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Journal of Chemical Crystallography

, Volume 45, Issue 2, pp 86–93 | Cite as

The 1:1 Proton-Transfer Compounds of N,N -dimethyl-4-[(E)-2-(4-pyridinyl)vinyl]aniline with 3-Nitrophthalic and Perchloric acids

  • Rüdiger W. SeidelEmail author
  • Richard Goddard
  • Michael Spiteller
  • Tsonko M. Kolev
Original Paper

Abstract

The crystal structures of the 1:1 proton-transfer compounds of the dipolar donor-π-acceptor compound N,N-dimethyl-4-[(E)-2-(4-pyridinyl)vinyl]aniline (1), also named dimethylamino-stilbazole, with 3-nitrophthalic and perchloric acids, viz. (E)-4-[4-(dimethylamino)styryl]pyridinium 2-carboxy-3-nitrobenzoate monohydrate (2) and (E)-4-[4-(dimethylamino)styryl]pyridinium perchlorate (3) are described. A redetermination of the structure of the parent free base 1 at 100 K is also reported. The (E)-4-[4-(dimethylamino)styryl]pyridinium ion exhibits slight whole molecule disorder in 2 and 3. Compound 2 is the first organic salt that contains the unusual monoanion of 3-nitrophthalic acid that is deprotonated at the 1-carboxyl group.

Graphical Abstract

The crystal structures of the 1:1 proton-transfer compounds of the dipolar donor-π-acceptor compound N,N-dimethyl-4-[(E)-2-(4-pyridinyl)vinyl]aniline with 3-nitrophthalic and perchloric acids, viz. (E)-4-[4-(dimethylamino)styryl]pyridinium 2-carboxy-3-nitrobenzoate monohydrate and (E)-4-[4-(dimethylamino)styryl]pyridinium perchlorate are described.

Keywords

Chromophoric materials Pyridinium salts Proton-transfer Crystal structure 

Notes

Acknowledgements

T. M. K. would like to thank the Alexander von Humboldt Foundation. R. W. S. is thankful to Professor Christian W. Lehmann for his support of this project.

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Rüdiger W. Seidel
    • 1
    Email author
  • Richard Goddard
    • 1
  • Michael Spiteller
    • 2
  • Tsonko M. Kolev
    • 3
  1. 1.Max-Planck-Institut für KohlenforschungMülheimGermany
  2. 2.Institut für UmweltforschungTechnische Universität DortmundDortmundGermany
  3. 3.Institute of Molecular Biology “Roumen Tsanev”, Bulgarian Academy of SciencesSofiaBulgaria

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