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LiCHCl 2 · 3 Pyridine, Structure of a Carbenoid with a Tetrahedral C Atom
Author(s) -
Müller Achim,
Marsch Michael,
Harms Klaus,
Lohrenz John C. W.,
Boche Gernot
Publication year - 1996
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.199615181
Subject(s) - carbenoid , chemistry , solvation , electrophile , molecule , pyridine , crystallography , atom (system on chip) , computational chemistry , tetrahedron , bond length , crystal structure , medicinal chemistry , catalysis , organic chemistry , rhodium , computer science , embedded system
CCl bonds approximately 10 pm longer than those in CH 2 Cl 2 are present in LiCHCl 2 · 3 C 5 H 5 N ( 1 ). This and the sum of the bond angles around C (308° excluding the CLi bond) confirms the increased p character of the CCl bonds and thus the pronounced electrophilicity of carbenoids. Calculations on the solvated and nonsolvated carbenoid and the comparison with experimental data reveal the remarkable influence of solvation on structure, stability, and 13 C chemical shift, which is useful for predicting the structures of such molecules in solution.