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Liu, Y; Sanchez, D M; Ware, M R; Champenois, E G; Yang, J; Nunes, J P F; Attar, A; Centurion, M; Cryan, J P; Forbes, R; Hegazy, K; Hoffmann, M C; Ji, F; Lin, M-F; Luo, D; Saha, S K; Shen, X; Wang, X J; Martínez, T J; Wolf, T J A
Nature communications, 05/2023, Volume: 14, Issue: 1Journal Article
Electrocyclic reactions are characterized by the concerted formation and cleavage of both σ and π bonds through a cyclic structure. This structure is known as a pericyclic transition state for thermal reactions and a pericyclic minimum in the excited state for photochemical reactions. However, the structure of the pericyclic geometry has yet to be observed experimentally. We use a combination of ultrafast electron diffraction and excited state wavepacket simulations to image structural dynamics through the pericyclic minimum of a photochemical electrocyclic ring-opening reaction in the molecule α-terpinene. The structural motion into the pericyclic minimum is dominated by rehybridization of two carbon atoms, which is required for the transformation from two to three conjugated π bonds. The σ bond dissociation largely happens after internal conversion from the pericyclic minimum to the electronic ground state. These findings may be transferrable to electrocyclic reactions in general.
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