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Updated: May 14, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Conformational equilibria of N,N-dimethylsuccinamic acid and its lithium salt as a function of solvent
Albert Tianxiang Liu1, Bright U Emenike, William R Carroll
1Gates and Crellin Laboratories of Chemistry, California Institute of Technology, Pasadena, California 91125, United States.
Abstract:
The conformational preferences of N,N-dimethylsuccinamic acid and its Li(+) salt were estimated by comparing the respective experimental NMR vicinal proton-proton coupling constants to semiempirical coupling constants for each staggered conformer as derived by the Haasnoot-De Leeuw-Altona method. The strong gauche preferences for the Li(+) salts clearly depended more on the solvents' hydrogen-bond donating strength (α) than on their hydrogen-bond accepting (β) counterpart, where α and β are the corresponding Kamlet-Taft parameters.
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