Organic Letters
Organic Letters
5 years ago

Aggregation and Solvation of n-Butyllithium

Aggregation and Solvation of n-Butyllithium
Russell Hopson, Paul G. Williard, Onkei Tai
Solution characterizations and ligand binding constants were determined for n-butyllithium in hydrocarbon and ethereal solvents using diffusion-ordered NMR. In hydrocarbon solvents, n-butyllithium exists primarily as an octamer at −40 °C and deaggregates to a hexamer when the temperature is increased. In the presence of THF or diethyl ether, n-butyllithium exists predominantly as a tetra-solvated tetramer and deaggregates to a tetra-solvated dimer in the presence of a large excess or neat THF. The ligand binding constants for the tetra-solvated tetramers were measured using 1H NMR/DOSY titration.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01644

DOI: 10.1021/acs.orglett.7b01644

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