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The X-ray Structure of N-(Acetylamino)phthalimide, an Atypical Triacylhydrazine

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Abstract

N-(Acetylamino)phthalimide [monoclinic, a = 7.0228(15), b = 4.7285(8), c = 28.882(6) Å, β = 90.131(7)°, space group P21/c] shows an unusual crystal structure with marked pyramidalization at the phthalimide N and strong intermolecular NH to CO hydrogen bonding leading to the groups at the two ends of the hydrazine adopting an almost perpendicular arrangement. A survey of previous triacyl and tetraacyl hydrazine structures shows that both these features are unusual, with most examples being essentially planar at N and with torsion angles about the N–N bond of 63°–82°.

Graphical Abstract

N-Acetylaminophthalimide adopts a structure with a pyramidalized imide nitrogen and groups at either end of the N–N bond almost perpendicular to accommodate formation of intermolecular hydrogen-bonded stacks.

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Authors and Affiliations

  1. School of Chemistry, University of St Andrews, St Andrews, Fife, KY16 9ST, UK

    Kati M. Aitken, R. Alan Aitken & Alexandra M. Z. Slawin

Authors
  1. Kati M. Aitken
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  2. R. Alan Aitken
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  3. Alexandra M. Z. Slawin
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Correspondence to R. Alan Aitken.

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Aitken, K.M., Aitken, R.A. & Slawin, A.M.Z. The X-ray Structure of N-(Acetylamino)phthalimide, an Atypical Triacylhydrazine. J Chem Crystallogr 44, 25–29 (2014). https://doi.org/10.1007/s10870-013-0478-y

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  • DOI: https://doi.org/10.1007/s10870-013-0478-y

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