DC Field | Value | Language |
---|---|---|
dc.contributor.advisor | Yoon-Sup Lee | - |
dc.contributor.advisor | 이윤섭 | - |
dc.contributor.author | Kim, Jong-Taek | - |
dc.contributor.author | 김종택 | - |
dc.date.accessioned | 2011-12-13T04:51:22Z | - |
dc.date.available | 2011-12-13T04:51:22Z | - |
dc.date.issued | 2006 | - |
dc.identifier.uri | http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=301345&flag=dissertation | - |
dc.identifier.uri | http://hdl.handle.net/10203/32091 | - |
dc.description | 학위논문(석사) - 한국과학기술원 : 화학과, 2006.2, [ vi, 48 p. ] | - |
dc.description.abstract | Aziridines serve as versatile building blocks for organic synthetic chemistry and play a pivotal role in biologically relevant reactions. Thus, the regioselectivity in aziridine ring-opining reaction is highly important to get a target product. Aziridines usually prefer nucleophilic attack at the less-substituted carbon (C3) due to minimal steric hindrance. Occasionally, however, there are some exceptions where the more-substituted carbon (C2) undergoes nucleophilic attack. In this study, we examined the regioselectivity of aziridine ring-opening with quantum chemical DFT calculation methods including density functional theory [B3LYP/ 6-31+G(d)]. The energy profiles of aziridine ring-opening were obtained, the activation barriers $(\Delta E^‡)$ were compared, and then the regioselectivity was determined. The analysis of reactant properties provided good explanation for regioselectivity. It was demonstrated that the unusual ring-opening occurs along the C2-N bond, activated by the concerted interaction between electron-donating aryl group and electron-withdrawing pyridine moiety. | eng |
dc.language | eng | - |
dc.publisher | 한국과학기술원 | - |
dc.subject | aziridine | - |
dc.subject | regioselectivity | - |
dc.subject | ring opening | - |
dc.subject | electronic effect | - |
dc.subject | 아지리딘 | - |
dc.subject | 자리선택성 | - |
dc.subject | 고리열림 | - |
dc.subject | 전자적 효과 | - |
dc.subject | aziridine | - |
dc.subject | regioselectivity | - |
dc.subject | ring opening | - |
dc.subject | electronic effect | - |
dc.subject | 아지리딘 | - |
dc.subject | 자리선택성 | - |
dc.subject | 고리열림 | - |
dc.subject | 전자적 효과 | - |
dc.title | Theoretical examination on the regioselective ring-opening of substituted aziridines: steric vs. electronic effect | - |
dc.title.alternative | 아지리딘 고리열림 반응의 특이한 자리선택성에 대한 이론적 연구 | - |
dc.type | Thesis(Master) | - |
dc.identifier.CNRN | 301345/325007 | - |
dc.description.department | 한국과학기술원 : 화학과, | - |
dc.identifier.uid | 020043138 | - |
dc.contributor.localauthor | Yoon-Sup Lee | - |
dc.contributor.localauthor | 이윤섭 | - |
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