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Synthetic and structural studies of 1-halo-8-(alkylchalcogeno)naphthalene derivatives
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dc.contributor.author | Knight, Fergus Ross | |
dc.contributor.author | Fuller, Amy | |
dc.contributor.author | Buehl, Michael | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.contributor.author | Woollins, J Derek | |
dc.date.accessioned | 2016-01-15T15:40:07Z | |
dc.date.available | 2016-01-15T15:40:07Z | |
dc.date.issued | 2010-07-05 | |
dc.identifier | 4638426 | |
dc.identifier | cbd729cb-598f-4a5f-92be-417385c017d3 | |
dc.identifier | 000280216400030 | |
dc.identifier | 77954129828 | |
dc.identifier.citation | Knight , 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.201000435 | en |
dc.identifier.issn | 0947-6539 | |
dc.identifier.other | ORCID: /0000-0002-1095-7143/work/48131739 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861611 | |
dc.identifier.other | ORCID: /0000-0002-1498-9652/work/31779249 | |
dc.identifier.uri | https://hdl.handle.net/10023/8030 | |
dc.description | This work is funded by the EPSRC | en |
dc.description.abstract | A 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.extent | 12 | |
dc.format.extent | 745728 | |
dc.language.iso | eng | |
dc.relation.ispartof | Chemistry - A European Journal | en |
dc.subject | Chalcogens | en |
dc.subject | Density functional calculations | en |
dc.subject | Halogens | en |
dc.subject | Naphthalene | en |
dc.subject | peri-Substitution | en |
dc.subject | X-ray diffraction | en |
dc.subject | NMR chemical-shifts | en |
dc.subject | Pentacoordinate disilanes bearing | en |
dc.subject | Polyaromatic hydrocarbon ligands | en |
dc.subject | Naphthalene peri positions | en |
dc.subject | 4-center 6-electron bond | en |
dc.subject | Ray-diffraction data | en |
dc.subject | CENTER-DOT-P | en |
dc.subject | X-RAY | en |
dc.subject | Cation radicals | en |
dc.subject | Substituted naphthalenes | en |
dc.subject | QD Chemistry | en |
dc.subject.lcc | QD | en |
dc.title | Synthetic and structural studies of 1-halo-8-(alkylchalcogeno)naphthalene derivatives | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Office of the Principal | en |
dc.identifier.doi | 10.1002/chem.201000435 | |
dc.description.status | Peer reviewed | en |
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