amide bonds in selected phosphoramidates (RO)₂P(O)NR'₂ was investigated. The results are interpreted in terms of the interaction of the phosphoryl oxygen atom with Lewis acids and oxygen/nitrogen diprotonation in trifluoromethanesulphonic acid. Intramolecular nucleophilic displacement of the halide ion from secondary β-chloroethyl-substituted phosphoramidates X₂P(O)NHCH₂CH₂Cl, diamidates (RO) (MeNH)P(O)NHCH₂CH₂Cl and β-chloroethyl phosphates Y(MeO)P(O)OCH₂CH₂Cl, was studied under conditions of electrophilic (Ag+) and basic (NaH) catalysis. 1,3-Substitution by the nitrogen atom of the phosphdramidates, yielding ethylenimine derivatives was found to be the preferred reaction-pathway; the alternative 1,5-reaction involving the amide nittogen or phosphoryl oxygen atoms was not observed. No intramolecular nucleophilic displacement occurred in the β-chloroethyl phosphate esters. en_ZA
dc.language.iso eng en_ZA
dc.subject.other Chemistry en_ZA
dc.title Reactivity studies of phosphoric amides and esters en_ZA
dc.type Doctoral Thesis
uct.type.publication Research en_ZA
uct.type.resource Thesis en_ZA
dc.publisher.institution University of Cape Town
dc.publisher.faculty Faculty of Science en_ZA
dc.publisher.department Department of Chemistry en_ZA
dc.type.qualificationlevel Doctoral
dc.type.qualificationname PhD en_ZA
uct.type.filetype Text
uct.type.filetype Image
dc.identifier.apacitation Davidowitz, B. (1984). <i>Reactivity studies of phosphoric amides and esters</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/22276 en_ZA
dc.identifier.chicagocitation Davidowitz, Bette. <i>"Reactivity studies of phosphoric amides and esters."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 1984. http://hdl.handle.net/11427/22276 en_ZA
dc.identifier.vancouvercitation Davidowitz B. Reactivity studies of phosphoric amides and esters. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 1984 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/22276 en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Davidowitz, Bette AB - The effect of protonation and Lewis acid-base interaction on the ¹H n.m.r. chemical shifts of the ester and amide bonds in selected phosphoramidates (RO)₂P(O)NR'₂ was investigated. The results are interpreted in terms of the interaction of the phosphoryl oxygen atom with Lewis acids and oxygen/nitrogen diprotonation in trifluoromethanesulphonic acid. Intramolecular nucleophilic displacement of the halide ion from secondary β-chloroethyl-substituted phosphoramidates X₂P(O)NHCH₂CH₂Cl, diamidates (RO) (MeNH)P(O)NHCH₂CH₂Cl and β-chloroethyl phosphates Y(MeO)P(O)OCH₂CH₂Cl, was studied under conditions of electrophilic (Ag+) and basic (NaH) catalysis. 1,3-Substitution by the nitrogen atom of the phosphdramidates, yielding ethylenimine derivatives was found to be the preferred reaction-pathway; the alternative 1,5-reaction involving the amide nittogen or phosphoryl oxygen atoms was not observed. No intramolecular nucleophilic displacement occurred in the β-chloroethyl phosphate esters. DA - 1984 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 1984 T1 - Reactivity studies of phosphoric amides and esters TI - Reactivity studies of phosphoric amides and esters UR - http://hdl.handle.net/11427/22276 ER - en_ZA


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