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Rate and Product Studies with 1-Adamantyl Chlorothioformate under Solvolytic Conditions

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dc.contributor.authorPark, Kyoung Ho-
dc.contributor.authorSeong, Mi Hye-
dc.contributor.authorKyong, Jin Burm-
dc.contributor.authorKevill, Dennis N.-
dc.date.accessioned2023-12-11T08:30:17Z-
dc.date.available2023-12-11T08:30:17Z-
dc.date.issued2021-07-
dc.identifier.issn1661-6596-
dc.identifier.issn1422-0067-
dc.identifier.urihttps://scholarworks.bwise.kr/erica/handle/2021.sw.erica/116261-
dc.description.abstractA study was carried out on the solvolysis of 1-adamantyl chlorothioformate (1-AdSCOCl, 1) in hydroxylic solvents. The rate constants of the solvolysis of 1 were well correlated using the Grunwald-Winstein equation in all of the 20 solvents (R = 0.985). The solvolyses of 1 were analyzed as the following two competing reactions: the solvolysis ionization pathway through the intermediate (1-AdSCO)(+) (carboxylium ion) stabilized by the loss of chloride ions due to nucleophilic solvation and the solvolysis-decomposition pathway through the intermediate 1-Ad(+)Cl(-) ion pairs (carbocation) with the loss of carbonyl sulfide. In addition, the rate constants (k(exp)) for the solvolysis of 1 were separated into k through a product study and applied to the Grunwald-Winstein equation to obtain the sensitivity (m-value) to change in solvent ionizing power. For binary hydroxylic solvents, the selectivities (S) for the formation of solvolysis products were very similar to those of the 1-adamantyl derivatives discussed previously. The kinetic solvent isotope effects (KSIEs), salt effects and activation parameters for the solvolyses of 1 were also determined. These observations are compared with those previously reported for the solvolyses of 1-adamantyl chloroformate (1-AdOCOCl, 2). The reasons for change in reaction channels are discussed in terms of the gas-phase stabilities of acylium ions calculated using Gaussian 03.-
dc.format.extent13-
dc.language영어-
dc.language.isoENG-
dc.publisherMultidisciplinary Digital Publishing Institute (MDPI)-
dc.titleRate and Product Studies with 1-Adamantyl Chlorothioformate under Solvolytic Conditions-
dc.typeArticle-
dc.publisher.location스위스-
dc.identifier.doi10.3390/ijms22147394-
dc.identifier.scopusid2-s2.0-85109343617-
dc.identifier.wosid000676582300001-
dc.identifier.bibliographicCitationInternational Journal of Molecular Sciences, v.22, no.14, pp 1 - 13-
dc.citation.titleInternational Journal of Molecular Sciences-
dc.citation.volume22-
dc.citation.number14-
dc.citation.startPage1-
dc.citation.endPage13-
dc.type.docTypeArticle-
dc.description.isOpenAccessY-
dc.description.journalRegisteredClassscie-
dc.description.journalRegisteredClassscopus-
dc.relation.journalResearchAreaBiochemistry & Molecular Biology-
dc.relation.journalResearchAreaChemistry-
dc.relation.journalWebOfScienceCategoryBiochemistry & Molecular Biology-
dc.relation.journalWebOfScienceCategoryChemistry, Multidisciplinary-
dc.subject.keywordPlusTERT-BUTYL CHLORIDE-
dc.subject.keywordPlusTHIOCHLOROFORMATE ESTERS-
dc.subject.keywordPlusSN2-SN1 SPECTRUM-
dc.subject.keywordPlusCHLOROFORMATE-
dc.subject.keywordPlusMECHANISM-
dc.subject.keywordPlusKINETICS-
dc.subject.keywordPlusSCALE-
dc.subject.keywordPlusDECOMPOSITION-
dc.subject.keywordPlusHYDROLYSIS-
dc.subject.keywordPlusPATHWAYS-
dc.subject.keywordAuthor1-adamantyl chlorothioformate-
dc.subject.keywordAuthorGrunwald-Winstein equation-
dc.subject.keywordAuthorsolvolysis-
dc.subject.keywordAuthorsolvolysis-decomposition-
dc.subject.keywordAuthorionization pathway-
dc.subject.keywordAuthorcarboxylium ion-
dc.identifier.urlhttps://www.scopus.com/record/display.uri?eid=2-s2.0-85109343617&origin=inward&txGid=be2d31d4bef4252ee64536e642fc0c76#indexed-keywords-
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