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

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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.

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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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Authors and Affiliations

  1. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim, Germany

    Rüdiger W. Seidel & Richard Goddard

  2. Institut für Umweltforschung, Technische Universität Dortmund, Otto-Hahn-Straße 6, 44227, Dortmund, Germany

    Michael Spiteller

  3. Institute of Molecular Biology “Roumen Tsanev”, Bulgarian Academy of Sciences, Acad. G. Bonchev Str. 21, 1113, Sofia, Bulgaria

    Tsonko M. Kolev

Authors
  1. Rüdiger W. Seidel
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  2. Richard Goddard
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  4. Tsonko M. Kolev
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Correspondence to Rüdiger W. Seidel.

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Seidel, R.W., Goddard, R., Spiteller, M. et al. The 1:1 Proton-Transfer Compounds of N,N -dimethyl-4-[(E)-2-(4-pyridinyl)vinyl]aniline with 3-Nitrophthalic and Perchloric acids. J Chem Crystallogr 45, 86–93 (2015). https://doi.org/10.1007/s10870-015-0569-z

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  • DOI: https://doi.org/10.1007/s10870-015-0569-z

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