Norcaradiene−Cycloheptatriene Equilibrium: A Heavy-Atom Quantum Tunneling Case
2024
Corchado Martín-Romo, Jose Carlos | Cintas Moreno, Pedro | Babiano Caballero, Reyes | García de la Concepción, Juan | Corchado Martín-Romo, José Carlos | Universidad de Extremadura. Instituto Universitario de Investigación del Agua, Cambio Climático y Sostenibilidad (IACYS) | Universidad de Extremadura. Departamento de Ingeniería Química y Química Física | Universidad de Extremadura. Departamento de Química Orgánica e Inorgánica | Universidad de Extremadura. Instituto de Computación Científica Avanzada de la Universidad de Extremadura (ICCAEx)
The equilibrium between norcaradiene and cycloheptatriene, which has captivated chemists for more than half a century, is revisited by state-of-the-art quantum chemical calculations. Our theoretical data significantly deviate from the experimental results (J. Am. Chem. Soc., 1981, 26, 7791–7792), especially at low temperatures, where isomerization is dominated by heavy-atom tunneling. This effect results in an extremely short half-life for norcaradiene, rendering it undetectable. This work sheds light on this equilibrium, updating the kinetic and thermodynamic data while also expanding the repertoire of organic reactions controlled by this exotic quantum effect.
Show more [+] Less [-]This work was supported by the Spanish State Research Agency (AEI) through project number PID2022-136814NBI00.
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