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Open Access research which pushes advances in bionanotechnology

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SIPBS is a major research centre in Scotland focusing on 'new medicines', 'better medicines' and 'better use of medicines'. This includes the exploration of nanoparticles and nanomedicines within the wider research agenda of bionanotechnology, in which the tools of nanotechnology are applied to solve biological problems. At SIPBS multidisciplinary approaches are also pursued to improve bioscience understanding of novel therapeutic targets with the aim of developing therapeutic interventions and the investigation, development and manufacture of drug substances and products.

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Structural motifs in acetoacetanilides: the effect of a fluorine substituent

Chisholm, G. and Kennedy, A.R. and Beaton, L. and Brook, E. (2002) Structural motifs in acetoacetanilides: the effect of a fluorine substituent. Acta Crystallographica Section C: Crystal Structure Communications, 58 (11). o645-o648. ISSN 0108-2701

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The structures of three fluoro-substituted acetoacetanilides, namely 2'-, 3'- and 4'-fluoro­acetoacetanilide, all C10H10FNO2, are presented and discussed. We observe a planar structure with intramolecular hydrogen bonding when the F atom is in the ortho position of the aromatic ring, and a twisted structure with intermolecular hydrogen bonding when the F atom is in the meta or para positions. It can be predicted which of these two structural motifs will be adopted by considering the position of any aromatic substituents. In this regard, fluorine appears to mimic the steric effect of a larger substituent, which we attribute to its high electronegativity.