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FAIR Data table.a Computed relative reaction free energies (kcal/nol-1) of Obtusallene derived oxonium and chloronium cations
Epoxide ring opening/oxonium cation formation
Ring opening the epoxideReactant: 0.0 , bj96b
Product: -17.5 , bj83
TS C13: 1.5 , bjmx TS C12: 0.9 , bkr9
Oxonium ion pair
C-O NBOC6-O C9-O C12-O, bnc8
Nucleophilic attack on oxonium cation
NucleophileC6C9C12
MeOH 21.9c bfd2 23.2 , bjqc
32.1d bfcs
21.3, bfcr
0.0 , bj96 (reactant), 2.0 , bj99 (product)
2MeOH- 26.4 , bjnj 18.8 , bjmw
0.0 , bnhz (reactant)
Br(-) 18.0 (16.1D) bfcj 17.5 (14.5D), bfck14.7 (11.1D), bfcm
0.0, bnrd (reactant)
MeO(-) 21.1 (15.5D), bfcn 18.6 (15.5D), bfcp10.9 (11.0D), bfcq
0.0 , bnh6 (Reactant)
Nucleophilic attack on chloronium cation
MeOH14.7 , bj8z 15.8 , bj95 16.2 , bj82
0.0 , bnc7 (reactant)
Nucleophilic attack on oxonium cation/BF4 anion ion-pair
MeOH20.0 (24.5D), bksg 20.3 (15.0D), bj97 20.5 , bj98
0.0 , bnhq (reactant)
aClick on any energy to load a 3D-coordinate for a ωB97XD/Def2-TZVPPD/SCRF=methanol model. bRDM (Research data management) DOI, resolved as e.g. http://doi.org/bj96 cΔG298 for transition state, kcal mol-1 dAlternative conformation for 8-ring.