4.8 Article

Aggregation and Solvation of n-Butyllithium

Journal

ORGANIC LETTERS
Volume 19, Issue 15, Pages 3966-3969

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01644

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Funding

  1. NSF [1464538]
  2. Direct For Mathematical & Physical Scien
  3. Division Of Chemistry [1464538] Funding Source: National Science Foundation

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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 degrees 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 H-1 NMR/DOSY titration.

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