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Solid State Annular Tautomerism in a Molecule Containing Two Imidazole Moieties

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Abstract

The X-ray crystal structure of the 1:2 condensate (1) of hydrazine hydrate and 4-methyl-imidazole-5-carboxaldehyde has been determined. The molecule is centrosymmetric crystallising in the space group Fddd with cell dimensions: a = 10.557(14), b = 17.062(22), c = 24.759(27) Å. Fourier map shows that the NH hydrogen atom of each imidazole moiety has equal possibility of occupying any of its two ring N atoms. This poses the possibility of finding three tautomers in 1 in the solid state. Consideration of the H-bonding pattern observed in 1 and related B3LYP/6-311+G(2d,p) calculations show that only two tautomers are present in the solid state. The situation is compared with that in the structure of 4(5)-nitro-5(4)-methoxy-imidazole reported previously by Kubicki.

Graphical Abstract

The inherent disorder of the ring N–H hydrogen atoms in the shown centrosymmetric molecule (blue, C; deep blue, N; grey, H) which contains two imidazole moieties, poses the possibility of the coexistence of three tautomers in the solid state. The observed and theoretical [from B3LYP/6-311+G(2d,p) calculations] H-bonding pattern indicate that only two tautomers are present in the solid state.

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Acknowledgement

M. G. B. D. thanks EPSRC and the University of Reading for funds for the MARresearch Image Plate system.

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Authors and Affiliations

  1. School of Chemistry, University of Reading, Whiteknights, Reading, RG6 6AD, UK

    Michael G. B. Drew

  2. Department of Inorganic Chemistry, Indian Association for the Cultivation of Science, Calcutta, 700 032, India

    Debashree Das, Senjuti De, Jnan Prakash Naskar & Dipankar Datta

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  1. Michael G. B. Drew
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  2. Debashree Das
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  3. Senjuti De
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  4. Jnan Prakash Naskar
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  5. Dipankar Datta
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Correspondence to Dipankar Datta.

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Drew, M.G.B., Das, D., De, S. et al. Solid State Annular Tautomerism in a Molecule Containing Two Imidazole Moieties. J Chem Crystallogr 38, 507–512 (2008). https://doi.org/10.1007/s10870-008-9322-1

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  • DOI: https://doi.org/10.1007/s10870-008-9322-1

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