Anion binding in aqueous media by a tetra-triazolium macrocycle

Nicholas G. White; Sílvia Carvalho; Vítor Félix; Paul D. Beer

doi:10.1039/c2ob25934f

Anion binding in aqueous media by a tetra-triazolium macrocycle

Nicholas G. White, Sílvia Carvalho, Vítor Félix, Paul D. Beer^*

^*Corresponding author for this work

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

42 Citations (Scopus)

Abstract

Three tetra-triazole macrocycles were synthesized in good yields by the copper(i)-catalysed cycloaddition of bis-triazole azides and bis-alkynes. One of these was alkylated to give a cyclic tetra-triazolium receptor, which complexes anions strongly in competitive DMSO-water mixtures. In 1:1 DMSO-water, the tetracationic receptor exhibits a preference for the larger halides, bromide and iodide, with all halides associating more strongly than the oxoanion, acetate. The sulfate dianion is complexed far more strongly than any of the monobasic anions (K _a > 10 ⁴ M ^-1). Quantum mechanics/molecular mechanics simulations corroborate the experimentally determined anion binding selectivity trends.

Original language	English
Pages (from-to)	6951-6959
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	34
DOIs	https://doi.org/10.1039/c2ob25934f
Publication status	Published - 14 Sept 2012
Externally published	Yes

Access to Document

10.1039/c2ob25934f

Cite this

@article{9f644901d7c54c429f7c9f4bb15568cb,

title = "Anion binding in aqueous media by a tetra-triazolium macrocycle",

abstract = "Three tetra-triazole macrocycles were synthesized in good yields by the copper(i)-catalysed cycloaddition of bis-triazole azides and bis-alkynes. One of these was alkylated to give a cyclic tetra-triazolium receptor, which complexes anions strongly in competitive DMSO-water mixtures. In 1:1 DMSO-water, the tetracationic receptor exhibits a preference for the larger halides, bromide and iodide, with all halides associating more strongly than the oxoanion, acetate. The sulfate dianion is complexed far more strongly than any of the monobasic anions (K a > 10 4 M -1). Quantum mechanics/molecular mechanics simulations corroborate the experimentally determined anion binding selectivity trends.",

author = "White, {Nicholas G.} and S{\'i}lvia Carvalho and V{\'i}tor F{\'e}lix and Beer, {Paul D.}",

year = "2012",

month = sep,

day = "14",

doi = "10.1039/c2ob25934f",

language = "English",

volume = "10",

pages = "6951--6959",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "34",

}

TY - JOUR

T1 - Anion binding in aqueous media by a tetra-triazolium macrocycle

AU - White, Nicholas G.

AU - Carvalho, Sílvia

AU - Félix, Vítor

AU - Beer, Paul D.

PY - 2012/9/14

Y1 - 2012/9/14

N2 - Three tetra-triazole macrocycles were synthesized in good yields by the copper(i)-catalysed cycloaddition of bis-triazole azides and bis-alkynes. One of these was alkylated to give a cyclic tetra-triazolium receptor, which complexes anions strongly in competitive DMSO-water mixtures. In 1:1 DMSO-water, the tetracationic receptor exhibits a preference for the larger halides, bromide and iodide, with all halides associating more strongly than the oxoanion, acetate. The sulfate dianion is complexed far more strongly than any of the monobasic anions (K a > 10 4 M -1). Quantum mechanics/molecular mechanics simulations corroborate the experimentally determined anion binding selectivity trends.

AB - Three tetra-triazole macrocycles were synthesized in good yields by the copper(i)-catalysed cycloaddition of bis-triazole azides and bis-alkynes. One of these was alkylated to give a cyclic tetra-triazolium receptor, which complexes anions strongly in competitive DMSO-water mixtures. In 1:1 DMSO-water, the tetracationic receptor exhibits a preference for the larger halides, bromide and iodide, with all halides associating more strongly than the oxoanion, acetate. The sulfate dianion is complexed far more strongly than any of the monobasic anions (K a > 10 4 M -1). Quantum mechanics/molecular mechanics simulations corroborate the experimentally determined anion binding selectivity trends.

UR - http://www.scopus.com/inward/record.url?scp=84865008494&partnerID=8YFLogxK

U2 - 10.1039/c2ob25934f

DO - 10.1039/c2ob25934f

M3 - Article

SN - 1477-0520

VL - 10

SP - 6951

EP - 6959

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 34

ER -

Anion binding in aqueous media by a tetra-triazolium macrocycle

Abstract

Access to Document

Other files and links

Fingerprint

Cite this