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J O U R N A L O F T H E A M E R I C A N C H E M I C A L S O C I E T Y
 

Summary: J O U R N A L
O F T H E A M E R I C A N C H E M I C A L S O C I E T Y
Registered in US. Patent Office. 0 Copyright, 1976, by the American Chemical Society
VOLUME98, NUMBER18 SEPTEMBER1, 1976
Stabilization of Planar Tetracoordinate Carbon a
John B. Collins,lb*cJames D. Dill,lbEluvathingal D. Jemmis,lb*cYitzhak Apeloig,Ib
Paul von R. Schleyer,*lb,CRolf Seeger,ldand John A. Popleld
Contributionfrom the Departments of Chemistry, Princeton University,
Princeton, New Jersey 08540, Institut fur Organische Chemie, Universitat Erlangen-
Nurnberg, 0-8520 Erlangen, Germany,and Carnegie-Mellon University,Pittsburgh,
Pennsylvania 15213. Received August 26, 1975
Abstract: The energies of planar vs. tetrahedral geometries of tetracoordinateorganic moleculeshave been surveyed by ab ini-
tio molecular orbital calculations. Because of their 7~ acceptor and u donor character, electropositive substituents, especially
lithium, are particularly effective in stabilizing the planar arrangements selectively.Multiple substitution by such metals and
by three-membered rings provides further stabilization, and 1,l-dilithiocyclopropane(XVII) and 3,3-dilithiocyclopropene
(XVIII), inter alia, are actually calculated (RHF/STO-3G theory) to be more stable planar than tetrahedral.
van't Hoff and LeBel's proposal that tetracoordinate car-
bon prefers tetrahedral geometry2celebrated its centenary in
1974.3 No fundamental exception, e.g., an organic compound
in which all four substituents lie in a plane, is known. It is not

  

Source: Apeloig, Yitzhak - Department of Chemistry, Technion, Israel Institute of Technology

 

Collections: Chemistry