doi:10.1016/S0097-8485(00)00078-4
Copyright © 2001 Elsevier Science Ltd. All rights reserved.
A QSPR model for the prediction of the gas-phase free energies of activation of rotation around the N---C(O) bond
Jaan Leis
,
and Mati Karelson
Department of Chemistry, University of Tartu, 2 Jakobi Street, Tartu 51014, Estonia
Received 13 January 2000;
accepted 11 April 2000.
Available online 31 January 2001.
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Abstract
A novel approach to predict the gas-phase rotational activation energies of amides is presented. The quantitative structure property relationship (QSPR) treatment, using the statistical package, comprehensive descriptors for structural and statistical analysis (CODESSA), resulted in a three-parameter equation with R2=0.982 for the ΔG≠gas, of a set of 24 N,N-dialkylamides.
Author Keywords: QSAR/QSPR; Amides; Rotation barriers
Fig. 1. Plot of the experimental (ΔG≠gas) vs. QSPR calculated (ΔG≠calc) free energies of activation for the amide bond rotation.
Table 1. The amides, R1C(O)NR2R3, used in study and their experimental gas-phase free energies of activation for the amide bond rotation

Table 2. The descriptors involved in the best three-parameter model (24 compounds) derived for ΔG≠gasa

Table 3. The values of descriptors and experimental, ΔG≠gas, and calculated, ΔG≠calc values of free energy of activation for each of the 24 compounds used in the study

Table 4. The best one-, two- and three-parameter modelsa for the set (B) of 15 N,N-di-substituted amides

Table 5. The predicted and experimentally determined free energies of activation and their difference for the amide bond rotation of the test set (C) of compounds
