(Nanowerk News) An unusual molecule once thought to be too strained to exist has been transformed into another contorted compound by RIKEN chemists, testing the limits of how far carbon-based molecules can be distorted by combining them with metal atoms.
The complexity of organic chemistry is largely due to the tendency of carbon atoms to join together into chains and rings. Yet carbon–carbon triple bonds (-C=C-, also known as alkynes) are relatively rare in ring systems, because they prefer to connect to other atoms in straight lines.
It’s just about possible to bend this alkyne group so that it will fit into a ring of seven carbon atoms. But smaller rings are extremely reactive, due to the strain put on that triple bond, explains Noriyuki Suzuki of RIKEN’s Advanced Science Institute in Wako. “It was believed that it was impossible to isolate them in a pure form,” he says.
The researchers are now exploring how this molecule behaves. Recently, they have used it to create another ring system containing two carbon–carbon double bonds sitting side by side (-C=C=C-), also known as an allene. Under normal circumstances a five-membered ring containing an allene would be too strained to exist for long—but with the zirconium atom in place, the team found that the cycloallene compound could be isolated.
Pushing back the boundaries of chemistry. This molecular structure shows a zirconium atom (green) sitting in a ring with four other carbon atoms (purple) in the new cycloallene compound. In the background, the chemical reaction shows the interconversion between alkyne and allene. (Image: RIKEN)