TY - JOUR
T1 - Rational Design of Cesium-Selective Ionophores
T2 - Dihydrocalix[4]arene Crown-6 Ethers
AU - Sachleben, Richard A.
AU - Bryan, Jeffrey C.
AU - Engle, Nancy L.
AU - Haverlock, Tamara J.
AU - Hay, Benjamin P.
AU - Urvoas, Agathe
AU - Moyer, Bruce A.
PY - 2003/12/15
Y1 - 2003/12/15
N2 - Molecular mechanics calculations performed on calix[4]-arene crown-6 ethers predict that the 1,3-dihydro derivatives will exhibit greater complementarity for potassium and cesium ions than the parent 1,3-bis(alkyloxy) calixcrowns. The X-ray crystal structures of 1,3-alt-bis(octyloxy)calix[4]arene benzocrown-6 ether, dihydrocalix[4]arene benzocrown-6 ether, and the cesium nitrate complex of dihydrocalix[4]-arene benzocrown-6 ether were determined. The structure of the cesium complex corresponds closely to the structure predicted by molecular mechanics. The dihydrocalix[4]arene crown-6 ethers exhibit enhanced cesium selectivity in the extraction of alkali-metal salts.
AB - Molecular mechanics calculations performed on calix[4]-arene crown-6 ethers predict that the 1,3-dihydro derivatives will exhibit greater complementarity for potassium and cesium ions than the parent 1,3-bis(alkyloxy) calixcrowns. The X-ray crystal structures of 1,3-alt-bis(octyloxy)calix[4]arene benzocrown-6 ether, dihydrocalix[4]arene benzocrown-6 ether, and the cesium nitrate complex of dihydrocalix[4]-arene benzocrown-6 ether were determined. The structure of the cesium complex corresponds closely to the structure predicted by molecular mechanics. The dihydrocalix[4]arene crown-6 ethers exhibit enhanced cesium selectivity in the extraction of alkali-metal salts.
KW - Alkali metals
KW - Calixarenes
KW - Liquid-liquid extraction
KW - Molecular modeling
UR - http://www.scopus.com/inward/record.url?scp=0346732145&partnerID=8YFLogxK
U2 - 10.1002/ejoc.200300002
DO - 10.1002/ejoc.200300002
M3 - Article
AN - SCOPUS:0346732145
SN - 1434-193X
SP - 4862
EP - 4869
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 24
ER -