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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.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 | PURE: 4638426 | |
dc.identifier.other | PURE UUID: cbd729cb-598f-4a5f-92be-417385c017d3 | |
dc.identifier.other | WOS: 000280216400030 | |
dc.identifier.other | Scopus: 77954129828 | |
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.language.iso | eng | |
dc.relation.ispartof | Chemistry - A European Journal | en |
dc.rights | Copyright © 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.201000435 | 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.description.version | Postprint | 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 | https://doi.org/10.1002/chem.201000435 | |
dc.description.status | Peer reviewed | en |
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