The Anomeric Effect and Associated Stereoelectronic Effects
Gregory Robert James Thatcher, American Chemical Society. Division of Carbohydrate Chemistry, American Chemical Society. Meeting
American Chemical Society, 1993 - Science - 305 pages
Discusses contemporary experimental and computational studies on the anomeric effect and related stereoelectronic effects and presents conflicting data and theories in this highly controversial area. Explores applications in carbohydrate chemistry, including enzymology, as well as organometallic chemistry and the chemistry of phosphates and sulfates. Includes examination of molecular modeling methods in compounds influenced by stereoelectronic effects.
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Some Basic Stereoelectronics
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acetal acid addition American Chemical Society analysis anomeric effect anti antiperiplanar apical atom axial basis bond angle bond length calculations chair changes charge Chem Chemistry cleavage complex component compounds conformation corresponding cyclic cyclic compounds derivatives difference dihedral angle electronic electrostatic energy equatorial evidence experimental explained favored Figure force field formation gauche geometry give given glycosides glycosyl hydrogen hydrolysis important increase indicating initio intermediate involved kcal/mol kinetic Laplacians larger leading leaving group less lone pair mechanics method methyl molecular nbcc nitrogen observed obtained optimized orbital interaction origin oxygen parameters points population position possible preference protonated reaction reactivity relative respectively reverse anomeric effect ring rotation Scheme shown similar stabilization stereoelectronic effects steric structure studies substituent suggested Table theory transition values