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Updated: Jun 1, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Bis[eth-yl(2-hydroxy-ethyl)aza-nium] 2,2'-disulfanediyldibenzoate
Abstract:
The asymmetric unit of the title salt, 2C(4)H(12)NO(+)·C(14)H(8)O(4)S(2) (2-), contains an eth-yl(2-hydr-oxy)aminium cation and half a 2,2'-disulfanediyldibenzoate anion, with the latter disposed about a twofold axis. The cation is a straight chain with the exception of the terminal hydr-oxy group [the N-C-C-O torsion angle is 66.5 (2)°]. A twisted conformation is found for the anion [the C-S-S-C torsion angle is 91.51 (9)° and the dihedral angle between the rings is 81.01 (4)°]. A supra-molecular chain with base vector [101] and a tubular topology is formed in the crystal structure mediated by charge-assisted O-H⋯O(-) and N(+)-H⋯O(-) hydrogen bonding.
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The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...

