DC Field | Value | Language |
---|---|---|
dc.contributor.author | Cho, SJ | - |
dc.contributor.author | Cui, CZ | - |
dc.contributor.author | Lee, JY | - |
dc.contributor.author | Park, JK | - |
dc.contributor.author | Suh, SB | - |
dc.contributor.author | Park, J | - |
dc.contributor.author | Kim, BH | - |
dc.contributor.author | Kim, KS | - |
dc.date.accessioned | 2016-03-31T14:10:56Z | - |
dc.date.available | 2016-03-31T14:10:56Z | - |
dc.date.created | 2009-02-28 | - |
dc.date.issued | 1997-06-13 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.other | 1997-OAK-0000009797 | - |
dc.identifier.uri | https://oasis.postech.ac.kr/handle/2014.oak/21293 | - |
dc.description.abstract | Protonation plays an important catalytic role in amide bond hydrolysis. Although the protonation site of an amide is Still debatable, O-protonation is generally preferred to N-protonation in ordinary amides. However, N-protonation can be favored in strained molecular systems. To investigate this strain effect systematically, we studied formamide, strained N-formylazetidine, and highly strained N-formylaziridine using ab initio calculations. The electron correlation effect is found to be important in determining the protonation sites of strained amides, since it contributes to stabilize N-protonation somewhat more than O-protonation. Although O-protonation is highly favored in N-formylazetidine as well as in formamide, N-protonation is favored in N-formylaziridine in both aqueous and gas phases. In case of O-protonation, the geometries become planar even for highly strained amides. The presence of polar solvents contributes to stabilize N-protonation more than O-protonation, The planarity found in O-protonated strained amides and the nonplanarity in N-protonated strained amides would have an important bearing in enzymatic reactions as well as in asymmetric syntheses. | - |
dc.description.statementofresponsibility | X | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.relation.isPartOf | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.subject | ACYL-TRANSFER-REACTIONS | - |
dc.subject | HYDROLYSIS | - |
dc.subject | WATER | - |
dc.subject | CYCLOADDITIONS | - |
dc.subject | EQUILIBRIA | - |
dc.subject | FORMAMIDE | - |
dc.subject | ENERGIES | - |
dc.subject | ABINITIO | - |
dc.subject | SYSTEMS | - |
dc.subject | SULTAM | - |
dc.title | N-protonation vs O-protonation in strained amides: Ab initio study | - |
dc.type | Article | - |
dc.contributor.college | 화학과 | - |
dc.identifier.doi | 10.1021/jo962063z | - |
dc.author.google | Cho, SJ | - |
dc.author.google | Cui, CZ | - |
dc.author.google | Lee, JY | - |
dc.author.google | Park, JK | - |
dc.author.google | Suh, SB | - |
dc.author.google | Park, J | - |
dc.author.google | Kim, BH | - |
dc.author.google | Kim, KS | - |
dc.relation.volume | 62 | - |
dc.relation.issue | 12 | - |
dc.relation.startpage | 4068 | - |
dc.relation.lastpage | 4071 | - |
dc.contributor.id | 10075891 | - |
dc.relation.journal | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.relation.index | SCI급, SCOPUS 등재논문 | - |
dc.relation.sci | SCI | - |
dc.collections.name | Journal Papers | - |
dc.type.rims | ART | - |
dc.identifier.bibliographicCitation | JOURNAL OF ORGANIC CHEMISTRY, v.62, no.12, pp.4068 - 4071 | - |
dc.identifier.wosid | A1997XE01500047 | - |
dc.date.tcdate | 2019-01-01 | - |
dc.citation.endPage | 4071 | - |
dc.citation.number | 12 | - |
dc.citation.startPage | 4068 | - |
dc.citation.title | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.citation.volume | 62 | - |
dc.contributor.affiliatedAuthor | Park, J | - |
dc.contributor.affiliatedAuthor | Kim, BH | - |
dc.contributor.affiliatedAuthor | Kim, KS | - |
dc.identifier.scopusid | 2-s2.0-0000310239 | - |
dc.description.journalClass | 1 | - |
dc.description.journalClass | 1 | - |
dc.description.wostc | 52 | - |
dc.type.docType | Article | - |
dc.subject.keywordPlus | ACYL-TRANSFER-REACTIONS | - |
dc.subject.keywordPlus | HYDROLYSIS | - |
dc.subject.keywordPlus | WATER | - |
dc.subject.keywordPlus | CYCLOADDITIONS | - |
dc.subject.keywordPlus | EQUILIBRIA | - |
dc.subject.keywordPlus | FORMAMIDE | - |
dc.subject.keywordPlus | ENERGIES | - |
dc.subject.keywordPlus | ABINITIO | - |
dc.subject.keywordPlus | SYSTEMS | - |
dc.subject.keywordPlus | SULTAM | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
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