Formation of H-bonded ionic associates in reactions of 5-nitrosalicylaldehyde with secondary amines

L. Yu Ukhin, Rostov State University
G. I. Orlova, Rostov State University
Sergey Lindeman, Marquette University
V, N, Khrustalev, Russian Academy of Sciences
Yu T. Struchkov, Russian Academy of Sciences

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.