Does cation break the cyano bond? A critical evaluation of nitrile-cation interaction.

DFT and G4 results reveal that cations display the following trends in imparting its positive charge to acrylonitrile; H⁺ > Li⁺ > Na⁺ > K⁺ for group I and Be²⁺ > Mg²⁺ > Ca²⁺ for group II. Solvation by water molecules and interaction with cation make the cyano bond more polarized and exhibits ketene-imine character. Bond order in nitrile-cation complexes has been predicted based on the s character of the covalent bond orbitals.

2-(2-Naphth-yloxy)pyrimidine.

In the title compound, C(14)H(10)N(2)O, the organic rings are inclined at an angle of 86.1 (1)°. The angle at the ether O atom is widened to 117.

4-Chloro-N-(pyrimidin-2-yl)aniline.

The two aromatic rings in the title compound, C(10)H(8)ClN(3), open the angle at the planar N atom to 128.00 (12)°. The amino N atom of one mol-ecule forms a hydrogen bond to the 1-N atom of an adjacent pyrimidyl ring, generating a hydrogen-bonded dimer.