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- W4244164709 abstract "Abstract The photochemical rearrangement of o ‐nitrobenzaldehyde to o ‐nitrosobenzoic acid, first reported in 1901, has been shown to proceed via a distinct ketene intermediate. In the course of matrix isolation experiments in various host materials at temperatures as low as 3 K, the ketene was re‐investigated in its electronic and vibrational ground states. It was shown that hitherto unreported H‐tunneling dominates its reactivity, with half‐lives of a few minutes. Unexpectedly, the tunneling product is different from o ‐nitrosobenzoic acid formed in the photoprocess: Once prepared by irradiation, the ketene spontaneously rearranges to an isoxazolone via an intriguing mechanism initiated by H‐tunneling. CCSD(T)/cc‐pVTZ computations reveal that this isoxazolone is neither thermodynamically nor kinetically favored under the experimental conditions, and that formation of this unique tunneling product constitutes a remarkable and new example of tunneling control." @default.
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- W4244164709 date "2017-07-04" @default.
- W4244164709 modified "2023-09-25" @default.
- W4244164709 title "Formation of a Tunneling Product in the Photorearrangement of <i>o</i> -Nitrobenzaldehyde" @default.
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- W4244164709 doi "https://doi.org/10.1002/ange.201705140" @default.
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