UCLA Chemists Create Unprecedented 3D Molecules Challenging Organic Chemistry Fundamentals

3D molecular structure with distorted carbon-carbon bonds, illustrating non-integer bond orders in a cage-shaped molecule.

For over a century, organic chemistry textbooks have declared certain molecular structures 'impossible'—until now. UCLA chemists led by Neil Garg have created cage-shaped molecules like cubene and quadricyclene, which defy traditional bonding rules by incorporating carbon-carbon double bonds in distorted three-dimensional geometries.

These molecules exhibit bond orders near 1.5, a deviation from the standard integer values (1, 2, or 3) taught in organic chemistry curricula.

Neil Garg said:

"Decades ago, chemists found strong support that we should be able to make alkene molecules like these, but because we're still very used to thinking about textbook rules of structure, bonding and reactivity in organic chemistry, molecules like cubene and quadricyclene have been avoided."

Ken Houk added:

"Neil's lab has figured out how to make these incredibly distorted molecules, and organic chemists are excited by what might be done with these unique structures."

The molecules are highly unstable and cannot be isolated, but their existence is supported by computational models and experimental evidence.

The research, funded by the National Institutes of Health, was published in Nature Chemistry. The study does not provide clinical guidance and represents early-phase research requiring further validation.

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