Name
Abstract | ||
|---|---|---|
An improved method for the calculation of enantioselectivity by molecular mechanics is presented. This method does not use any a priori assumption on the conformation of the molecules in the complex and is equally applicable to weak as well as very strong complexes. High-temperature molecular dynamics is used for the creation of a large number (5000-20,000) of random conformations and configurations of a 1:1 (or 1:2) complex of chiral molecules with a chiral selector. All configurations are energy minimized. The data set is only accepted if all lowest-energy complexes occur at least five times in the minimized data set. The enantioselectivity is then calculated from the free energies of the diasteromeric complexes (chiral chromatography) or from the ratio of the sum of the boltzmann weights (distribution of enantiomers over a chiral organic phase and a nonchiral water phase). This approach has been successfully applied to a range of chiral compounds. These include a weakly bonded Pirkle chiral stationary phase (CSP) system, a strong complex of diprotonated 1,2-diphenyl-1,2-diamino-ethane with two molecules of R,R-tartrate, and the intermediate-strength complexes of protonated and of neutral norephedrine with R,R-tartrate. (C) 1995 by John Wiley & Sons, Inc. |
Year | DOI | Venue |
|---|---|---|
1995 | 10.1002/jcc.540160708 | JOURNAL OF COMPUTATIONAL CHEMISTRY |
Keywords | Field | DocType |
molecular modeling | Protonation,Chirality (chemistry),Chiral column chromatography,Molecule,Computational chemistry,Chemistry,Molecular dynamics,Boltzmann constant,Enantiomer,Molecular model | Journal |
Volume | Issue | ISSN |
16 | 7 | 0192-8651 |
Citations | PageRank | References |
1 | 0.57 | 0 |
Authors | ||
1 | ||
Name | Order | Citations | PageRank |
|---|---|---|---|
| Joep Aerts | 1 | 134 | 17.32 |