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Separation of organic bases by Craig distribution. III. Distribution behavior of diastereoisomeric N,N'-dibutyl-alpha ,alpha '-diphenylethylenediamines

Schönenberger, Helmut and Brinkmann, R. and Bamann, E. (1964) Separation of organic bases by Craig distribution. III. Distribution behavior of diastereoisomeric N,N'-dibutyl-alpha ,alpha '-diphenylethylenediamines. Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 297 (1), pp. 51-58.

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Abstract

cf. CA 52, 18274h; 60, 4033c. dl-(BuNHCHPh)2.2HCl (I.2HCl) and meso-I.2HCl showed different distribution behavior under certain conditions. Thus, in the system 10:1:9 CHCl3-MeOH-buffer at 22 Deg, the compds. showed the following solubilities [compd., g. salt in 100 ml. aq. phase (pH 1), and g. salt in 100 ml. org. phase given]: meso-I, 9.8, 1.3; dl-I, 9.2, 38.2. While, in the distribution of amines between buffer solns. and org. solvents, as a rule only the undissocd. bases enter into the distribution equil. and the dissocd. fraction is found solely in the aq. phase, dl-I and meso-I were distributed as salts under certain conditions. This deviating behavior was the reason for very large sepn. effects. This could be attributed to conformational differences and to easier formation of a hydrate shell with meso-I than with dl-I.

Item Type:

Article

Additional information (public):

CAN 60:64904 6 Phase Equilibriums, Chemical Equilbriums, and Solutions 67-66-3 (Chloroform) (mixts. of, with MeOH, N,N'-dibutyl-alpha ,alpha '-diphenylethylenediamine partition between aq. soln. and); 67-56-1 (Methanol) (mixts. with CHCl3, N,N'-dibutyl-alpha ,alpha '-diphenyl-ethylenediamine partition between aq. solns. and); 96504-88-0 (Ethylenediamine, N,N'-dibutyl-1,2-diphenyl-, dihydrochloride, (+-)-); 96504-88-0 (Ethylenediamine, N,N'-dibutyl-1,2-diphenyl-, dihydrochloride, meso-) (partition between aq. solns. and org. solvents)

Institutions:

Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger

Identification Number:

Value	Type
1964:64904	Other

Keywords:

Conformation (of N,N'-dibutyl-1,2-diphenylethylenediamine, partition between aq. solns. and org. solvents in relation to) Partition (of N,N'-dibutyl-alpha ,alpha '-diphenylethylenediamines between aq. soln. and org. solvents) Hydration (chemical) (N,N'-dibutyl-alpha ,alpha '-diphenylethylenediamine partition between aq. solns. and org. solvents in relation to)

Subjects:

500 Science > 540 Chemistry & allied sciences

Status:

Published

Refereed:

Yes, this version has been refereed

Created at the University of Regensburg:

Unknown

Owner:

Petra Gürster

Deposited On:

19 Nov 2010 10:29