Abstract
Knowing the eutectic composition of the binary melting point phase diagrams of the diastereomeric salts formed during the given resolution, the achievable F (F = eeDia*Y) value can be calculated. The same value can also be calculated and predicted by knowing the eutectic compositions of the binary melting point phase diagrams of enantiomeric mixtures of the racemic compound or the resolving agent. An explanation was sought as to why and how the crystalline precipitated diastereomeric salt—formed in the solution between a racemic compound and the corresponding resolving agent—may be formed. According to our idea, the self-disproportionation of enantiomers (SDE) has a decisive role when the enantiomers form two nonequal ratios of conformers in solution. The self-organized enantiomers form supramolecular associations having M and P helicity, and double helices are formed. Between these double spirals, with the formation of new double spirals, a dynamic equilibrium is achieved and the salt crystallizes. During this process between acids and bases, chelate structures may also be formed. Acids appear to have a crucial impact on these structures. It is assumed that the behavior of each chiral molecule is determined by its own code. This code validates the combined effect of constituent atoms, bonds, spatial structure, charge distribution, flexibility and complementarity.
Highlights
When a racemic mixture (SR) reacts in a solution with a suitable chiral compound (R*), depending on the solvent, one of the diastereomers precipitates and the other remains in solution (RR* solution)
The multiplication of the purity and yield (Y) of the enantiomeric mixture, which is isolated from the precipitated diastereomer, gives the selectivity (F = eeDia*Y)
We have shown experimentally [1] that under certain conditions the purity of the enantiomeric mixtures separable from the precipitated diastereomeric salt is approximately equal to the eutectic composition of the enantiomeric mixtures of the racemic compound or the eutectic composition of the enantiomeric mixtures of the resolving agent
Summary
When a racemic mixture (SR) reacts in a solution with a suitable chiral compound (R*), depending on the solvent, one of the diastereomers precipitates (e.g., crystalline SR*) and the other remains in solution (RR* solution). We have shown experimentally [1] that under certain conditions the purity of the enantiomeric mixtures separable from the precipitated diastereomeric salt is approximately equal to the eutectic composition of the enantiomeric mixtures of the racemic compound or the eutectic composition of the enantiomeric mixtures of the resolving agent (eeDia~eeEuRac or eeDia~eeEuRes). ETuEhnuedtSetcootiircchCtihooemmpeetoursytietoicoftntihcoefcCEoriytmhsteparloltihsneietRiDoaicnaesmtoeifrcetCohmoemerpeiconuSananldttioMoramthyeeBrReiecDsoemtlevirixmntgiunAregedesbnytof the reso (eeDiaB~aeseedEuoRnacouorroewenD[ia2~–e4]eaEnudReos)t.hers’ experimental results regarding the self- disproportionatTiohneofeennannttioiommeres r(SsD—E)w[5h–o16s]e, wseewpearrealtoiookningpfoosrsainbeixliptliaensataiorneosf uthme pmosasribilzeed in t hmaevcehabneisemn fuosretdhefdoirsttrhibeutsiyonntohf ethsieseonfanatciotimveeripc hdaiarsmteraecoemuetriiccamliixntugrreesdbieetwntesen(Jumex dsoinlisd,H–laioqswupeidavreptrh,aatmhseeesr.e, wCahslonoroecxipdla,naantiotinboiof thiocws)i.tDisuproisnsigblethtoe froermsotlhuetieountecotifc tchomes-e comp tphoesritiionnsiogf hthtes shinagvlee ebneaenntioamdedr eredsotlovinoguargpenret vfrioomutshke nenoawntlieomdgeres.of the racemic compound present. We believe that this is only possible if at least two reactive conform-.
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