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

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-methyl-ation of the nitro-gen atom(s) at the perimidine moiety results in a significant increase of the inter-plane angle between the pyridin-2-yl ring and the perimidine system. The unsubstituted perimidine (1) forms a weak intra-molecular N-H⋯N bond that consolidates the mol-ecular conformation. In the crystal structures of 1-3, the mol-ecular entities all are assembled through π-π and C-H⋯π inter-actions.

SUBMITTER: Kalle P 

PROVIDER: S-EPMC7869552 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Synthesis and comparative structural study of 2-(pyridin-2-yl)-1<i>H</i>-perimidine and its mono- and di-<i>N</i>-methyl-ated analogues.

Kalle Paulina P   Tatarin Sergei V SV   Zakharov Alexander Yu AY   Kiseleva Marina A MA   Bezzubov Stanislav I SI  

Acta crystallographica. Section E, Crystallographic communications 20210108 Pt 2

The title compounds, 2-(pyridin-2-yl)-1<i>H</i>-perimidine (C<sub>16</sub>H<sub>11</sub>N<sub>3</sub>; <b>1</b>), 1-methyl-2-(pyridin-2-yl)-1<i>H</i>-perimidine (C<sub>17</sub>H<sub>13</sub>N<sub>3</sub>; <b>2</b>), and 1,3-dimethyl-2-(pyridin-2-yl)-1<i>H</i>-perimidinium iodide (C<sub>18</sub>H<sub>16</sub>N<sub>3</sub> <sup>+</sup>·I<sup>-</sup>; <b>3</b>) were synthesized under mild conditions and their structures were determined by <sup>1</sup>H NMR spectroscopy and single-crystal X-ray anal  ...[more]

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