The Effect of the ortho Nitro Group in the Solvolysis of Benzyl and Benzoyl Halides
DC Field | Value | Language |
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dc.contributor.author | Park, Kyoung-Ho | - |
dc.contributor.author | Rhu, Chan Joo | - |
dc.contributor.author | Kyong, Jin Burm | - |
dc.contributor.author | Kevill, Dennis N. | - |
dc.date.accessioned | 2021-06-22T09:42:46Z | - |
dc.date.available | 2021-06-22T09:42:46Z | - |
dc.date.created | 2021-01-21 | - |
dc.date.issued | 2019-08 | - |
dc.identifier.issn | 1661-6596 | - |
dc.identifier.uri | https://scholarworks.bwise.kr/erica/handle/2021.sw.erica/2383 | - |
dc.description.abstract | A kinetic study was carried out on the solvolysis of o-nitrobenzyl bromide (o-isomer, 1) and p-nitrobenzyl bromide (p-isomer, 3), and o-nitrobenzoyl chloride (o-isomer, 2) in a wide range of solvents under various temperatures. In all of the solvents without aqueous fluoroalcohol, the reactions of 1 were solvolyzed at a similar rate to those observed for 3, and the reaction rates of 2 were about ten times slower than those of the previously studied p-nitrobenzoyl chloride (p-isomer, 4). For solvolysis in aqueous fluoroalcohol, the reactivity of 2 was kinetically more reactive than 4. The l/m values of the extended Grunwald-Winstein (G-W) equation for solvolysis of 1 and 2 in solvents without fluoroalcohol content are all significantly larger than unity while those in all the fluoroalcohol solvents are less than unity. The role of the ortho-nitro group as an intramolecular nucleophilic assistant (internal nucleophile) in the solvolytic reaction of 1 and 2 was discussed. The results are also compared with those reported earlier for o-carbomethoxybenzyl bromide (5) and o-nitrobenzyl p-toluenesulfonate (7). From the product studies and the activation parameters for solvolyses of 1 and 2 in several organic hydroxylic solvents, mechanistic conclusions are drawn. | - |
dc.language | 영어 | - |
dc.language.iso | en | - |
dc.publisher | Multidisciplinary Digital Publishing Institute (MDPI) | - |
dc.title | The Effect of the ortho Nitro Group in the Solvolysis of Benzyl and Benzoyl Halides | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Park, Kyoung-Ho | - |
dc.identifier.doi | 10.3390/ijms20164026 | - |
dc.identifier.scopusid | 2-s2.0-85071336326 | - |
dc.identifier.wosid | 000484411100183 | - |
dc.identifier.bibliographicCitation | International Journal of Molecular Sciences, v.20, no.16, pp.1 - 12 | - |
dc.relation.isPartOf | International Journal of Molecular Sciences | - |
dc.citation.title | International Journal of Molecular Sciences | - |
dc.citation.volume | 20 | - |
dc.citation.number | 16 | - |
dc.citation.startPage | 1 | - |
dc.citation.endPage | 12 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.isOpenAccess | Y | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Biochemistry & Molecular Biology | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Biochemistry & Molecular Biology | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.subject.keywordPlus | INTRAMOLECULAR NUCLEOPHILIC PARTICIPATION | - |
dc.subject.keywordPlus | TERT-BUTYL CHLORIDE | - |
dc.subject.keywordPlus | SN2-SN1 SPECTRUM | - |
dc.subject.keywordPlus | P-NITROBENZYL | - |
dc.subject.keywordPlus | RATES | - |
dc.subject.keywordPlus | SCALE | - |
dc.subject.keywordPlus | CHLOROFORMATE | - |
dc.subject.keywordPlus | DERIVATIVES | - |
dc.subject.keywordPlus | BENZHYDRYL | - |
dc.subject.keywordPlus | ASSISTANCE | - |
dc.subject.keywordAuthor | o-nitrobenzyl bromide | - |
dc.subject.keywordAuthor | o-nitrobenzoyl chloride | - |
dc.subject.keywordAuthor | ortho nitro group | - |
dc.subject.keywordAuthor | Grunwald-Winstein equation | - |
dc.subject.keywordAuthor | intramolecular nucleophilic assistance | - |
dc.subject.keywordAuthor | solvolysis | - |
dc.subject.keywordAuthor | nucleophilicity | - |
dc.subject.keywordAuthor | ionizing power | - |
dc.identifier.url | https://www.mdpi.com/1422-0067/20/16/4026 | - |
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