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. Author manuscript; available in PMC: 2018 Jul 25.
Published in final edited form as: J Am Chem Soc. 2017 Oct 16;139(42):15197–15204. doi: 10.1021/jacs.7b08734

Figure 1.

Figure 1

Plot of 1,3-dimethoxybenzene (20, ArH) concentration versus time for stoichiometric orthometalation with 0.10 M NaDA in 5.83 M THF/hexane at −78 °C. The curve depicts an unweighted least-squares fit to the function18,21 [ArH] = {[ArH]s1−n + k(n−1)t}1/(1−n) + [ArH]∞: [ArH]s = 0.0368 ± 0.0004; n = 0.71 ± 0.03; k = (4.1 ± 0.4) × 10−4; [ArH]∞ = 0.0616 ± 0.0003. The deviation from 1.5-order behavior (first order in arene and one-half order in NaDA) is likely due to mild autocatalysis.