Synthesis and comparative structural study of 2-(pyridin-2-yl)-1H-perimidine and its mono- and di-N-methylated analogues

Author:

Kalle Paulina,Tatarin Sergei V.,Zakharov Alexander Yu.,Kiseleva Marina A.,Bezzubov Stanislav I.ORCID

Abstract

The title compounds, 2-(pyridin-2-yl)-1H-perimidine (C16H11N3; 1), 1-methyl-2-(pyridin-2-yl)-1H-perimidine (C17H13N3; 2), and 1,3-dimethyl-2-(pyridin-2-yl)-1H-perimidinium iodide (C18H16N3 +·I; 3) were synthesized under mild conditions and their structures were determined by 1H NMR spectroscopy and single-crystal X-ray analysis. The N-methylation of the nitrogen atom(s) at the perimidine moiety results in a significant increase of the interplane angle between the pyridin-2-yl ring and the perimidine system. The unsubstituted perimidine (1) forms a weak intramolecular N—H...N bond that consolidates the molecular conformation. In the crystal structures of 13, the molecular entities all are assembled through π–π and C—H...π interactions.

Funder

Presidential Grant Program

Publisher

International Union of Crystallography (IUCr)

Subject

Condensed Matter Physics,General Materials Science,General Chemistry

Reference14 articles.

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