Abstract
1-t-Butyl-5-N-(dimethylaminomethylene)aminoimidazole-4-carbonyl cyanide (BUNDAMIC) is the first acyl cyanide to be synthesized from an imidazole-4-carboxylic acid, diethylphosphorocyanidate, and triethylamine and its structure determined by x-ray crystallography. It crystallizes with four molecules in the monoclinic space group C2/m with a = 17.824(2), b = 6.784(2), c = 11.039(2) Å, and β = 96.17(1)°; R = 0.036 over 1086 unique x-ray reflections. The cyanocarbonyl group is nearly linear, C-C≡ N angle 174.4(3)°, with dimensions C≡ N, 1.137(3); C-C 1.493(3); and C=O≡ N 1.224(3) Å. The imidazole ring, in the mirror plane, has a lengthened C4 = C5 bond of 1.421(3) A, and there is a short ring-closing approach, H⋯ O6 =2.07 Å, between the methyleneamino hydrogen and the carbonyl oxygen.
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Jones, D.W., Motevalli, M., Shaw, G. et al. The cyanocarbonyl group: synthesis and crystal structure of an imidazole carbonyl cyanide, C12N5OH17 . Journal of Chemical Crystallography 28, 561–564 (1998). https://doi.org/10.1023/A:1023200307429
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DOI: https://doi.org/10.1023/A:1023200307429