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FAIR Data table.c Bromination of benzene
SystemaΔΔG298DOIbIRC AnimationIRC, DOIb

Benzene + 4Br2 12.2189750--
SEAr concerted substitution, Cs, 1-ve FC 36.5 189722IRC189769,189770
SEAr concerted substitution, Cs, 1-ve FC 26.5191241IRC
Bromobenzene + HBr + 3Br2 2.0 189771--
Separated Bromobenzene + HBr + 3Br2 -12.7 (-15.0)d 191252, 191253
191254,d 195500d
aClick on any energy to load a 3D-coordinate for a B3LYP+D3/6-311++G(2d,2p)/SCRF=benzene model. Relative free energies in kcal/mol, for a standard state of 0.041M. bA digital repository identifier (DOI), resolved as e.g. http://doi.org/10.14469/ch/189499 cThis FAIR datatable is assigned the persistent identifier doi:10.6084/m9.figshare.1299202 as recommended in the Joint Declaration of Data Citation Principles dAt the B2PLYPD3/6-311++D(2d,2p)/SCRF=benzene level. eIdentical to TS_1 (cis-addition). fNatural bond orbitals illustrating the interaction between the highest π-C=C occupied NBO and the axial C-Br-σ* lowest vacant NBO. gNatural bond orbitals illustrating the smaller interaction between the lower π-C=C occupied NBO and the equatorial C-Br-σ* vacant NBO. hAll attempts to locate this transition state led to direct 1,2-trans-addition instead.