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. Author manuscript; available in PMC: 2018 Jul 25.

Published in final edited form as: J Am Chem Soc. 2017 Jan 12;139(3):1233–1244. doi: 10.1021/jacs.6b11354

Plot of k_obsd vs THF concentration for the enolization of 0.0050 M oxazolidinone 9-d₂ with 0.10 M LiHMDS with THF in hexane or toluene cosolvent at −78 °C. The curves depict unweighted least-squares fits to the model described by eq 12 (vide infra). (hexane): [A]₀ is set at 0.10 M; K_eq = (1.1 ± 1) × 10⁻⁴; k₈ = (5 ± 4) × 10⁻⁴; k₉ = (8 ± 20) × 10⁻⁹; k₁₀ = (2.2 ± 1) × 10⁻⁴; k₁₁ = (7 ± 3) × 10⁻¹¹. (toluene) measured using initial rates: All parameters carried over from the fit from curve A; additionally, a = (−2 ± 1) × 10⁻⁴; b = (1.4 ± 0.9) × 10⁻⁴; c = 1.58 ± 0.06; and m = 5.

Inline graphic — Plot of k_obsd vs THF concentration for the enolization of 0.0050 M oxazolidinone 9-d₂ with 0.10 M LiHMDS with THF in hexane or toluene cosolvent at −78 °C. The curves depict unweighted least-squares fits to the model described by eq 12 (vide infra). (hexane): [A]₀ is set at 0.10 M; K_eq = (1.1 ± 1) × 10⁻⁴; k₈ = (5 ± 4) × 10⁻⁴; k₉ = (8 ± 20) × 10⁻⁹; k₁₀ = (2.2 ± 1) × 10⁻⁴; k₁₁ = (7 ± 3) × 10⁻¹¹. (toluene) measured using initial rates: All parameters carried over from the fit from curve A; additionally, a = (−2 ± 1) × 10⁻⁴; b = (1.4 ± 0.9) × 10⁻⁴; c = 1.58 ± 0.06; and m = 5.