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Updated: Apr 30, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
(Meth-oxy-methyl-idene)di-methyl-aza-nium tetra-phenyl-borate aceto-nitrile monosolvate
Ioannis Tiritiris1, Stefan Saur1, Willi Kantlehner1
1Fakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstrasse 1, D-73430 Aalen, Germany.
Abstract:
In the cation of the title salt, C4H10NO(+)·C24H20B(-)·C2H3N, the C-N bond lengths are 1.2864 (16), 1.4651 (17) and 1.4686 (16) Å, indicating double- and single-bond character, respectively. The C-O bond length of 1.2978 (15) Å shows double-bond character, pointing towards charge delocalization within the NCO plane of the iminium ion. C-H⋯π inter-actions are present between the methine H atom and two of the phenyl rings of the tetra-phenyl-borate ion. The latter forms an aromatic pocket in which the cation is embedded. The iminium ion is further connected through a C-H⋯N hydrogen bond to the aceto-nitrile mol-ecule. This leads to the formation of a two-dimensional supramolecular pattern along the bc plane.
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The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.

