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dc.contributor.authorKnight, Fergus Ross
dc.contributor.authorFuller, Amy
dc.contributor.authorBuehl, Michael
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorWoollins, J Derek
dc.date.accessioned2016-01-15T15:40:07Z
dc.date.available2016-01-15T15:40:07Z
dc.date.issued2010-07-05
dc.identifier.citationKnight , F R , Fuller , A , Buehl , M , Slawin , A M Z & Woollins , J D 2010 , ' Synthetic and structural studies of 1-halo-8-(alkylchalcogeno)naphthalene derivatives ' Chemistry - A European Journal , vol. 16 , no. 25 , pp. 7605-7616 . https://doi.org/10.1002/chem.201000435en
dc.identifier.issn0947-6539
dc.identifier.otherPURE: 4638426
dc.identifier.otherPURE UUID: cbd729cb-598f-4a5f-92be-417385c017d3
dc.identifier.otherWOS: 000280216400030
dc.identifier.otherScopus: 77954129828
dc.identifier.otherORCID: /0000-0002-1095-7143/work/48131739
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861611
dc.identifier.urihttp://hdl.handle.net/10023/8030
dc.descriptionThis work is funded by the EPSRCen
dc.description.abstractA series of eight 1-halo-8-(alkylchalcogeno)naphthalene derivatives ( 1 – 8 ; halogen=Br, I; alkylchalcogen=SEt, SPh, SePh, TePh) containing a halogen and a chalcogen atom occupying the peri positions have been prepared and fully characterised by using X-ray crystallography, multinuclear NMR spectroscopy, IR spectroscopy and MS. Naphthalene distortion due to non-covalent substituent interactions was studied as a function of the bulk of the interacting chalcogen atoms and the size and nature of the alkyl group attached to them. X-ray data for 1 , 2 , 4 and 5 – 8 were compared. Molecular structures were analysed in terms of naphthalene ring torsions, peri-atom displacement, splay angle magnitude, X⋅⋅⋅E interactions, aromatic ring orientations and quasi-linear X⋅⋅⋅EC arrangements. A general increase in the X⋅⋅⋅E distance was observed for molecules that contain bulkier atoms at the peri positions. The I⋅⋅⋅S distance of 4 is comparable with the I⋅⋅⋅Te distance of 8 , and is ascribed to a stronger lone pair–lone pair repulsion due to the presence of an axial S(naphthyl) ring conformation. Density functional theory (B3LYP) calculations performed on 5 – 8 revealed Wiberg bond index values of 0.05–0.08, which indicate minor interactions taking place between the non-bonded atoms in these compounds.
dc.format.extent12
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.rightsCopyright © 2010 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.201000435en
dc.subjectChalcogensen
dc.subjectDensity functional calculationsen
dc.subjectHalogensen
dc.subjectNaphthaleneen
dc.subjectperi-Substitutionen
dc.subjectX-ray diffractionen
dc.subjectNMR chemical-shiftsen
dc.subjectPentacoordinate disilanes bearingen
dc.subjectPolyaromatic hydrocarbon ligandsen
dc.subjectNaphthalene peri positionsen
dc.subject4-center 6-electron bonden
dc.subjectRay-diffraction dataen
dc.subjectCENTER-DOT-Pen
dc.subjectX-RAYen
dc.subjectCation radicalsen
dc.subjectSubstituted naphthalenesen
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titleSynthetic and structural studies of 1-halo-8-(alkylchalcogeno)naphthalene derivativesen
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.Office of the Principalen
dc.identifier.doihttps://doi.org/10.1002/chem.201000435
dc.description.statusPeer revieweden


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