Predicting thermochemical parameters of oxygen-containing heterocycles using simple QSPR models
-
Adams, Nico; Clauss, Joachim; Meunier, Marc; Schubert, Ulrich S.
- Abstract:
- Quantitative structure – property relationships for the prediction of standard enthalpies and entropies of formation as well as
standard molar heat capacities for small oxygen heterocyclic compounds were developed, using 1D, 2D and 3D descriptors
and experimental or computed thermochemical data. To develop the models, the data set was split into test and training sets
using D-optimal experimental design to generate a diverse training set. Internal (R 2
cross-validated ¼ 0.898 2 0.998) and
external (R 2
cross-validated ¼ 0.847 2 0.996) validation showed the models to be both stable and highly predictive. Enthalpies of
formation were best described by electrotopological, atomic composition and molecular refractivity descriptors, while Kier
and Hall x and k descriptors as well as the number of rotatable bonds appear frequently in models describing the entropy of
formation of these compounds. Heat capacity models often feature the molecular area descriptor as well as the Kier and Hall
0x descriptor and the number of methyl groups present in the molecule.
- Year:
- 2006
- Type of Publication:
- Article
- Journal:
- Molecular Simulations
- Volume:
- 32
- Number:
- 2
- Pages:
- 125 - 134