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- W2899966021 abstract "Post Hartree–Fock and density functional theory methods have been employed to study inside-protonated 1-azaadamantane 7 and its complexes with the fluoride counterion (contact ion pairs) 10 and 11. The study also involved 1-azaadamantane 4, its outside-protonated form 8, and 1-azaadamantane radical cation 17. Inside-protonated 1-azaadamantane 7 is more than 82 kcal mol −1 less stable than out-isomer 8. The repulsive interaction between the internal N + –H group and the azaadamantane cage and a substantial deformation of this cage greatly weaken the C–N and C–C bonds and, consequently, lead to a low kinetic stability of in-ion 7 in the studied unimolecular and bimolecular reactions involving the removal of the encapsulated proton from the cage. Among these reactions, a 7 → 8 rearrangement through a reversible cage opening at the C–N bond was found to be the main transformation channel ([Formula: see text] < 16 kcal mol −1 ) for in-ion 7. This rearrangement can be catalyzed by an external base, e.g., the fluoride anion. A 1,4-hydrogen migration in 1-azaadamantane radical cation 17 as a possible pathway to the inside-protonated 1-azaadamantane 7 was explored. It was found that this process has a prohibitively high activation barrier, [Formula: see text] > 104 kcal mol −1 , and is not able to compete with the α-C–C cleavage of the azaadamantane cage ([Formula: see text] < 26 kcal mol −1 )." @default.
- W2899966021 created "2018-11-16" @default.
- W2899966021 creator A5012145334 @default.
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- W2899966021 date "2019-03-01" @default.
- W2899966021 modified "2023-09-26" @default.
- W2899966021 title "Inside-protonated 1-azaadamantane: computational studies on the structure, stability, and generation" @default.
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- W2899966021 doi "https://doi.org/10.1139/cjc-2018-0407" @default.
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