《Planochromism of cyanoxime anions: Computational and mechanistic studies in solid state and solutions》 was published in Inorganica Chimica Acta in 2020. These research results belong to Morton, Jeffrey; Dennison, Richard; Nemykin, Victor; Gerasimchuk, Nikolay. Application In Synthesis of 3-Oxo-3-phenylpropanenitrile The article mentions the following:
The benzoylcyanoxime, NC-C(=N-OH)-C(O)-C6H5 (later H(BCO)), represents a new ampolydentate ligand that received attention in the light of useful biol. properties of its coordination compounds Colorless H(BCO), upon deprotonation, gains color that depends on the counter-cation and the system in general. Five derivatives of H(BCO), with colorless organic and inorganic mono-cations – Cs, Tl, Ag, N(CH3)4 and As(C6H5)4 – were synthesized and characterized by the X-ray anal., vibrational and electronic spectroscopy. Compounds exhibited unexpected and significant differences in color, both in solid state and in solutions, that were challenging to explain, thereby warranting detailed investigation including high-level DFT/TDFT computations. It was found that the BCO- anion demonstrates neg. solvatochromic in polar protic ROH (R=H, CH3, C2H5, C3H7, C4H9) solvents, and appears yellow in color, as tetraalkylammonium or alkali metal salts. In polar aprotic solvents, such as CH3CN, DMF, and DMSO, solutions of the BCO- anion are red. The color originates from n → π * transition in the anion. Solid state structures evidenced a considerable dependence on planarity of the BCO- anion on its color, as well as on the character of bonding in the C-N-O fragment: yellow color is associated with an oxime (bond length C-N is shorter than N-O), while red color is due to the nitroso character (bond length C-N is longer than the N-O). An addition of ethanol to red solutions of the BCO-containing salts leads to the color change to yellow, which is the result of the formation of an H-bond between the C-N-O fragment of cyanoxime and the solvent, also leading to the flattening of the structure. An explanation for this new color-changing effect was offered, based on exptl. evidence and TD/DFT calculations In the experiment, the researchers used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Application In Synthesis of 3-Oxo-3-phenylpropanenitrile)
3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.Application In Synthesis of 3-Oxo-3-phenylpropanenitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts