Aryl group π-facial electrostatic asymmetry as a contributing factor to chiral resolution on β-cyclodextrin HPLC phases
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 16,p. 1122-1124
- https://doi.org/10.1039/c39920001122
Abstract
A model based on π-facial asymmetry in the calculated molecular electrostatic potentials is proposed to account for chromatographic behaviour of phaclofen 1 and its fluorinated derivatives 2–4 on a chiral cyclodextrin stationary phase.Keywords
This publication has 14 references indexed in Scilit:
- Electrostatic vs. orbital control in π-facial diasteroselection: a PM3 SCF-MO study of electrophilic reactivity in 7-methylenenorbornanesJournal of the Chemical Society, Chemical Communications, 1992
- Rank correlation of AM1 and PM3 derived molecular electrostatic potentials (RACEL) with Hammett σp-parametersJournal of the Chemical Society, Chemical Communications, 1992
- A molecular orbital and crystallographic study of the structure and π-facial regioselectivity of 9-chloro-1,4,5,8-tetrahydro-4a,8a-methanonaphthaleneJournal of the Chemical Society, Perkin Transactions 2, 1992
- ? Facial hydrogen bonding in the chiral resolving agent (S)-2,2,2-trifluoro-1-(9-anthryl)ethanol and its racemic modificationJournal of the Chemical Society, Chemical Communications, 1991
- An AM1 and PM3 molecular orbital and self-consistent reaction-field study of the aqueous solvation of glycine, alanine and proline in their neutral and zwitterionic formsJournal of the Chemical Society, Perkin Transactions 2, 1991
- Atomic charges derived from semiempirical methodsJournal of Computational Chemistry, 1990
- Comparative study of the molecular electrostatic potential obtained from different wavefunctions. Reliability of the semiempirical MNDO wavefunctionJournal of Computational Chemistry, 1990
- Optimization of parameters for semiempirical methods II. ApplicationsJournal of Computational Chemistry, 1989
- Optimization of parameters for semiempirical methods I. MethodJournal of Computational Chemistry, 1989
- A new rapid method for orbital localisationJournal of the Chemical Society, Faraday Transactions 2: Molecular and Chemical Physics, 1982