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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.

Details

Item Type Articles
CreatorsClarke, C. S., Haynes, D. A., Smith, J. N. B., Batsanov, A. S., Howard, J. A. K., Pascu, S. I. and Rawson, J. M.
DOI10.1039/b911636b
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code27160

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