Stereochemistry of reaction paths at carbonyl centres

Abstract Results of recent experimental and theoretical studies of nucleophilic addition to carbonyl groups are described. The reaction paths found by different methods for different nucleophiles show some striking similarities that appear to be characteristic for the reaction type.

[1]  Jack D. Dunitz,et al.  Geometrical reaction coordinates. II. Nucleophilic addition to a carbonyl group , 1973 .

[2]  Leo Radom,et al.  Molecular orbital theory of the electronic structure of organic compounds. XIII. Fourier component analysis of internal rotation potential functions in saturated molecules , 1972 .

[3]  L. Salem,et al.  Superjacent orbital control. Interpretation of the anomeric effect , 1973 .

[4]  O. Eisenstein,et al.  35Cl pure quadrupole resonance in acetylated glycopyranosyl chlorides. Relation between chlorine nuclear quadrupole coupling constant and molecular conformation , 1973 .

[5]  C. Hoffman,et al.  The Molecular Structure of Carbon Tetrafluoride , 1953 .

[6]  J. Lehn,et al.  Stereoelectronic Properties of Tetrahedral Species derived from Carbonyl Groups. Ab initio study of the hydroxymethanes , 1974 .

[7]  C. C. Costain,et al.  A NEW CRITERION FOR THE DETERMINATION OF MOLECULAR STRUCTURES FROM GROUND STATE ROTATIONAL CONSTANTS , 1958 .

[8]  M. Sundaralingam,et al.  Some aspects of stereochemistry and hydrogen bonding of carbohydrates related to polysaccharide conformations , 1968 .

[9]  Leo Radom,et al.  The application of ab initio molecular orbital theory to the anomeric effect. A comparison of theoretical predictions and experimental data on conformations and bond lengths in some pyranoses and methyl pyranosides , 1972 .

[10]  C. Moreau,et al.  The Importance of Conformation in the Ozonolysis of Acetalsl , 1972 .

[11]  D. Koshland,et al.  Effect of small changes in orientation on reaction rate , 1972 .

[12]  W. Gordy,et al.  Microwave Spectra and Molecular Structures of Fluoroform, Chloroform, and Methyl Chloroform , 1952 .

[13]  J. Guthrie.  Hydration of carboxylic acids and esters. Evaluation of the free energy change for addition of water to acetic and formic acids and their methyl esters , 1973 .

[14]  E. Lucken,et al.  Nuclear Quadrupole Resonance and Stereochemistry I. α – Chloro ethers , 1973 .

[15]  H. Buergi.  Chemical reaction coordinates from crystal structure data. I. , 1973 .

[16]  L. C. Snyder,et al.  Heats of reaction from self-consistent-field energies of closed-shell molecules , 1969 .

[17]  J. Kirsch.  Mechanism of enzyme action. , 1973, Annual review of biochemistry.

[18]  Roald Hoffmann,et al.  Interaction of orbitals through space and through bonds , 1971 .