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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.identifier4638426
dc.identifiercbd729cb-598f-4a5f-92be-417385c017d3
dc.identifier000280216400030
dc.identifier77954129828
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.otherORCID: /0000-0002-1095-7143/work/48131739
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861611
dc.identifier.otherORCID: /0000-0002-1498-9652/work/31779249
dc.identifier.urihttps://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.format.extent745728
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
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.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.doi10.1002/chem.201000435
dc.description.statusPeer revieweden


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