Inter-molecular hydrogen bonding in N-methyl- N'-(pyridin-2-yl)benzene-1,2-di-amine

Gavin Collis; Alex Bilyk; Ueno Kazanori; Craig M Forsyth

doi:10.1107/S2056989022009173

Inter-molecular hydrogen bonding in N-methyl- N'-(pyridin-2-yl)benzene-1,2-di-amine

Acta Crystallogr E Crystallogr Commun. 2022 Sep 27;78(Pt 10):1048-1051. doi: 10.1107/S2056989022009173. eCollection 2022 Oct 1.

Authors

Gavin Collis¹, Alex Bilyk¹, Ueno Kazanori¹, Craig M Forsyth²

Affiliations

¹ CSIRO Manufacturing, Device and Engineering Systems Program, Private Bag 10, Melbourne, Victoria 3169, Australia.
² School of Chemistry, Monash University, Clayton, Victoria 3800, Australia.

Abstract

The structure of N-methyl-N'-(pyridin-2-yl)benzene-1,2-di-amine, C₁₂H₁₃N₃, at 123 K has ortho-rhom-bic (Pna2₁) symmetry. The title compound displays an unexpected proton-splitting pattern when studied by ¹H NMR spectroscopy. The X-ray crystallography analysis determined this to be caused by strong dual N-H⋯N hydrogen bonding.

Keywords: crystal structure; dimerization; heterocycles.; hydrogen bonding.

Grants and funding

Funding for this research was provided by: CSIRO Manufacturing Flexible Electronics Theme as part of the OLED research program.