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

Fergus Ross Knight, Amy Fuller, Michael Buehl, Alexandra Martha Zoya Slawin, J Derek Woollins

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22 Citations (Scopus)


A series of eight 1-halo-8-(alkylchalcogeno)naphthalene derivatives (18; 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 58 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 58 revealed Wiberg bond index values of 0.05–0.08, which indicate minor interactions taking place between the non-bonded atoms in these compounds.
Original languageEnglish
Pages (from-to)7605-7616
Number of pages12
JournalChemistry - A European Journal
Issue number25
Publication statusPublished - 5 Jul 2010


  • 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
  • X-RAY
  • Cation radicals
  • Substituted naphthalenes


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