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

Reference:

Clarke, C. S., Haynes, D. A., Smith, J. N. B., Batsanov, A. S., Howard, J. A. K., Pascu, S. I. and Rawson, J. M., 2010. The effect of fluorinated aryl substituents on the crystal structures of 1,2,3,5-dithiadiazolyl radicals. CrystEngComm, 12 (1), pp. 172-185.

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Official URL:

http://dx.doi.org/10.1039/b911636b

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.

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