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

Area of Science:

• Crystallography
• Organic Chemistry
• Spectroscopy

Background:

• The compound N-methyl-N'-(pyridin-2-yl)benzene-1,2-di-amine is a complex organic molecule.
• Understanding its structural and bonding properties is crucial for further chemical applications.

Purpose of the Study:

• To elucidate the crystal structure of N-methyl-N'-(pyridin-2-yl)benzene-1,2-di-amine at low temperature.
• To investigate the cause of an unusual proton-splitting pattern observed in its 1H NMR spectrum.

Main Methods:

• X-ray crystallography at 123 K.
• Proton Nuclear Magnetic Resonance (1H NMR) spectroscopy.

Main Results:

• The crystal structure was determined to be ortho-rhom-bic with Pna21 symmetry.
• A unique proton-splitting pattern in the 1H NMR spectrum was observed.
• Strong dual N-H⋯N hydrogen bonding was identified as the cause of the observed NMR splitting.

Conclusions:

• The crystal structure and hydrogen bonding network of N-methyl-N'-(pyridin-2-yl)benzene-1,2-di-amine were characterized.
• Dual N-H⋯N hydrogen bonds explain the unexpected proton-splitting in 1H NMR spectroscopy.
• This finding provides insights into the intermolecular interactions governing the compound's properties.