Abstract
Various benzimidazole sulphoxides were chirally resolved employing an amylase-based chiral stationary phase. The structure-property relationships of these compounds were investigated using calculated physico-chemical properties, molecular modelling and multivariate statistical techniques. A data set of 254 molecular descriptors was used to represent the series of compounds. Analysis of the data set using principal components analysis and non-linear mapping suggested that the separation factor of each enantiomeric pair was associated with nine molecular properties and, in particular, molar refractivity of the Z substituent and the partial charge of atom 6. The separation factor of a sulphoxide not used in the analysis was well predicted thus suggesting that these models may be used to generalize.
| Original language | English |
|---|---|
| Pages (from-to) | 61-69 |
| Number of pages | 9 |
| Journal | Journal of Computer-Aided Molecular Design |
| Volume | 7 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 1 Feb 1993 |
| Externally published | Yes |
Keywords
- Computational chemistry
- Non-linear mapping
- Pattern recognition
- Principal components analysis
- Unsupervised learning