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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 tetrahydrofuran (THF) concentration²⁵ for the enolization of 0.0050 M oxazolidinone 9 with 0.10 M lithium hexamethyldisilazide (LiHMDS) with THF in hexane ( ) and toluene ( ) at −78 °C. The curve depicts an unweighted least-squares fit to the composite model described by eq 12 (vide infra). (hexane): [A]₀ is set at 0.10 M; K_eq = (2.3 ± 0.2) × 10⁻⁴; k₈ = (3.9 ± 0.1) × 10⁻²; k₉ = (2 ± 10) × 10⁻⁸; k₁₀ is set to 2.0 × 10⁻⁴; k₁₁ = (5 ± 4) × 10⁻¹⁰. (toluene): All parameters carried over from the fit from curve A; additionally, a = −3.19 × 10⁻⁵; b = 3.36 × 10⁻⁵; c is set at 1.0; and m = 4.81.

Inline graphic — Plot of k_obsd vs tetrahydrofuran (THF) concentration²⁵ for the enolization of 0.0050 M oxazolidinone 9 with 0.10 M lithium hexamethyldisilazide (LiHMDS) with THF in hexane ( ) and toluene ( ) at −78 °C. The curve depicts an unweighted least-squares fit to the composite model described by eq 12 (vide infra). (hexane): [A]₀ is set at 0.10 M; K_eq = (2.3 ± 0.2) × 10⁻⁴; k₈ = (3.9 ± 0.1) × 10⁻²; k₉ = (2 ± 10) × 10⁻⁸; k₁₀ is set to 2.0 × 10⁻⁴; k₁₁ = (5 ± 4) × 10⁻¹⁰. (toluene): All parameters carried over from the fit from curve A; additionally, a = −3.19 × 10⁻⁵; b = 3.36 × 10⁻⁵; c is set at 1.0; and m = 4.81.