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Maßgeschneiderte Wirtverbindung für Piperazin und verwandte Amine
Author(s) -
Hoss Ralf,
Vögtle Fritz
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260421
Subject(s) - chemistry , piperazine , diamine , catechol , bicyclic molecule , hydrochloric acid , amine gas treating , medicinal chemistry , tris , yield (engineering) , stereochemistry , polymer chemistry , organic chemistry , biochemistry , materials science , metallurgy
Tailor‐Made Host for Piperazine and Related Amines The 38‐membered bis‐catechol 4b is obtained by cyclisation of the diacyl dichloride 3c with the diamine 2b in 45% yield, whereas a 68‐membered octalactam 7 is formed under similar conditions from 5 and 1b . Bis‐catechol 4b is a selective host compound for piperazine ( 8 ) and the structurally related diamine 9 . Association constants for the 1:1 complexes have been measured by 1 H‐NMR titration experiments. A nucleobase guest (pterine, 24 ) was extracted into a hydrochloric acid phase by complex formation with the host 4b . The results are compared with solubility and transport experiments obtained by use of analogous macro bicyclic tris‐catechol hosts.