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dc.contributor.authorCallejo, Ricardo
dc.contributor.authorCorr, Michael J.
dc.contributor.authorYang, Mingyan
dc.contributor.authorWang, Mingan
dc.contributor.authorCordes, David B.
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorO'Hagan, David
dc.date.accessioned2017-05-06T23:33:43Z
dc.date.available2017-05-06T23:33:43Z
dc.date.issued2016-06-06
dc.identifier.citationCallejo , R , Corr , M J , Yang , M , Wang , M , Cordes , D B , Slawin , A M Z & O'Hagan , D 2016 , ' Fluorinated musk fragrances : the CF 2 group as a conformational bias influencing the odour of civetone and ( R )-muscone ' Chemistry - A European Journal , vol. 22 , no. 24 , pp. 8137-8151 . https://doi.org/10.1002/chem.201600519en
dc.identifier.issn1521-3765
dc.identifier.otherPURE: 242457316
dc.identifier.otherPURE UUID: 119d25ab-1329-4685-9646-6a76306101b5
dc.identifier.otherBibtex: urn:c2e7e91be904a41ab31c164c6cd23f24
dc.identifier.otherScopus: 84973126819
dc.identifier.otherORCID: /0000-0002-5366-9168/work/28023978
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56862095
dc.identifier.urihttp://hdl.handle.net/10023/10717
dc.descriptionThis work was supported by the Engineering and Physical Sciences Research Council (EPSRC) and the European Research Council (ERC). The authors acknowledge the EPSRC National Mass Spectrometry Facility (Swansea). M.Y. thanks the China Scholarship Council for financial support. D.O'H. thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstractThe difluoromethylene (CF2) group has a strong tendency to adopt corner over edge locations in aliphatic macrocycles. In this study, the CF2 group has been introduced into musk relevant macrocyclic ketones. Nine civetone and five muscone analogues have been prepared by synthesis for structure and odour comparisons. X-ray studies indeed show that the CF2 groups influence ring structure and they give some insight into the preferred ring conformations, triggering a musk odour as determined in a professional perfumery environment. The historical conformational model of Bersuker and co-workers for musk fragrance generally holds, and structures that become distorted from this consensus, by the particular placement of the CF2 groups, lose their musk fragrance and become less pleasant.
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.rights© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1002/chem.201600519en
dc.subjectConformation analysisen
dc.subjectMacrocyclesen
dc.subjectMusk fragrancesen
dc.subjectOrganofluorine chemistryen
dc.subjectStructure–activity relationshipsen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleFluorinated musk fragrances : the CF2 group as a conformational bias influencing the odour of civetone and (R)-musconeen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews.Biomedical Sciences Research Complexen
dc.identifier.doihttps://doi.org/10.1002/chem.201600519
dc.description.statusPeer revieweden
dc.date.embargoedUntil2017-05-06


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