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

Acta Crystallographica Section E: Crystallographic Communications

Marina A. Kiseleva¹  Sergei V. Tatarin¹  Paulina Kalle¹  Stanislav I. Bezzubov²  Alexander Yu. Zakharov² 

[1] Department of Chemistry, Lomonosov Moscow State University, Lenin's Hills, 1-3, Moscow, 119991, Russian Federation;N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky pr. 31, Moscow 119991, Russian Federation;

关键词: crystal structure;    perimidine;    π–π stacking;    hydrogen-bonding;    nmr study;   

DOI  :  10.1107/S205698902100013X

来源: DOAJ

【 摘 要 】

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 1–3, the molecular entities all are assembled through π–π and C—H...π interactions.

【 授权许可】

Unknown