Structural Characterization of 4-Cyanoimidazolium-5-olate, 4,4-Diphenyl-5-imidazolinone, and 4,5-Dicyanoimidazole. A Novel Mesoionic Compound and Decoding of Intermolecular Hydrogen Bonds

Biphenyl- and phenylnaphthalenyl-substituted 1H-imidazole-4,5-dicarbonitrile catalysts for the coupling reaction of nucleoside methyl phosphonamidites

“…The bond lengths and angles in the 1H-imidazole-4,5dicarbonitrile groups of (I), (II) and (III) are in excellent agreement. They are also very similar to the corresponding bond lengths and angles observed in the crystal structure of 1H-imidazole-4,5-dicarbonitrile (Barni et al, 1997). The C-N bond lengths in the imidazole rings range from 1.325 (2) to 1.377 (2) Å , thus showing a considerable degree of delocalization of the double bonds in the ring.…”

5-Amino-1-benzyl-4-cyano-3-methylimidazolium toluene-p-sulfonate

“…The C4-C5 bond [1.3879 (19) Å ] shows reduced double bond character with respect to the corresponding bond distance [1.360 (14) Å ] found in imidazole residues (Allen et al, 1987). A similar distribution of bond distances has been found in other 4-cyanoimidazolium compounds (Barni et al, 1997). The pattern of N1-C7 and C7-C8 bonds [i.e.…”

Controlling the Interface between Salts, Solvates, Co-crystals, and Ionic Liquids with Non-stoichiometric Protic Azolium Azolates

“…The partial ionization is also observable by comparison of the bond distances in the [DCNIm] − anion and neutral HDCNim 21 (Cambridge Structural Database (CSD) ref code ZORTAB01, Figure 3d) where the double bonds C2N3 and C4C5 are slightly longer for the partially ionized azole than for the neutral compound, while the single C−N bonds are shorter in the anions. The bond distances are more consistent with our previously obtained system of [HC 1 im][DCNim], which exhibited fully ionized [DCNIm] − ions (CSD ref code DUXJOX).…”

“…Note that the disordered hydrogen atoms were omitted for clarity. (d) Comparison of the bond distances of the anions (based on OLEX2) in [HC 2 im]­[DCNim] with the structure of neutral HDCNim (ZORTAB01) . In addition, the fragments are compared to completely ionized [DCNim] − in [HC 1 im]­[DCNim] (DUXJOX) …”