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Journal Article

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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Seidel,  Rüdiger W.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Goddard,  Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Seidel, R. W., Goddard, R., Spiteller, M., & Kolev, T. M. (2015). The 1:1 Proton-Transfer Compounds of N,N- dimethyl-4-[(E )-2-(4-pyridinyl)vinyl]aniline with 3-Nitrophthalic and Perchloric acids. Journal of Chemical Crystallography, 45(2), 86-93. doi:10.1007/s10870-015-0569-z.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0027-B2B7-8
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.