Title of article :
Synthesis and comparative structural study of 2-(pyridin-2-yl)-1H-perimidine and its mono- and di-N-methylated analogues
Author/Authors :
Kalle, Paulina Department of Chemistry - Lomonosov Moscow State University, Russian Federation , Tatarin, Sergei V. Department of Chemistry - Lomonosov Moscow State University, Russian Federation , Zakharov, Alexander Yu. N.S. Kurnakov Institute of General and Inorganic Chemistry - Russian Academy of Sciences, Russian Federation , Kiseleva, Marina A. Department of Chemistry - Lomonosov Moscow State University, Russian Federation , Bezzubov, Stanislav I. N.S. Kurnakov Institute of General and Inorganic Chemistry - Russian Academy of Sciences, Russian Federation
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 1–3, the molecular entities all are assembled through π–π and C—H⋯π interactions.
Keywords :
crystal structure , perimidine , π–π stacking , π–π stacking , hydrogen-bonding , NMR study
Journal title :
Acta Crystallographica Section E: Crystallographic Communications
