Rational Design of Cesium-Selective Ionophores: Dihydrocalix[4]arene Crown-6 Ethers

Richard A. Sachleben; Jeffrey C. Bryan; Nancy L. Engle; Tamara J. Haverlock; Benjamin P. Hay; Agathe Urvoas; Bruce A. Moyer

doi:10.1002/ejoc.200300002

Rational Design of Cesium-Selective Ionophores: Dihydrocalix[4]arene Crown-6 Ethers

Richard A. Sachleben
, Jeffrey C. Bryan
, Nancy L. Engle
, Tamara J. Haverlock
, Benjamin P. Hay
, Agathe Urvoas
, Bruce A. Moyer

Research output: Contribution to journal › Article › peer-review

21 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	4862-4869
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	24
DOIs	https://doi.org/10.1002/ejoc.200300002
State	Published - Dec 15 2003

Keywords

Alkali metals
Calixarenes
Liquid-liquid extraction
Molecular modeling

Access to Document

10.1002/ejoc.200300002

Cite this

@article{d43d734aa17b429b8b899e605c99cbc2,

title = "Rational Design of Cesium-Selective Ionophores: Dihydrocalix[4]arene Crown-6 Ethers",

abstract = "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.",

keywords = "Alkali metals, Calixarenes, Liquid-liquid extraction, Molecular modeling",

author = "Sachleben, \{Richard A.\} and Bryan, \{Jeffrey C.\} and Engle, \{Nancy L.\} and Haverlock, \{Tamara J.\} and Hay, \{Benjamin P.\} and Agathe Urvoas and Moyer, \{Bruce A.\}",

year = "2003",

month = dec,

day = "15",

doi = "10.1002/ejoc.200300002",

language = "English",

pages = "4862--4869",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "wiley",

number = "24",

}

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 - https://www.scopus.com/pages/publications/0346732145

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 -

Rational Design of Cesium-Selective Ionophores: Dihydrocalix[4]arene Crown-6 Ethers

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this