Abstract
An IR spectroscopic study is reported of diphenylmethyllithium (DPM −Li +) in the three solvents diethyl ether, tetrahydrofuran and dimethoxyethane. Bands corresponding to the skeletal in-plane stretching vibration (ν CC), the out-of-plane ring deformation ( øcc) and the aromatic C-H out-of-plane bending vibration (γ C-H) in the carbanion have been identified. Frequency shifts with respect to the parent diphenylmethane (DPM) are in accord with charge delocalization in the carbanion. The solvent dependence of the ν CC and φ CC bands is discussed in terms of various types of ion-pair species (contact, externally solvated contact, solvent-separated). The interpretation of the IR results is in general agreement with previous studies of DPM −Li + in ethereal solvents by electronic absorption and 13C NMR spectroscopy. Limitations of this approach in the study of ion-pairing and solvation phenomena of carbanions are outlined.
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