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Updated: Jun 5, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Dibenzo-18-crown-6-picric acid-water (1/2/3)
Abstract:
In the crown ether ring of the title compound, C(20)H(24)O(6)·2C(6)H(3)N(3)O(7)·3H(2)O, the O-C(H(2))-C(H(2))-O torsion angles indicate a gauche conformation of the ethyl-eneoxy units, while the C-O-C-C torsion angles indicate planarity of these segments; the dihedral angle between the two benzene rings is 44.53 (13)°. In both picric acid mol-ecules, one of the nitro groups is twisted away from the attached ring. The mol-ecules are linked into chains along the b axis via inter-molecular O-H⋯O hydrogen bonds. In addition, the crystal structure is stabilized by C-H⋯O hydrogen bonds and π-π inter-actions [centroid-centroid distance between benzene rings = 3.5697 (16) Å].
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The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

