Hindered C-N bond rotation in triazinyl dithiocarbamates
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Jung, Taesub | - |
dc.contributor.author | Do, Hee-Jin | - |
dc.contributor.author | Son, Jongwoo | - |
dc.contributor.author | Song, Jae Hee | - |
dc.contributor.author | Cha, Wansik | - |
dc.contributor.author | Kim, Yeong-Joon | - |
dc.contributor.author | Lee, Kyung-Koo | - |
dc.contributor.author | Kwak, Kyungwon | - |
dc.date.accessioned | 2021-09-02T16:09:34Z | - |
dc.date.available | 2021-09-02T16:09:34Z | - |
dc.date.created | 2021-06-16 | - |
dc.date.issued | 2018-01-15 | - |
dc.identifier.issn | 0022-2860 | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/77970 | - |
dc.description.abstract | The substituent and solvent effects on the rotation around a C-N amide bond were studied for a series of triazine dibenzylcarbamodithioates. The Gibbs free energies (Delta G(double dagger)) were measured to be 16-18 kcal/mol in DMSO-d(6) and toluene-d(8) using variable-temperature nuclear magnetic resonance (VT-H-1 NMR) spectroscopy. Density functional theory (DFT) calculations reproduced the experimental observations with various substituents, as well as solvents. From the detailed analysis of the DFT results, we found that the electron donating dibenzyl amine group increased the electron population on the triazinyl ring, which decreased the rotational barrier of the C-N bond in the dithiocarbamate group attached to the triazinyl ring. The higher electron population on the triazine moiety stabilizes the partial double bond character of the S-C bond, which competitively excludes the double bond character of the C-N bond. Therefore, the rotational dynamics of the C-N bond in dithiocarbamates can be a sensitive probe to small differences in the electron population of substituents on sulfur. (c) 2017 Elsevier B.V. All rights reserved. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | ELSEVIER SCIENCE BV | - |
dc.subject | TRIBOLOGICAL BEHAVIORS | - |
dc.subject | DERIVATIVES | - |
dc.subject | ADDITIVES | - |
dc.subject | OIL | - |
dc.subject | EXCHANGE | - |
dc.subject | BARRIER | - |
dc.title | Hindered C-N bond rotation in triazinyl dithiocarbamates | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Kwak, Kyungwon | - |
dc.identifier.doi | 10.1016/j.molstruc.2017.09.063 | - |
dc.identifier.scopusid | 2-s2.0-85030163023 | - |
dc.identifier.wosid | 000415774400023 | - |
dc.identifier.bibliographicCitation | JOURNAL OF MOLECULAR STRUCTURE, v.1152, pp.215 - 222 | - |
dc.relation.isPartOf | JOURNAL OF MOLECULAR STRUCTURE | - |
dc.citation.title | JOURNAL OF MOLECULAR STRUCTURE | - |
dc.citation.volume | 1152 | - |
dc.citation.startPage | 215 | - |
dc.citation.endPage | 222 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Physical | - |
dc.subject.keywordPlus | TRIBOLOGICAL BEHAVIORS | - |
dc.subject.keywordPlus | DERIVATIVES | - |
dc.subject.keywordPlus | ADDITIVES | - |
dc.subject.keywordPlus | OIL | - |
dc.subject.keywordPlus | EXCHANGE | - |
dc.subject.keywordPlus | BARRIER | - |
dc.subject.keywordAuthor | C-N bond rotational dynamics | - |
dc.subject.keywordAuthor | VT-NMR | - |
dc.subject.keywordAuthor | DFT calculation | - |
dc.subject.keywordAuthor | Triazinyl derivative | - |
dc.subject.keywordAuthor | Dithiocarbamate | - |
Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.
(02841) 서울특별시 성북구 안암로 14502-3290-1114
COPYRIGHT © 2021 Korea University. All Rights Reserved.
Certain data included herein are derived from the © Web of Science of Clarivate Analytics. All rights reserved.
You may not copy or re-distribute this material in whole or in part without the prior written consent of Clarivate Analytics.