In:
Collection of Czechoslovak Chemical Communications, Institute of Organic Chemistry & Biochemistry, Vol. 52, No. 12 ( 1987), p. 2971-2982
Abstract:
Base-catalyzed oxirane ring-opening reaction of 4,5-epoxy-2-oxapentyl crown ethers Ia-Ie and N-(2,3-epoxy-1-propyl) azacrown ethers IIa-IIc with adenine affords mixtures of corresponding adenin-9-yl, adenin-3-yl and adenin-7-yl derivatives ( IIIa-IIIe, IVa-IVe, Va-Ve, VIa-VIc, VIIa-VIIc and VIIIa-VIIIc ) respectively, separable by liquid chromatography. Structure of the individual isomers was assigned on basis of 1 H, and 13 C NMR spectroscopy. Compexation of the prevailing (adenin-9-yl) isomers IIIa-IIIe and VIa-VIc with sodium ion was measured potentiometrically in 99% methanol and the calculated stability constants were compared with corresponding data from related homologous series of crown and azacrown ethers IXa-IXe, Xa-Xe, XIa-XIc and XIIa-XIIc differing in pendant group.
Type of Medium:
Online Resource
ISSN:
0010-0765
,
1212-6950
DOI:
10.1135/cccc19872971
Language:
English
Publisher:
Institute of Organic Chemistry & Biochemistry
Publication Date:
1987
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