Formation of H-bonded ionic associates in reactions of 5-nitrosalicylaldehyde with secondary amines
Russian Chemical Bulletin, Vol. 44, No. 5 (May 1995): 913-916. DOI.
Sergey Lindeman was affiliated with A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russian Federation at the time of publication.
5-Nitrosalicylaldehyde reacts with highly basic secondary aliphatic amines to form molecular complexes of 1 ∶ 1 composition. The complexes with piperidine, diethylamine, dipentylamine, and dibenzylamine (1–4, respectively) have been obtained in the crystalline state and characterized. The X-ray diffraction structural analysis of complex1 demonstrated that it exists in a crystal as an H-bonded dimeric ionic associate [C5H12N+ · C7H4NO 4 − ]2 formed as a result of the transfer of the phenyl proton of the aldehyde to the piperidine N atom. According to the results of IR spectroscopy, the other complexes obtained have similar structures.