The role of functional nitro and cyano groups in the self-assembly of 1,3-dithiole-2-thione-halogen adducts

Peter Skabara, Alexander Kanibolotsky, Simon Render, Rory Berridge, David J. Crouch, Neil Bricklebank, Simon J. Coles, Thomas Gelbrich, M. B. Hursthouse

Research output: Contribution to journal › Article

6 Citations (Scopus)

Abstract

The synthesis of five new dihalogen/interhalogen charge transfer adducts featuring cyano and nitro functionalized 1,3-dithiole-2-thiones have been prepared and characterized by x-ray crystallography. The structures feature a complex series of intermolecular close contacts between heteroatoms, as well as hydrogen bonding, to give highly ordered, polymeric assemblies. The adduct 4.IBr crystallizes in a noncentrosymmetric chiral space group and features a stack of molecules assembled through hydrogen bonds. The functional groups of all adducts participate in networks of close contacts, but do not affect the coordination environment of the dihalogen/interhalogen species.
LanguageUndefined/Unknown
Pages176-184
Number of pages9
JournalHeteroatom Chemistry
Volume18
Issue number2
DOIs
Publication statusPublished - 2007

Keywords

  • cyano groups
  • nitro groups
  • halogen adducts
  • crystallography

Cite this

Skabara, P., Kanibolotsky, A., Render, S., Berridge, R., Crouch, D. J., Bricklebank, N., ... Hursthouse, M. B. (2007). The role of functional nitro and cyano groups in the self-assembly of 1,3-dithiole-2-thione-halogen adducts. Heteroatom Chemistry, 18(2), 176-184. https://doi.org/10.1002/hc.20327
Skabara, Peter ; Kanibolotsky, Alexander ; Render, Simon ; Berridge, Rory ; Crouch, David J. ; Bricklebank, Neil ; Coles, Simon J. ; Gelbrich, Thomas ; Hursthouse, M. B. / The role of functional nitro and cyano groups in the self-assembly of 1,3-dithiole-2-thione-halogen adducts. In: Heteroatom Chemistry. 2007 ; Vol. 18, No. 2. pp. 176-184.
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abstract = "The synthesis of five new dihalogen/interhalogen charge transfer adducts featuring cyano and nitro functionalized 1,3-dithiole-2-thiones have been prepared and characterized by x-ray crystallography. The structures feature a complex series of intermolecular close contacts between heteroatoms, as well as hydrogen bonding, to give highly ordered, polymeric assemblies. The adduct 4.IBr crystallizes in a noncentrosymmetric chiral space group and features a stack of molecules assembled through hydrogen bonds. The functional groups of all adducts participate in networks of close contacts, but do not affect the coordination environment of the dihalogen/interhalogen species.",
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Skabara, P, Kanibolotsky, A, Render, S, Berridge, R, Crouch, DJ, Bricklebank, N, Coles, SJ, Gelbrich, T & Hursthouse, MB 2007, 'The role of functional nitro and cyano groups in the self-assembly of 1,3-dithiole-2-thione-halogen adducts' Heteroatom Chemistry, vol. 18, no. 2, pp. 176-184. https://doi.org/10.1002/hc.20327

The role of functional nitro and cyano groups in the self-assembly of 1,3-dithiole-2-thione-halogen adducts. / Skabara, Peter; Kanibolotsky, Alexander; Render, Simon; Berridge, Rory; Crouch, David J.; Bricklebank, Neil; Coles, Simon J.; Gelbrich, Thomas; Hursthouse, M. B.

In: Heteroatom Chemistry, Vol. 18, No. 2, 2007, p. 176-184.

Research output: Contribution to journal › Article

TY - JOUR

T1 - The role of functional nitro and cyano groups in the self-assembly of 1,3-dithiole-2-thione-halogen adducts

AU - Skabara, Peter

AU - Kanibolotsky, Alexander

AU - Render, Simon

AU - Berridge, Rory

AU - Crouch, David J.

AU - Bricklebank, Neil

AU - Coles, Simon J.

AU - Gelbrich, Thomas

AU - Hursthouse, M. B.

PY - 2007

Y1 - 2007

N2 - The synthesis of five new dihalogen/interhalogen charge transfer adducts featuring cyano and nitro functionalized 1,3-dithiole-2-thiones have been prepared and characterized by x-ray crystallography. The structures feature a complex series of intermolecular close contacts between heteroatoms, as well as hydrogen bonding, to give highly ordered, polymeric assemblies. The adduct 4.IBr crystallizes in a noncentrosymmetric chiral space group and features a stack of molecules assembled through hydrogen bonds. The functional groups of all adducts participate in networks of close contacts, but do not affect the coordination environment of the dihalogen/interhalogen species.

AB - The synthesis of five new dihalogen/interhalogen charge transfer adducts featuring cyano and nitro functionalized 1,3-dithiole-2-thiones have been prepared and characterized by x-ray crystallography. The structures feature a complex series of intermolecular close contacts between heteroatoms, as well as hydrogen bonding, to give highly ordered, polymeric assemblies. The adduct 4.IBr crystallizes in a noncentrosymmetric chiral space group and features a stack of molecules assembled through hydrogen bonds. The functional groups of all adducts participate in networks of close contacts, but do not affect the coordination environment of the dihalogen/interhalogen species.

KW - cyano groups

KW - nitro groups

KW - halogen adducts

KW - crystallography

U2 - 10.1002/hc.20327

DO - 10.1002/hc.20327

M3 - Article

VL - 18

SP - 176

EP - 184

JO - Heteroatom Chemistry

T2 - Heteroatom Chemistry

JF - Heteroatom Chemistry

SN - 1042-7163

IS - 2

ER -

Skabara P, Kanibolotsky A, Render S, Berridge R, Crouch DJ, Bricklebank N et al. The role of functional nitro and cyano groups in the self-assembly of 1,3-dithiole-2-thione-halogen adducts. Heteroatom Chemistry. 2007;18(2):176-184. https://doi.org/10.1002/hc.20327

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