Alkoxymethyl-substituted 18-crown-6 and 21-crown-7 ligands: Synthesis, complexation properties, and metal ion membrane separations

Chuan Wang, P. Huszthy, Jerald S. Bradshaw, John D. Lamb, Bogdan Olenyuk, David Bearss, Reed M. Izatt

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Three novel alkoxymethyl-substituted 18-crown-6 (8–10) and one new alkoxymethyl-substituted 21-crown-7 (11) ligands have been prepared. First, 1-0-tritylpropanetriol (1) and penta- or hexaethylene glycol ditosylate were cyclized in the presence of an alkali metal hydride. The resulting trityloxymethyl-substituted crowns were deprotected to give the hydroxymethyl-substituted 18-crown-6 (6) and hydroxymethyl-substituted 21-crown-7 (7). The latter compounds were alkylated using sodium hydride and the appropriate 1-bromoalkane to form 8–11. Complexation properties of these new ligands with the alkali metal cations were studied by a calorimetric titration technique. Compared with the parent 18-crown-6 and 21-crown-7 ligands, the substituted 18-crown-6 ligands demonstrate superior selectivity for K’, while the substituted 21-crown-7 ligand demonstrated less selectivity for Cs+over other alkali cations. Solvent extraction and membrane separation experiments using these new ligands were also carried out. The results demonstrated that the structural features of these new ligands have a significant influence on cation complexation selectivity and separations potential.

Original languageEnglish
Pages (from-to)1589-1607
Number of pages19
JournalSeparation Science and Technology
Volume30
Issue number7-9
DOIs
Publication statusPublished - 1995

Fingerprint

Complexation
Metal ions
Ligands
Membranes
Alkali Metals
Cations
Positive ions
Alkali metals
Hydrides
Alkalies
Solvent extraction
18-crown-6
Glycols
Titration
Sodium
Experiments

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Filtration and Separation
  • Process Chemistry and Technology
  • Chemistry(all)

Cite this

Alkoxymethyl-substituted 18-crown-6 and 21-crown-7 ligands : Synthesis, complexation properties, and metal ion membrane separations. / Wang, Chuan; Huszthy, P.; Bradshaw, Jerald S.; Lamb, John D.; Olenyuk, Bogdan; Bearss, David; Izatt, Reed M.

In: Separation Science and Technology, Vol. 30, No. 7-9, 1995, p. 1589-1607.

Research output: Contribution to journalArticle

Wang, Chuan ; Huszthy, P. ; Bradshaw, Jerald S. ; Lamb, John D. ; Olenyuk, Bogdan ; Bearss, David ; Izatt, Reed M. / Alkoxymethyl-substituted 18-crown-6 and 21-crown-7 ligands : Synthesis, complexation properties, and metal ion membrane separations. In: Separation Science and Technology. 1995 ; Vol. 30, No. 7-9. pp. 1589-1607.
@article{259f27f640e94997a2c540ac68f5a471,
title = "Alkoxymethyl-substituted 18-crown-6 and 21-crown-7 ligands: Synthesis, complexation properties, and metal ion membrane separations",
abstract = "Three novel alkoxymethyl-substituted 18-crown-6 (8–10) and one new alkoxymethyl-substituted 21-crown-7 (11) ligands have been prepared. First, 1-0-tritylpropanetriol (1) and penta- or hexaethylene glycol ditosylate were cyclized in the presence of an alkali metal hydride. The resulting trityloxymethyl-substituted crowns were deprotected to give the hydroxymethyl-substituted 18-crown-6 (6) and hydroxymethyl-substituted 21-crown-7 (7). The latter compounds were alkylated using sodium hydride and the appropriate 1-bromoalkane to form 8–11. Complexation properties of these new ligands with the alkali metal cations were studied by a calorimetric titration technique. Compared with the parent 18-crown-6 and 21-crown-7 ligands, the substituted 18-crown-6 ligands demonstrate superior selectivity for K’, while the substituted 21-crown-7 ligand demonstrated less selectivity for Cs+over other alkali cations. Solvent extraction and membrane separation experiments using these new ligands were also carried out. The results demonstrated that the structural features of these new ligands have a significant influence on cation complexation selectivity and separations potential.",
author = "Chuan Wang and P. Huszthy and Bradshaw, {Jerald S.} and Lamb, {John D.} and Bogdan Olenyuk and David Bearss and Izatt, {Reed M.}",
year = "1995",
doi = "10.1080/01496399508010364",
language = "English",
volume = "30",
pages = "1589--1607",
journal = "Separation Science and Technology",
issn = "0149-6395",
publisher = "Taylor and Francis Ltd.",
number = "7-9",

}

TY - JOUR

T1 - Alkoxymethyl-substituted 18-crown-6 and 21-crown-7 ligands

T2 - Synthesis, complexation properties, and metal ion membrane separations

AU - Wang, Chuan

AU - Huszthy, P.

AU - Bradshaw, Jerald S.

AU - Lamb, John D.

AU - Olenyuk, Bogdan

AU - Bearss, David

AU - Izatt, Reed M.

PY - 1995

Y1 - 1995

N2 - Three novel alkoxymethyl-substituted 18-crown-6 (8–10) and one new alkoxymethyl-substituted 21-crown-7 (11) ligands have been prepared. First, 1-0-tritylpropanetriol (1) and penta- or hexaethylene glycol ditosylate were cyclized in the presence of an alkali metal hydride. The resulting trityloxymethyl-substituted crowns were deprotected to give the hydroxymethyl-substituted 18-crown-6 (6) and hydroxymethyl-substituted 21-crown-7 (7). The latter compounds were alkylated using sodium hydride and the appropriate 1-bromoalkane to form 8–11. Complexation properties of these new ligands with the alkali metal cations were studied by a calorimetric titration technique. Compared with the parent 18-crown-6 and 21-crown-7 ligands, the substituted 18-crown-6 ligands demonstrate superior selectivity for K’, while the substituted 21-crown-7 ligand demonstrated less selectivity for Cs+over other alkali cations. Solvent extraction and membrane separation experiments using these new ligands were also carried out. The results demonstrated that the structural features of these new ligands have a significant influence on cation complexation selectivity and separations potential.

AB - Three novel alkoxymethyl-substituted 18-crown-6 (8–10) and one new alkoxymethyl-substituted 21-crown-7 (11) ligands have been prepared. First, 1-0-tritylpropanetriol (1) and penta- or hexaethylene glycol ditosylate were cyclized in the presence of an alkali metal hydride. The resulting trityloxymethyl-substituted crowns were deprotected to give the hydroxymethyl-substituted 18-crown-6 (6) and hydroxymethyl-substituted 21-crown-7 (7). The latter compounds were alkylated using sodium hydride and the appropriate 1-bromoalkane to form 8–11. Complexation properties of these new ligands with the alkali metal cations were studied by a calorimetric titration technique. Compared with the parent 18-crown-6 and 21-crown-7 ligands, the substituted 18-crown-6 ligands demonstrate superior selectivity for K’, while the substituted 21-crown-7 ligand demonstrated less selectivity for Cs+over other alkali cations. Solvent extraction and membrane separation experiments using these new ligands were also carried out. The results demonstrated that the structural features of these new ligands have a significant influence on cation complexation selectivity and separations potential.

UR - http://www.scopus.com/inward/record.url?scp=0010413588&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0010413588&partnerID=8YFLogxK

U2 - 10.1080/01496399508010364

DO - 10.1080/01496399508010364

M3 - Article

AN - SCOPUS:0010413588

VL - 30

SP - 1589

EP - 1607

JO - Separation Science and Technology

JF - Separation Science and Technology

SN - 0149-6395

IS - 7-9

ER -