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About the Li ⊕ Gegenion Effect on α‐Sulfonyl Carbanions
Author(s) -
Gais HansJoachim,
Hellmann Gunther,
Lindner Hans Jörg
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199001001
Subject(s) - carbanion , sulfonyl , chemistry , dimer , lithium (medication) , ring (chemistry) , monomer , medicinal chemistry , crystal structure , crystallography , stereochemistry , organic chemistry , polymer , medicine , alkyl , endocrinology
To what extent do the structure and dynamics of the α‐sulfonyl carbanion l ⊖ depend on the gegenion? As shown by the X‐ray structure analyses of the lithium‐ and tetrabutylammonium salts, these are present in the crystal as a dimer ( 1 ⊖ /Li ⊕ · 2THF) 2 with an eight‐membered (SOLiO) 2 ring and as a monomer 1 ⊕ /NBu 4 with discrete cations and anions, respectively. In contrast, the C α S rotation barrier of 1 ⊖ is hardly influenced by NBu 4 ⊕(in THF or DMSO) and K ⊕ (in DMSO).
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