ISSN:
0192-8651
Keywords:
Computational Chemistry and Molecular Modeling
;
Biochemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Computer Science
Notes:
The AM1 calculation was done for ortho-substituted toluenes (o-X-C6H4-CH3) and ortho-substituted tert-butylbenzenes (o-X-C6H4-t-Bu). The difference in the calculated heat of formation between o-X-C6H4-CH3 and o-X-C6H4-t-Bu was used as a theoretical steric index for ortho-X. The correlation of this theoretical steric index with the empirical steric parameter sets such as our recently defined Es(AMD) and the Taft-Kutter-Hansch (TKH) Es was examined. In spite of the simplicity of the model system, the theoretical index was linear with the Es(AMD) constant with a correlation coefficient of r = 0.972 for 17 substituents of various structures. Including the phenyl group, the correlation with the TKH Es constant was r = 0.948. The theoretically calculated index was shown to serve as a measure of the ortho steric effect.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jcc.540120115
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