Synthesis and acidity of crown ethers with pendant carboxylic acid groups

Bartsch, Richard A.; Heo, Gwi Suk; Kang, Sang Ihn; Liu, Yung; Strzelbicki, Jerzy

doi:10.1021/jo00342a016

Cited by 96 publications

(52 citation statements)

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“…Therefore, methyl esters were favored over ethyl esters in this synthetic route. The preparation of lariat ether carboxylic acid 68 was reported previously [7] by another method, but in low overall yield.…”

Section: Compared With Sym-(r)dibenzo-16-crown-5-oxyaceticmentioning

confidence: 97%

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Synthesis of lariat ether carboxylic acids based on dibenzo‐16‐crown‐5

Bartsch

Cowey

Elshani

et al. 2001

Journal of Heterocyclic Chem

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Synthetic routes to forty‐seven dibenzo‐16‐crown‐5 compounds with pendant carboxylic acid groups are reported. When taken together with previously described lariat ether carboxylic acids, these new compounds provide several series with systematic structural variations including changes in the identity and attachment site(s) of one or more lipophilic groups and the length of the spacer that connects the carboxylic acid group to the polyether framework.

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Section: Compared With Sym-(r)dibenzo-16-crown-5-oxyaceticmentioning

confidence: 97%

“…Previously we have described the preparation of several dibenzo-16-crown-5 carboxylic acids [7,9,11,13,14,19,26,[32][33][34]. However, these compounds provide only limited structural variation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of lariat ether carboxylic acids based on dibenzo‐16‐crown‐5

Bartsch

Cowey

Elshani

et al. 2001

Journal of Heterocyclic Chem

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“…The overall preparation of the fullerene(C60)-crown ether coating material, C60-sym-dibenzo-16-crown-5-oxyacetic acid (DB16C5-OCH 2 -COOC 60 ), is depicted in Fig 1. The syn thetic procedure of sym-dibenzo-16-crown-5-oxyacetic acid was the same as previously reported 26 …”

Section: Experimental Preparation Of Fullerene-crown Ether Coating Mamentioning

confidence: 99%

Fullerene‐Crown Ether Coated Piezoelectric Crystal Liquid Chromatographic Detector for Metal Ions and Polar/Nonpolar Organic Molecules

Hung¹,

Shih²

2000

J Chinese Chemical Soc

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Fullerene(C60)-dibenzo-16-crown-5-oxyacetic acid (DBI6C5-OCH2-COOC60) was prepared and applied as the coating material on piezoelectric quartz crystals for detection of various metal ions and polar/nonpolar organic molecules. The C60-crown ether-coated piezoelectric crystal sensor with a home-made computer inter face for signal acquisition and data processing was applied as an ion Chromatographie (IC) detector for various metal ions, e.g., alkali metal, alkaline earth metal and transition-metal ions. The piezoelectric detector exhib ited quite good sensitivity of 10 4 ~ 10 6 Hz/M and good detection limit of 10" 3 ~ 10" 4 M for these metal ions. The C60-crown ether piezoelectric detector compared well with the commercial conductivity detector convention ally used for metal ions. The ionic size and ionic charge seemed to have significant effect on the frequency re sponse of the piezoelectric detector. The C60-crown ether coated piezoelectric crystal sensor was also em ployed as a high performance liquid Chromatographie (HPLC) detector for various polar organic molecules with frequency responses in the order: amines > carboxylic acids > alcohols > ketones. Furthermore, nonpolar organic molecules, e.g., n-hexane, 1-hexene and 1-hexyne, were also detected with this piezoelectric crystal de tector. The frequency responses of the piezoelectric crystal detector for these nonpolar organic molecules were in the following order: alkynes » alkenes > alkanes. The effects of solvents and flow rate on the frequency re sponses of the piezoelectric crystal detector were investigated. The C60-crown ether coated piezoelectric crys tal detector also showed short response time (< 1 min.) and good reproducibility.

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“…In earlier work, we prepared lariat ether derivatives based upon a dibenzo-16-crown-5 scaffold in which oxyacetic acid [3][4][5][6][7][8], oxyacetohydroxamic acid [7], monoethyl oxymethylphosphonic ester [9], or N-(X)sulfonyl oxyacetamide groups [10] were attached to the central carbon of the three-carbon bridge in the polyether ring. In their ionized forms, such proton-ionizable lariat ethers are efficient and selective agents for the solvent extraction of alkali metal, alkaline earth metal, and lanthanide ions and for their transport across liquid membranes [7,[9][10][11][12][13][14][15][16][17][18][19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of dibenzo‐16‐crown‐5 compounds with pendant ester and ether groups

Babb¹,

Bartsch²,

Collier³

et al. 2004

Journal of Heterocyclic Chem

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Structurally related dibenzo-16-crown-5 lariat ethers with pendant ester and ether groups are prepared. Structural variations within the series of alkyl lariat ether esters include changes in the O-alkyl group, attachment site and nature of the lipophilic group, and length of the spacer, which connects the ester group to the polyether framework. Also synthesized are bis(crown ether) diesters with two dibenzo-16-crown-5 or two dicyclohexano-16-crown-5 units and two ester groups connected to each other by a linker of varying length. Synthetic strategies for the preparation of these lariat ethers with pendant ester-and ether-containing side arms are described.

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Synthesis and acidity of crown ethers with pendant carboxylic acid groups

Cited by 96 publications

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Synthesis of lariat ether carboxylic acids based on dibenzo‐16‐crown‐5

Synthesis of lariat ether carboxylic acids based on dibenzo‐16‐crown‐5

Fullerene‐Crown Ether Coated Piezoelectric Crystal Liquid Chromatographic Detector for Metal Ions and Polar/Nonpolar Organic Molecules

Synthesis of dibenzo‐16‐crown‐5 compounds with pendant ester and ether groups

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