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Issue 1, 2010
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The effect of fluorinated aryl substituents on the crystal structures of 1,2,3,5-dithiadiazolyl radicals

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Abstract

The crystal structures of six new partially fluorinated aryl 1,2,3,5-dithiadiazolyls [ArCNSSN]˙ are reported [Ar = 2,6-F2C6H3 (4); Ar = 3,4-F2C6H3 (5); Ar = 3,5-F2C6H3 (6); Ar = 2,3,6-F3C6H2 (9); Ar = 2,4,6-F3C6H2 (11); and Ar = 3,4,5-F3C6H2 (12)] and compared with three previously reported structures in this series (Ar = 2,3-F2C6H3 (1); Ar = 2,5-F2C6H3 (3); Ar = 2,3,4-F3C6H2 (7)]. Radical 4 is shown to be polymorphic. Molecular electrostatic potential maps have been used to rationalise these structures. These reveal that whilst single F atoms appear to have little structure-directing influence, combinations of an ortho-F on the phenyl ring and a heterocyclic ring N, or several F atoms located in mutually ortho positions with respect to each other, generate significant regions of negative charge which have a substantial structure-directing influence.

Graphical abstract: The effect of fluorinated aryl substituents on the crystal structures of 1,2,3,5-dithiadiazolyl radicals

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Publication details

The article was received on 15 Jun 2009, accepted on 15 Sep 2009 and first published on 02 Oct 2009


Article type: Paper
DOI: 10.1039/B911636B
Citation: CrystEngComm, 2010,12, 172-185
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    The effect of fluorinated aryl substituents on the crystal structures of 1,2,3,5-dithiadiazolyl radicals

    C. S. Clarke, D. A. Haynes, J. N. B. Smith, A. S. Batsanov, J. A. K. Howard, S. I. Pascu and J. M. Rawson, CrystEngComm, 2010, 12, 172
    DOI: 10.1039/B911636B

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