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Solid‐State Structure of a Li/F Carbenoid: Pentafluoroethyllithium
Author(s) -
Waerder Benedikt,
Steinhauer Simon,
Neumann Beate,
Stammler HansGeorg,
Mix Andreas,
Vishnevskiy Yury V.,
Hoge Berthold,
Mitzel Norbert W.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201406564
Subject(s) - carbenoid , reactivity (psychology) , chemistry , solid state , dimer , nuclear magnetic resonance spectroscopy , lithium (medication) , molecule , crystallography , alkyl , silyl ether , diethyl ether , stereochemistry , computational chemistry , organic chemistry , silylation , medicine , alternative medicine , pathology , rhodium , endocrinology , catalysis
Lithium carbenoids are versatile compounds for synthesis owing to their intriguing ambiphilic behavior. Although this class of compounds has been known for several years, few solid‐state structures exist because of their high reactivity and often low thermal stability. Using cryo X‐ray techniques, we were now able to elucidate the first solid‐state structure of a Li/F alkyl carbenoid, pentafluoroethyllithium (LiC 2 F 5 ), finally yielding a prototype for investigating structure—reactivity relationships for this class of molecules. The compound forms a diethyl ether‐solvated dimer bridged by a rare C–F–Li link. Complementary NMR spectroscopy studies in solution show dynamic processes and indicate rapid exchange of starting material and product. Theoretical investigations help to understand the formation of the observed unusual structural motif.