dc.contributor.author | Lorentzen, Marianne | |
dc.contributor.author | Kalvet, Indrek | |
dc.contributor.author | Sauriol, Francoise | |
dc.contributor.author | Rantanen, Toni | |
dc.contributor.author | Jørgensen, Kåre Bredeli | |
dc.contributor.author | Snieckus, Victor | |
dc.date.accessioned | 2022-12-22T15:51:47Z | |
dc.date.available | 2022-12-22T15:51:47Z | |
dc.date.created | 2017-12-23T13:25:14Z | |
dc.date.issued | 2017 | |
dc.identifier.citation | Lorentzen, M., Kalvet, I., Sauriol, F., Rantanen, T., Jørgensen, K. B., & Snieckus, V. (2017). Atropisomerism in tertiary biaryl 2-amides: a study of Ar–CO and Ar–Ar′ rotational barriers. The Journal of Organic Chemistry, 82(14), 7300-7308. | en_US |
dc.identifier.issn | 0022-3263 | |
dc.identifier.uri | https://hdl.handle.net/11250/3039291 | |
dc.description.abstract | A rotational barrier study was performed on eight tertiary biaryl 2-amides using variable temperature (VT) NMR and exchange (EXSY) spectroscopy experiments. Seven out of the eight 2-amido-2′-methylbiphenyls with additional 3- and 6-substitution patterns (1-7) were found to have approximately similar rotational barriers (G‡ Tc= 56.5 – 67.5 kJ/mol). However, for both 3- and 6-substitution (8), the rotational barrier was found to be significantly higher (G‡ = 102.6-103.8 kJ/mol). Computational studies performed on all eight compounds gave results in good agreement with the experimental rotational barriers. A transition state in which atropisomerism occurs by a cooperative rotation of the Ar-CO and Ar-Ar′ bonds depending on substituent location is proposed. | en_US |
dc.language.iso | eng | en_US |
dc.title | Atropisomerism in Tertiary Biaryl 2-Amides: A Study of Ar-CO and Ar-Ar? Rotational Barriers | en_US |
dc.type | Peer reviewed | en_US |
dc.type | Journal article | en_US |
dc.description.version | acceptedVersion | en_US |
dc.rights.holder | The authors | en_US |
dc.subject.nsi | VDP::Matematikk og Naturvitenskap: 400 | en_US |
dc.source.pagenumber | 7300-7308 | en_US |
dc.source.volume | 82 | en_US |
dc.source.journal | Journal of Organic Chemistry | en_US |
dc.source.issue | 14 | en_US |
dc.identifier.doi | 10.1021/acs.joc.7b00890 | |
dc.identifier.cristin | 1531777 | |
cristin.unitcode | 217,2,0,0 | |
cristin.unitcode | 217,8,2,0 | |
cristin.unitname | Forsknings- og innovasjonsavdelingen | |
cristin.unitname | Institutt for matematikk og naturvitenskap | |
cristin.ispublished | true | |
cristin.fulltext | postprint | |
cristin.qualitycode | 2 | |