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Molecular and crystal structure of 1-amino-X-pyrazinium mesitylenesulfonates

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Abstract

X-Ray diffraction analysis was performed of 1-amino-X-pyrazinium mesitylenesulfonates (X=H, 2-NH2, 3-NHCOMe, 3-OMe, 3-Cl). In all events save 1,2-diaminopyrazinium cation the bond length of N-NH2 was shorter than that of N-N bond but considerably longer than the length of the double bond N=N. In the 1,2-diaminopyrazinium cation the bond distance C2-NH2 was close to the length of a common double bond C=N indicating the iminium character of the cation. Quantum-chemical calculations [AM1, PM3, DFT/(PBE/3z), B3LYP/6-31G++(2d,p)] provided the geometry of cations similar to the experimental one. In the crystals under investigation motifs were observed of 0D, 1D, and 2D type mainly due to hydrogen bonds N-H···O and π-stacking interactions of the aromatic rings.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, Novosibirsk, 630090, Russia

    R. V. Andreev, G. I. Borodkin, A. Yu. Vorob’ev, Yu. V. Gatilov & V. G. Shubin

  2. Novosibirsk State University, Novosibirsk, Russia

    G. I. Borodkin & A. Yu. Vorob’ev

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  1. R. V. Andreev
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  2. G. I. Borodkin
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  3. A. Yu. Vorob’ev
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  4. Yu. V. Gatilov
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  5. V. G. Shubin
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Correspondence to G. I. Borodkin.

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Original Russian Text © R.V. Andreev, G.I. Borodkin, A.Yu. Vorob’ev, Yu.V. Gatilov, V.G. Shubin, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 2, pp. 296–304.

For preliminary communication see [1].

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Andreev, R.V., Borodkin, G.I., Vorob’ev, A.Y. et al. Molecular and crystal structure of 1-amino-X-pyrazinium mesitylenesulfonates. Russ J Org Chem 44, 292–301 (2008). https://doi.org/10.1134/S1070428008020188

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