A set of chiral sulphoxides was chromatographed on four chiral stationary phases (CSPs), using cellulose and amylose tris-phenylcarbamates coated onto 3-aminopropyl mesoporous silica. The relative retention and enantioselectives of the solutes were compared to molecular connectivity indices, similarity and holistic descriptors calculated by 3D-WHIM. Many quantitative structure-enantioselective retention relationships were developed to describe the enantioselective chromatographic performance. The same dataset was used for all CSPs, and it was possible to reveal a clear distinction between them, i.e. there was a molecular recognition pattern established according to CSPs. Results also showed that log k could be predicted for both sulphoxide enantiomers, but α was not discriminated.