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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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Abstract

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.

Item type: Article
ID code: 1121
Keywords: three fluoro-substituted acetoacetanilides, C10H10FNO2, planar structure, intramolecular hydrogen bonding, aromatic ring, fluorine, steric, electronegativity, Chemistry
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Faculty of Humanities and Social Sciences (HaSS) > School of Education > Education
Related URLs:
    Depositing user: Catriona Mccallum
    Date Deposited: 22 May 2006
    Last modified: 12 Mar 2012 10:36
    URI: http://strathprints.strath.ac.uk/id/eprint/1121

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