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Synthetic and structural studies of 1-halo-8-(alkylchalcogeno)naphthalene derivatives

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Date
05/07/2010
Author
Knight, Fergus Ross
Fuller, Amy
Buehl, Michael
Slawin, Alexandra Martha Zoya
Woollins, J Derek
Keywords
Chalcogens
Density functional calculations
Halogens
Naphthalene
peri-Substitution
X-ray diffraction
NMR chemical-shifts
Pentacoordinate disilanes bearing
Polyaromatic hydrocarbon ligands
Naphthalene peri positions
4-center 6-electron bond
Ray-diffraction data
CENTER-DOT-P
X-RAY
Cation radicals
Substituted naphthalenes
QD Chemistry
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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.
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
Publication
Chemistry - A European Journal
Status
Peer reviewed
DOI
https://doi.org/10.1002/chem.201000435
ISSN
0947-6539
Type
Journal article
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
Description
This work is funded by the EPSRC
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/8030

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