NMR spectra of a hydrocarbon-soluble organosodium compound and its lithium analogs

Article abstract of DOI:10.1007/BF01431309

¹H, ²³Na, and ⁷Li NMR spectra of 2-ethylhexylsodium, 2-ethylhexyllithium, and isobutyllithium obtained in the reaction of the corresponding alkyl chlorides and metals have been recorded. The ¹H NMR signal for the protons of the CH₂Na group is shifted upfield compared with that for the protons of the CH₂Li group (doublets at δ -0.88 and δ -0.83, respectively). The composition of the products of reaction of 2-ethylhexyl chloride with sodium depends on the form of the metal reagent employed. The use of sodium balls with diameter up to 2 mm results in the formation of products containing ionic chlorine (30-50 % with respect to Na); the reaction with the dispersion proceeds faster and the reaction product is chlorine-free. The ²³Na NMR spectra of these substances are also different, which is explained by the formation of 2-ethylhexylsodium complexes with NaCl in the former case.