Three negative charges crammed onto carbons in a single molecule

The first organic compound with three negative charges centred on carbon atoms has been synthesised by German researchers.

Carbon atoms aren’t great at stabilising negative charges. Compounds in which carbon has a anion-like character, like tert-butyl lithium, are often very reactive as the carbon desperately wants to share its surplus electron density. Molecules with several carbanions usually need help from electron-withdrawing groups or metals to stabilise their negative charges to prevent them rapidly falling apart.