NDLI: Onset of three-centre, four-electron bonding in peri-substituted acenaphthenes : A structural and computational investigation

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Onset of three-centre, four-electron bonding in peri-substituted acenaphthenes : A structural and computational investigation

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Onset of three-centre, four-electron bonding in peri-substituted acenaphthenes : A structural and computational investigation

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Aschenbach, Lara K. Bühl, Michael Woollins, J. Derek Randall, Rebecca A. M. Baggott, Alex Knight, Fergus R. Cordes, David B. Slawin, Alexandra M. Z.
Description	Author Affiliation: Aschenbach LK ( School of Chemistry, University of St Andrews, St Andrews, Fife, UK.)
Abstract	Two series of sterically crowded peri-substituted acenaphthenes have been prepared, containing mixed halogen - chalcogen functionalities at the 5,6-positions in A1–A6 (Acenap[X][EPh] (Acenap = acenaphthene-5,6-diyl; X = Br, I; E = S, Se, Te) and chalcogen -chalcogen moieties in A7–A12 (Acenap[EPh][E′Ph] (Acenap = acenaphthene-5,6-diyl; E/E′ = S, Se, Te). The related dihalide compounds A13–A16 Acenap[XX′] (XX′ = BrBr, II, IBr, ClCl) have also been prepared. Distortion of the acenaphthene framework away from the ideal was studied as a function of the steric bulk of the interacting halogen and chalcogen atoms occupying the peri-positions. The acenaphthene series experiences a general increase in peri-separation for molecules accommodating heavier congeners and maps the trends observed previously for the analogous naphthalene compounds N1–N12 (Nap[X][EPh], Nap[EPh][E′Ph] (X = Br, I; E/E′ = S, Se, Te). The conformation of the aromatic ring systems and subsequent location of p-type lone-pairs dominates the geometry of the peri-region. The differences in peri-separations observed for compounds adopting differing conformations of the peri-substituted phenyl group can be correlated to the ability of the frontier orbitals of the halogen or chalcogen atoms to take part in attractive or repulsive interactions. Density-functional studies have confirmed these interactions and suggested the onset of formation of three-centre, four-electron bonding under appropriate geometric conditions.
ISSN	14779226
Issue Number	11
Journal	Dalton Trans.
Volume Number	41
e-ISSN	13645447
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2012-03-21
Publisher Place	Great Britain (UK)
Access Restriction	Subscribed
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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