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NUCLEOPHILIC ADDITION TO ACTIVATED DOUBLE BONDS: PREDICTION OF REACTIVITY FROM THE LAPLACIAN OF CHARGE DENSITY
Citation:
Carroll, Cheeseman, Osman, AND Weinstein. NUCLEOPHILIC ADDITION TO ACTIVATED DOUBLE BONDS: PREDICTION OF REACTIVITY FROM THE LAPLACIAN OF CHARGE DENSITY. U.S. Environmental Protection Agency, Washington, D.C., EPA/600/J-88/544 (NTIS PB91109256), 1988.
Description:
The reactivities of a series of molecules in a Michael addition reaction are analyzed on the basis of properties expressed in the Laplacian of the charge density distribution. he charge densities of structurally optimized acrylic acid (AA), methacrylic acid (MAA), acrylonitrile (ACN) and acrolein (ACR) have been calculated by ab-initio quantum mechanical methods with various basis sets. he relative reactivities of the activated double bond in these molecules toward a nucleophilic attack, predicted by the values of the corresponding critical point, are in accord with experiment. he change in atomic properties of two reactants, AA and MAA, upon the nucleophilic addition of F- are also derived from the Laplacian of the charge density. he changes in these properties provide a quantitative description of AAF- and MAAF- carbanion formation which is related to the size of the region of charge depletion on the attacked atom.
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NUCLEOPHILIC ADDITION TO ACTIVATED DOUBLE BONDS: PREDICTION OF REACTIVITY FROM THE LAPLACIAN OF CHARGE DENSITY