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Chromatographic optical resolution on trans ‐1,2‐diaminocyclohexane derivatives: Theory and applications
Author(s) -
Gasparrini F.,
Misiti D.,
Villani C.
Publication year - 1992
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530040709
Subject(s) - chemistry , moiety , chiral stationary phase , resolution (logic) , monomer , organic chemistry , combinatorial chemistry , matrix (chemical analysis) , chiral derivatizing agent , phase (matter) , chromatography , chiral column chromatography , polymer , artificial intelligence , computer science
An overall view on some new chiral stationary phases based on ( trans )‐1,2‐diaminocyclohexane is illustrated. The selected chiral moiety, derivatized with different aroyl groups, has been linked to a silica matrix in order to give chiral stationary phases (CSPs) enabling them to be used efficiently in the normal and reverse phase, both for analytical and preparative purposes. In addition new polymeric CSPs have been prepared by using the same selector, suitably modified, as monomer. The new chiral stationary phases have been characterised by physicochemical methods and used for the resolution of various racemic compounds classes such as α‐aryloxyacetic acids, alcohols, sulfoxides, selenoxides, phosphinates, tertiaryphosphine oxides, benzodiazepines etc. without prederivatization or as amines, amino acids, amino alcohols, nonsteroidal antiinflammatory agents in a derivatized form. The separated solutes structural variety suggests that multiple interaction sites are involved in the recognition process: some thermodynamic data relative to the CSPs—selectands interactions are also illustrated. © 1992 Wiley‐Liss, Inc.