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. 2023 Oct 20;13(44):30787–30797. doi: 10.1039/d3ra05127g

Activation energies (ΔG‡, kcal mol−1) using M06-2X/6-31+G(d) for electrocyclic ring-closure of variously functionalised 2,Y-disubstituted octatetraenes (Y = 3–7).

graphic file with name d3ra05127g-u15.jpg
R2
CH3 NH2 OH F C(O)H CN NO2
graphic file with name d3ra05127g-u16.jpg R1 CH3 14.4 16.4 14.9 14.3 17.0 12.7 17.3
NH2 17.8 18.1 15.2 14.7 16.9 13.9 16.9
OH 17.4 17.1 19.4 18.3 15.4 18.3 11.9
F 17.0 17.1 18.8 17.8 15.4 18.6 15.2
C(O)H 16.1 15.6 13.6 12.3 16.3 13.2 15.0
CN 14.0 12.9 15.0 13.8 14.5 15.9 11.5
NO2 17.9 13.3 16.4 14.8 15.5 16.3 19.0
graphic file with name d3ra05127g-u17.jpg R1 CH3 13.2 15.6 14.2 12.9 12.2 13.3 13.5
NH2 15.2 17.0 15.9 13.8 13.3 14.7 13.6
OH 15.3 17.2 16.8 16.4 13.1 14.2 13.0
F 13.7 16.8 16.1 14.1 12.1 13.7 12.4
C(O)H 11.4 13.5 12.3 9.9 8.1 10.6 8.5
CN 12.6 15.2 14.9 13.4 9.8 12.6 11.1
NO2 12.5 12.7 12.1 9.4 5.7 9.5 9.2
graphic file with name d3ra05127g-u18.jpg R1 CH3 15.7 16.2 14.3 11.1 11.9 12.8 13.1
NH2 17.1 17.5 15.2 12.5 13.7 12.0 12.5
OH 15.7 17.4 14.0 11.7 13.9 14.2 13.9
F 14.4 15.5 13.8 11.3 12.6 13.2 12.9
C(O)H 11.8 13.1 11.8 9.2 9.3 10.4 8.5
CN 14.7 12.3 12.7 10.0 10.7 12.0 12.3
NO2 9.7 9.2 11.2 8.5 7.2 10.5 6.3
graphic file with name d3ra05127g-u19.jpg R1 CH3 15.8 15.6 14.7 14.5 11.7 15.4 11.2
NH2 16.5 16.5 17.0 15.1 12.8 15.5 11.3
OH 15.6 18.3 19.9 18.0 13.3 18.0 13.9
F 17.0 17.9 16.3 15.9 13.1 18.7 12.5
C(O)H 13.2 13.8 13.5 11.6 8.4 11.7 7.3
CN 15.9 16.3 12.6 13.1 11.5 14.9 9.5
NO2 10.9 12.4 12.7 10.6 7.5 10.9 6.6
graphic file with name d3ra05127g-u20.jpg R1 CH3 11.0 13.1 13.5 13.2 8.4 10.4 6.9
NH2 15.3 16.1 15.0 9.3 11.4 7.7
OH 17.8 15.6 10.2 13.2 8.6
F 15.7 10.2 12.1 8.9
C(O)H 7.5 9.4 5.8
CN 11.4 9.0
NO2 4.9