Molecular structure of the lithium enolate of acetaldehyde

Journal Article · Fri Nov 21 00:00:00 EST 1980 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo01312a045· OSTI ID:6604886

Lynch, T J; Newcomb, M; Bergbreiter, D E; Hall, M B

Calculations of the structures of isomers of the lithium enolate of acetaldehyde done at the restricted Hartree-Fock level with the HONDO program on the CDC 7600 are reported. Using the standard 4-31 G basis set, these calculations produce excessively large bond angles, and this favors the most open of the three isomeric structures. Including the polarization functions on the carbons and oxygen and using the recent Dunning and Hayes (3s2p/2s) contraction indicates that the chirol enolates are the lowest energy structure. However, the differences of the various enolate structures are small and could be modified by solvent effects. These results are proported to suggest that the enolates containing internal ligands may be prepared such that a new chirol center would exist by virtue of the counterion position. (BLM)

• Research Organization: Texas A and M Univ., College Station
• DOE Contract Number: W-7405-ENG-48
• OSTI ID: 6604886
• Journal Information: J. Org. Chem.; (United States), Vol. 45:24
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
ALDEHYDES
MOLECULAR STRUCTURE
ENOLS
LITHIUM COMPOUNDS
ORGANOMETALLIC COMPOUNDS
EXPERIMENTAL DATA
ALCOHOLS
ALKALI METAL COMPOUNDS
DATA
HYDROXY COMPOUNDS
INFORMATION
NUMERICAL DATA
ORGANIC COMPOUNDS
400201* - Chemical & Physicochemical Properties
400301 - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)