93000-66-9Relevant academic research and scientific papers
Syntheses of Calcium-Selective, Substituted Diaza-Crown Ethers: A Novel, One-Step Formation of Bibracchial Lariat Ethers (BiBLEs)
Gatto, Vincent J.,Gokel, George W.
, p. 8240 - 8244 (1984)
Ten N,N-disubstituted derivatives of 4,13-diaza-18-crown-6 (7) have been prepared, three of which exhibit Ca2+, over either Na+ or K+, selectivity.This selectivity has been achieved by utilizing polar, yet uncharged, donor groups such as carbethoxymethyl.Several of these compunds have been prepared by a novel, one-step reaction of aliphatic primary amines with triethylene glycol diiodide.The compounds prepared by this method include examples having the following substituents on nitrogen: benzyl, 2-methoxybenzyl, 2-hydroxyethyl, allyl, 2-furylmethyl, and 2-pyridylmethyl.Isolated yields of pure product for the one-step reaction were in the range 26 +/- 4percent.The corresponding derivatives of 7 having 2-methoxyethyl, carbethoxymethyl, carboxymethyl, and 2-hydroxybenzyl sidearms were also prepared so that cation selectivity as a function of structure could be assessed.Homogeneous stability constants (Ks) for the association between the various ligands and Na+, K+, and Ca2+ were determined and are reported.Significant Ca2+ selectivity is achieved for the first time in these systems which should retain a high degree of binding dynamics since the donor groups of primary interest in this study are non-ionizable.
NOVEL SYNTHETIC ACCESS TO 15- AND 18-MEMBERED RING. DIAZA-BIBRACCHIAL LARIAT ETHERS (BiBLEs) AND A STUDY OF SIDEARM-MACRORING. COOPERATIVITY IN CATION BINDING
Gatto, Vincent J.,Arnold, Kristin A.,Viscariello, Anthony M.,Miller, Steven R.,Gokel, George W.
, p. 327 - 330 (2007/10/02)
An extremely practical synthesis of 4,10-diaza-15-crown-5, 4,13-diaza-18-crown-6, and symmetrically N,N'-disubstituted derivatives thereof, is presented along with the first survey of cation binding data for the 15-membered ring systems.
