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Researchers reported two different quantum-tunnelling reactions occurring at the same time in separate conformers of one molecule. In nitrogen matrices at 10 and 20 kelvin, syn and anti forms of triplet 2-formyl-3-fluorophenylnitrene each rearranged into a different product: the syn form by heavy-atom tunnelling, the anti form by hydrogen-atom tunnelling.
What did the researchers discover?
The 2022 study examined triplet 2-formyl-3-fluorophenylnitrene, produced by ultraviolet irradiation of 2-formyl-3-fluorophenyl azide. The researchers trapped the molecules in solid nitrogen and followed their products and reaction kinetics with infrared spectroscopy.
The key finding was that the molecule’s two conformers took distinct pathways at the same time. A conformer is one of the different spatial arrangements a molecule can adopt without changing which atoms it contains. Here, the syn conformer formed 2,1-benzisoxazole, while the anti conformer formed imino-ketene.
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| Starting conformer | Assigned tunnelling pathway | Product | Reported rate and half-life |
|---|---|---|---|
| syn | Heavy-atom tunnelling | 2,1-benzisoxazole | Approximately 1 × 10−3 s−1; approximately 11 minutes |
| anti | Hydrogen-atom tunnelling | imino-ketene | Approximately 6 × 10−3 s−1; approximately 2 minutes |
The rate constants and half-lives are the paper’s reported values for this matrix-isolated system, not general rates for quantum tunnelling reactions. The authors measured the kinetics at 10 and 20 K.
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Why is simultaneous tunnelling unusual?
In a conventional reaction picture, molecules cross an energy barrier by reaching a transition state. Quantum tunnelling offers another route: a particle can pass through a barrier rather than going over it. Tunnelling is familiar for light particles such as hydrogen, but the study assigned the syn pathway to tunnelling involving heavier atoms—an unusual feature of this reaction.
More strikingly, the two conformers did not first interconvert and then yield a common product distribution. The researchers observed each conformer proceeding along its own tunnelling pathway. Although computations indicated an interconversion barrier lower than the barriers for the observed rearrangements, no conformer interconversion was observed. The measured rates were temperature-independent across the reported 10 K and 20 K measurements, and computations supported the proposed pathways.
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The authors argued that the product outcome in this system is not accounted for by the conventional kinetic-control or thermodynamic-control explanations they considered. Peter Schreiner, commenting on the result in Chemistry World, said: “The reaction outcome cannot be understood on the commonly accepted grounds of kinetic versus thermodynamic control. Only tunnelling control can help rationalise the observations made.”
What does this result mean—and what does it not show?
It demonstrates an unusual reaction-control mechanism in a highly specialized experiment: a specific nitrene, isolated in solid nitrogen at cryogenic temperatures, followed by infrared spectroscopy. It does not establish that ordinary synthetic reactions generally tunnel, nor does it demonstrate a practical synthesis under everyday laboratory conditions.
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The researchers have discussed investigating reactions under conditions closer to conventional laboratory chemistry, including liquid-phase and higher-temperature settings. Those are prospective research directions, not results established by this experiment. The primary report is Cláudio M. Nunes and colleagues’ “Simultaneous Tunneling Control in Conformer-Specific Reactions,” published in the Journal of the American Chemical Society in 2022 (DOI: 10.1021/jacs.2c09026). Chemistry World’s report quotes study leader Cláudio Nunes describing the result as opening “perspectives to look at reactivity a different way.”
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