Main Title |
Nucleophilic Addition to Activated Double Bonds: Predictions of Reactivity from the Laplacian of the Charge Density. |
Author |
Carroll, M. T. ;
Cheeseman, J. R. ;
Osman, R. ;
Weinstein, H. ;
|
CORP Author |
Mount Sinai School of Medicine, New York. ;McMaster Univ., Hamilton (Ontario). Dept. of Chemistry.;Health Effects Research Lab., Research Triangle Park, NC. |
Publisher |
c1989 |
Year Published |
1989 |
Report Number |
EPA/600/J-88/544; |
Stock Number |
PB91-109256 |
Additional Subjects |
Nucleophilic reactions ;
Chemical reactivity ;
Alkene compounds ;
Unsaturated hydrocarbons ;
Harmonic functions ;
Laplace transformation ;
Charge density ;
Acrylic acids ;
Methacrylic acid ;
Acrylonitriles ;
Acroleins ;
Reprints ;
Molecular orbital method ;
AB initio calculations ;
Quantum mechanics
|
Holdings |
Library |
Call Number |
Additional Info |
Location |
Last Modified |
Checkout Status |
NTIS |
PB91-109256 |
Some EPA libraries have a fiche copy filed under the call number shown. |
|
07/26/2022 |
|
Collation |
6p |
Abstract |
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. The 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. The relative reactivities of the activated double bond in the molecules toward a nucleophilic attack, predicted by the values of Laplacian of the calculated charge density at the corresponding critical point, are in accord with experiment. The change in atomic properties of two reactants, AA and MAA, upon the nucleophilic addition of F(sup 1-) are also derived from the Laplacian of the charge density. The changes in the properties provide a quantitative description of AAF(sup 1-) and MAAF(sup 1-) carbanion formation which is related to the size of the region of charge depletion on the attacked atom. (Copyright (c) 1989 American Chemical Society). |
Supplementary Notes |
Pub. in Jnl. of Physical Chemistry, v93 n13 p5120-5123, 29 Jun 89. Prepared in cooperation with McMaster Univ., Hamilton (Ontario). Dept. of Chemistry. Sponsored by Health Effects Research Lab., Research Triangle Park, NC. |
NTIS Title Notes |
Journal article. |
Title Annotations |
Reprint: Nucleophilic Addition to Activated Double Bonds: Predictions of Reactivity from the Laplacian of the Charge Density. |
Category Codes |
99F |
NTIS Prices |
PC A02/MF A01 |
Primary Description |
600/10 |
Document Type |
NT |
Cataloging Source |
NTIS/MT |
Control Number |
034834421 |
Origin |
NTIS |
Type |
CAT |