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. Author manuscript; available in PMC: 2018 Oct 30.
Published in final edited form as: J Am Chem Soc. 2016 Nov 30;138(49):15903–15910. doi: 10.1021/jacs.6b05797

Figure 6.

Figure 6.

DFT-optimized structures of substituted benzoquinones: (a) 64, showing the hydrogen bonds between the substituent -OH and the C=O in the neutral quinone state (Q); (b) 64, showing the hydrogen bonds between the substituent C=O and the –OH in the hydroquinone state (H2Q); (c) 61, showing the hydrogen bonds between the substituent C=O and the –OH in the hydroquinone state; (d) 21, showing the hydrogen bond between the SO3– substituent and the –OH in the hydroquinone state; and (e) 114, showing the nonplanar six-membered ring and the out-of-plane proton positions to illustrate steric effects.