DC Field | Value | Language |
---|---|---|
dc.contributor.author | Lee, JC | ko |
dc.contributor.author | Koh, HY | ko |
dc.contributor.author | Chang, MH | ko |
dc.contributor.author | Lee, Yoon Sup | ko |
dc.date.accessioned | 2013-03-02T19:48:22Z | - |
dc.date.available | 2013-03-02T19:48:22Z | - |
dc.date.created | 2012-02-06 | - |
dc.date.created | 2012-02-06 | - |
dc.date.issued | 1996-07 | - |
dc.identifier.citation | BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.17, no.7, pp.604 - 607 | - |
dc.identifier.issn | 0253-2964 | - |
dc.identifier.uri | http://hdl.handle.net/10203/75232 | - |
dc.description.abstract | Semiempirical PM3 MO calculations are applied to estimate both 1-atom (X=S, O, C) and 3-substituent CY=R, CH(2)R, SR, CH(2)SR) effects on the reactions of some 1-atom-replaced and 3-substituted cephem-like beta-lactam compounds of thiacephems, oxacephems, and carbacephems. Stabilization energy (SE) of the reaction intermediate for the reaction with a hydroxyl ion can be used to evaluate the facility of a reaction and selected as a chemical reactivity index. With the 1-atom effect only, the SE values obtained imply that thiacephems are generally more reactive than the other two cephem-like molecules and the reactivity order is thiacephems>oxacephems>carbacephems. When it comes to the 3-substituent (Y=R, CH(2)R, SR, CH(2)SR) effect, chemical reactivity can be best realized by using a 3-substituted thiacephem molecule capable of giving a resonance-stabilized and electron-rich leaving group after the reaction with a nucleophile. SE values, however, decrease in most cases when an additional intervening ethylene group is present (Y=CH(2)R, CH(2)SR). The overall 3-substituent reactivity tendency is SR>CH(2)SR>R>CH(2)R. | - |
dc.language | English | - |
dc.publisher | KOREAN CHEMICAL SOC | - |
dc.subject | ANTIBIOTICS | - |
dc.subject | MECHANISMS | - |
dc.title | Semiempirical calculations of substituent effects on the reactions of cephem-like beta-lactam molecules | - |
dc.type | Article | - |
dc.identifier.wosid | A1996VA12300013 | - |
dc.identifier.scopusid | 2-s2.0-18444367117 | - |
dc.type.rims | ART | - |
dc.citation.volume | 17 | - |
dc.citation.issue | 7 | - |
dc.citation.beginningpage | 604 | - |
dc.citation.endingpage | 607 | - |
dc.citation.publicationname | BULLETIN OF THE KOREAN CHEMICAL SOCIETY | - |
dc.contributor.localauthor | Lee, Yoon Sup | - |
dc.contributor.nonIdAuthor | Lee, JC | - |
dc.contributor.nonIdAuthor | Koh, HY | - |
dc.contributor.nonIdAuthor | Chang, MH | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | ANTIBIOTICS | - |
dc.subject.keywordPlus | MECHANISMS | - |
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