2,6-Bis(diazaboryl)pyridine: A Superbasic Sterically Demanding Pyridine Ligand

Area of Science:

• Organic Chemistry
• Coordination Chemistry
• Supramolecular Chemistry

Background:

• Pyridine derivatives are crucial in various chemical applications.
• Developing superbasic compounds with tunable properties is an ongoing challenge.
• Proton sponges are known for their high basicity but can have steric limitations.

Purpose of the Study:

• To synthesize a sterically demanding superbasic pyridine.
• To investigate the effect of boryl groups on pyridine basicity.
• To explore the utility of this pyridine as an N-donor ligand.

Main Methods:

• A convenient one-pot synthesis route was employed.
• Density Functional Theory (DFT) calculations were used to determine gas phase basicity.
• Coordination chemistry studies involving Lewis adducts with haloboranes were performed.

Main Results:

• The functionalized pyridine achieved a calculated gas phase basicity of 1012 kJ/mol, exceeding that of 1,8-bis(dimethylamino)naphthalene.
• The boryl groups were oriented orthogonally, not hindering the N-position.
• The pyridine successfully acted as a neutral N-donor ligand, forming Lewis adducts with haloboranes.

Conclusions:

• A novel superbasic pyridine with enhanced basicity has been synthesized.
• This pyridine offers a promising alternative to existing ligands in coordination chemistry.
• Its unique structure allows for tunable coordination properties and potential for new ligand design.