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. Author manuscript; available in PMC: 2013 Jun 1.
Published in final edited form as: J Org Chem. 2012 Jul 31;78(5):1753–1759. doi: 10.1021/jo3011792

Table 2.

Calculated Activation Energies for ZnCl2-Catalyzed Cycloadditions of 3b with Disubstituted Furans.a

graphic file with name nihms-463527-f0017.jpg
Reactants ΔH‡ (ΔG‡) [ΔG‡soln]
syn-I anti-I syn-II anti-II
4 + 3b·ZnCl2 –13.2 (5.2) [11.5] –12.7 (4.9) [10.1] –16.1 (2.2) [7.2] –9.9 (6.8) [11.0]
5 + 3b·ZnCl2 –13.2 (4.3) [12.5] –15.5 (3.6) [11.9] –14.6 (2.6) [7.3] –13.0 (5.6) [14.1]
6 + 3b·ZnCl2 –12.8 (3.9) [8.4] –15.0 (2.3) [7.4] –12.1 (3.6) [8.0] –12.4 (3.9) [8.0]
6 + 3c·ZnCl2 –7.0 (9.7) [14.3] –8.3 (9.0) [14.4] –6.1 (9.6) [14.2] –6.0 (10.4) [14.9]
7 + 3b·ZnCl2 –9.6 (8.4) [16.1] –11.5 (4.8) [9.9] –14.4 (3.8) [11.0] –8.3 (7.0) [11.4]
a

M06-2X/6-311+G(d,p)//B3LYP/6-31G(d)–LANL2DZ. Solution-phase data incorporate CPCM solvation energies in CH2Cl2, computed at the M06-2X/6-31G(d)–LANL2DZ level. ΔH† and ΔG‡ in kcal/mol at 298.15 K.