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Reactivity studies of phosphoric amides and esters
Bibliography: pages 154-161.
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| Other Authors: | |
| Format: | Thesis |
| Language: | English |
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Department of Chemistry
2016
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| _version_ | 1867613225360556032 |
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| access_status_str | Open Access |
| author | Davidowitz, Bette |
| author2 | Modro, Tomasz A |
| author_browse | Davidowitz, Bette Modro, Tomasz A |
| author_facet | Modro, Tomasz A Davidowitz, Bette |
| author_sort | Davidowitz, Bette |
| collection | Thesis |
| description | Bibliography: pages 154-161. |
| format | Thesis |
| id | oai:open.uct.ac.za:11427/22276 |
| institution | University of Cape Town (South Africa) |
| language | eng |
| last_indexed | 2026-06-10T12:32:45.765Z |
| license_str | Not specified — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UCTD — University of Cape Town Open Access Repository |
| publishDate | 2016 |
| publishDateRange | 2016 |
| publishDateSort | 2016 |
| publisher | Department of Chemistry |
| publisherStr | Department of Chemistry |
| record_format | dspace |
| source_str | UCTD — University of Cape Town Open Access Repository |
| spelling | oai:open.uct.ac.za:11427/22276 Reactivity studies of phosphoric amides and esters Davidowitz, Bette Modro, Tomasz A Chemistry Bibliography: pages 154-161. 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. 2016-10-24T03:50:36Z 2016-10-24T03:50:36Z 1984 Doctoral Thesis Doctoral PhD http://hdl.handle.net/11427/22276 eng application/pdf Department of Chemistry Faculty of Science University of Cape Town |
| spellingShingle | Chemistry Davidowitz, Bette Reactivity studies of phosphoric amides and esters |
| thesis_degree_str | Doctoral |
| title | Reactivity studies of phosphoric amides and esters |
| title_full | Reactivity studies of phosphoric amides and esters |
| title_fullStr | Reactivity studies of phosphoric amides and esters |
| title_full_unstemmed | Reactivity studies of phosphoric amides and esters |
| title_short | Reactivity studies of phosphoric amides and esters |
| title_sort | reactivity studies of phosphoric amides and esters |
| topic | Chemistry |
| url | http://hdl.handle.net/11427/22276 |
| work_keys_str_mv | AT davidowitzbette reactivitystudiesofphosphoricamidesandesters |