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dc.contributor.authorWang, Yi
dc.contributor.authorCallejo, Ricardo
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorO'Hagan, David
dc.date.accessioned2014-07-09T14:31:02Z
dc.date.available2014-07-09T14:31:02Z
dc.date.issued2014-01-06
dc.identifier.citationWang , Y , Callejo , R , Slawin , A M Z & O'Hagan , D 2014 , ' The difluoromethylene (CF 2 ) group in aliphatic chains : synthesis and conformational preference of palmitic acids and nonadecane containing CF 2 groups ' , Beilstein Journal of Organic Chemistry , vol. 10 , pp. 18-25 . https://doi.org/10.3762/bjoc.10.4en
dc.identifier.issn1860-5397
dc.identifier.otherPURE: 111957840
dc.identifier.otherPURE UUID: f59f45d5-6e71-4780-a957-bec7be884e34
dc.identifier.otherWOS: 000329819900002
dc.identifier.otherScopus: 84891908587
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861500
dc.identifier.otherWOS: 000329819900002
dc.identifier.otherORCID: /0000-0002-0510-5552/work/68281223
dc.identifier.urihttp://hdl.handle.net/10023/4990
dc.descriptionFunding: ERC Advanced Investigator Grant (D.O'H).en
dc.description.abstractThe syntheses of palmitic acids and a nonadecane are reported with CF2 groups located 1,3 or 1,4 to each other along the aliphatic chain. Specifically 8,8,10,10- and 8,8,11,11-tetrafluorohexadecanoic acids (6b and 6c) are prepared as well as the singly modified analogue 8,8-difluorohexadecanoic acid (6a). Also 8,8,11,11-tetrafluorononadecane (27) is prepared as a pure hydrocarbon containing a 1,4-di-CF2 motif. The modified palmitic acids are characterized by differential scanning calorimetry (DSC) to determine melting points and phase behaviour relative to palmitic acid (62.5 degrees C). It emerges that 6c, with the CF2 groups placed 1,4- to each other, has a significantly higher melting point (89.9 degrees C) when compared to the other analogues and palmitic acid itself. It is a crystalline compound and the structure reveals an extended anti-zig-zag chain. Similarly 8,8,11,11-tetrafluorononadecane (27) adopts an extended anti-zig-zag structure. This is rationalized by dipolar relaxation between the two CF2 groups placed 1,4 to each other in the extended anti-zig-zag chain and suggests a design modification for long chain aliphatics which can introduce conformational stability.
dc.format.extent8
dc.language.isoeng
dc.relation.ispartofBeilstein Journal of Organic Chemistryen
dc.rights© 2014 Wang et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)en
dc.rights© 2014 Wang et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)en
dc.subjectDifluoromethyleneen
dc.subjectFatty acidsen
dc.subjectFluorinationen
dc.subjectOrganic fluorine chemistryen
dc.subjectOrgano-fluorineen
dc.subjectPalmitic aciden
dc.subjectC-F Bbonden
dc.subjectOrganofluorine chemistryen
dc.subjectOrganic-compoundsen
dc.subjectFlourineen
dc.subjectDerivativesen
dc.subjectReagentsen
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titleThe difluoromethylene (CF2) group in aliphatic chains : synthesis and conformational preference of palmitic acids and nonadecane containing CF2 groupsen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.description.versionPublisher PDFen
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/10.3762/bjoc.10.4
dc.description.statusPeer revieweden
dc.identifier.urlhttp://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-10-4en


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