- Solubilities of diglycolic acid esters in supercritical carbon dioxide
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A series of new CO2-soluble diglycolic acid esters were designed and synthesized, and their structures were confirmed by IR, NMR, and elemental analysis. The solubilities of compounds were measured at temperatures ranging from (313 to 333) K and pressures from (8.5 to 19.3) MPa in supercritical carbon dioxide. AU of the newly synthesized esters showed good to high solubility (as high as 1.25 mol % for compound 1) in supercritical CO2 at easily accessible temperatures and pressures. The measured solubility data were correlated using a semiempirical model. Consequently, the calculated results showed satisfactory agreement with the experimental data and differed from the measured values by between (3.18 and 19.58) %.
- Xie, Yaoping,Yang, Hai-Jian,Wang, Wei,Chen, Rong
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- Bivalent ligand approach on 4-[2-(3-methoxyphenyl)ethyl]-1-(2-methoxyphenyl)piperazine: Synthesis and binding affinities for 5-HT7 and 5-HT1A receptors
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We here report on the synthesis and binding properties at 5-HT7 and 5-HT1A receptors of ligands 3-12, that were designed according to the 'bivalent ligand' approach. Two moieties of the 5-HT7/5-HT1A ligand 4-[2-(3-methoxyphenyl)ethyl]-1-(2-methoxyphenyl)piperazine (1) were linked through their 3-methoxy substituent by polymethylene chains of variable length, with the aim to increase the affinity for 5-HT7 receptor and the selectivity over 5-HT1A receptors. In the best cases, the dimers showed affinities for 5-HT7 receptors as high as the monomer with no improvement in selectivity. Some dimers displayed 5-HT1A receptor affinities slightly higher than monomer 1.
- Leopoldo, Marcello,Lacivita, Enza,Colabufo, Nicola A.,Niso, Mauro,Berardi, Francesco,Perrone, Roberto
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- Host-Guest Complexation. 38. Cryptahemispherands and Their Complexes
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Syntheses and crystal structures are reported for a new class of hosts, their complexes, and their precursors.The cryptahemispherands 5-8 are composed of molecular modules that are half spherand 1 and half cryptand 3.They were synthesized by the reactions of diacid chloride 20 with cyclic diamines 21-23 to produce diamides 13-16, reduction of which gave the desired hosts 5-8.These diamines were best purified, stored, and handled through their respective hydroborane complexes, 9-12.Hosts 6 and 7 are diastereomeric, as are diamides 14 and 15 and hydroborane complexes 10 and 11.Diamines 6 and 7 equilibrate rapidly at 25 deg C probably by ring inversion of the methoxyl groups to give a 5:1 ratio of 6 over 7.Diamides 14 and 15 equilibrate readily at 90 deg C to give only 14 in detectable amounts.Hydroborane complexes 10 and 11 do not equilibrate at 90 deg C.Cryptahemispherands 5, 6 and 8 formed a variety of complexes with the alkali metal cations, diamides 14 and 16 exhibited a low level of binding power, and hydroborane complexes 10 and 12 had no detectable affinity for the alkali metal cations.Hemispherand 17 was synthesized for comparison purposes.Crystal structures were determined for the isomeric diamides 14 and 15, for hydroborane complex 9, and for alkali cation complexes 5.NaB(Ph)4, 6.KSCN, 8.NaSCN, 8.KSCN, and 8.CsClO4.The trisanisyl modules of all eight compounds possess the same preorganized conformation, with the unshared electron pairs of the three methoxyl groups turned inward and the methyl groups outward.The potential cavities of 9, 14, and 15 are filled inward-turned hydrogens of the ethylene bridges.In the alkali metal ion complexes, the unshared electron pairs of the heteroatoms are all turned inward toward the quest metal ion.The use of CPK molecular models in predicting the structures of complexes is evaluated.
- Cram, Donald J.,Ho, Siew Peng,Knobler, Carolyn B.,Maverick, Emily,Trueblood, Kenneth N.
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- Synthesis, Characterization, and Preclinical Evaluation of 99mTc-Labeled Macrobicyclic and Tricyclic Chelators as Single Photon Emission Computed Tomography Tracer
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The novel tetraaza macrobicyclic chelator 3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene-2,10-dione (TBPD) and pentaaza macrotricyclic chelator 9-oxa-3,6,12,15,21-pentaazatricyclo[15,3,2,1]trieicos-1(21),17,19-triene-2,7,11,16-tetradione (OPTT) were synthesized, characterized, and radiolabeled with 99mTc to produce 99mTc-TBPD and 99mTc-OPTT. These radiolabeled complexes were prepared with high radiolabeling yield, radiochemical purity, and good in vitro stability up to 24 h. The labeling efficiency of 99mTc-TBPD and 99mTc-OPTT was found 98% and 97%. In vitro serum stability of 99mTc-TBPD was found to be 95.2%, while that of 99mTc-OPTT 94.2% up to 24 h. Blood kinetics experiments of 99mTc-labeled complexes showed biphasic pattern of blood clearance. About 99.57 ± 0.89% activity of 99mTc-TBPD and 99.42 ± 0.88% activity of 9mTc-OPTT were cleared off blood stream at 24 h postadministration. The biological half-life of 99mTc-TBPD was observed: t1/2(F) 1 h 5 min and t1/2(S) 12 h and biological half-life of 99mTc-OPTT was observed: t1/2(F) 1 h 10 min and t1/2(S) 9 h 50 min, respectively. The biodistribution studies revealed that maximum uptake of 99mTc-TBPD was found in liver, concluded that excretory pathway is hepatobiliary, while that of 99mTc-OPTT was renal as well as hepatobiliary. The negligible activity observed in stomach confirming the stability of radiolabeled complex in biological milieu. In vitro cytotoxicity study of TBPD and OPTT did not show any considerable antiproliferative activity against cancer cells of human cervical SW756, HeLa, and glioblastoma U-87, U373 cell lines.
- Yadav, Neelam,Chuttani, Krishna,Mishra, Anil K.,Singh, Bachcha
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- Solubilities of amide compounds in supercritical carbon dioxide
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2,2′-Oxybis(N,N-diethylacetamide), 2,2′-oxybis(N,N- dibutylacetamide), and 2,2′-oxybis(N,N-dihexylacetamide) were synthesized, and their structures were confirmed by IR, NMR, and elemental analysis. The solubilities of compounds were measured at temperatures ranging from (313 to 333) K and pressures from (8.7 to 16.4) MPa in supercritical carbon dioxide. The measured solubilities were correlated using a semiempirical model. The calculated results showed satisfactory agreement with the experimental data and differed from the measured values by between (4.54 and 30.84) %.
- Liu, Jiang-Fan,Yang, Hai-Jian,Wang, Wei,Li, Zhongxiao
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- Secondary amine containing ether bond, amido podand ligand, as well as preparation method and application thereof
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The invention discloses an secondary amine containing ether bond, an amido podand ligand, as well as a preparation method and application thereof, wherein the secondary amine containing ether bond hasa structural general formula as shown in the specification, contains ether bonds, has higher flexibility than pure carbon chain secondary amine, and is easy to prolong the number of atoms; Therefore,candidate secondary amines with excellent performance are provided for the fields of organic synthetic chemistry and medicinal chemistry. The amido podand ligand prepared by taking secondary amine asa raw material is used as an extraction agent of a lanthanide/actinide co-extraction system in spent fuel post-treatment, and can effectively inhibit the formation of three phases under higher metalion concentration or nitric acid concentration, so that a good separation effect is achieved in an acidity range of industrial application; therefore, the amido podand not only has strong practicability, but also has a good application prospect in the field of advanced nuclear fuel circulation.
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Paragraph 0146-0150; 0155-0159; 0163-0167; 0171-0175;
(2020/11/23)
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- Novel process for synthesizing N,N,N',N'-tetraoctyl-3-oxyglutaramide
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The invention provides a novel process for synthesizing N,N,N',N'-tetraoctyl-3-oxyglutaramide (TODGA). The novel process includes the steps of firstly, allowing diglycolic acid to have reaction with SOCl2 to generate diglycolic acyl chloride, and allowing the diglycolic acyl chloride to have reaction with amine to generate part of TODGA; secondly, removing components, which can be easily dissolvedin water, in the byproducts, and separating to obtain monooxaamide carboxylic acid; thirdly, allowing the monooxaamide carboxylic acid to have reaction with amine to generate part of TODGA again. Bythe novel process with the features of an existing process, high yield is achieved.
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Paragraph 0026; 0027; 0030; 0031; 0034; 0035
(2019/07/04)
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- CYCLIC PEPTIDES MULTIMERS TARGETING α4β7 INTEGRIN
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There is described herein, multimers comprising a plurality of compounds covalently linked together, the compounds independently being of formula (I).
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Page/Page column 29; 30
(2018/05/27)
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- Selective recovery of rare earth elements using chelating ligands grafted on mesoporous surfaces
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Nowadays, rare earth elements (REEs) and their compounds are critical for the rapidly growing advanced technology sectors and clean energy demands. However, their separation and purification still remain challenging. Among different extracting agents used for REE separation, the diglycolamide (DGA)-based materials have attracted increasing attention as one of the most effective extracting agents. In this contribution, a series of new and element-selective sorbents were generated through derivatisation of the diglycolamide ligand (DGA), grafted to mesoporous silica and tested for the separation of rare earth elements. It is shown that, by tuning the ligand bite angle and its environment, it is possible to improve the selectivity towards specific rare earth elements.
- Florek, Justyna,Mushtaq, Ambreen,Larivière, Dominic,Cantin, Gabrielle,Fontaine, Frédéric-Georges,Kleitz, Freddy
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p. 103782 - 103789
(2015/12/24)
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- 99mTc labeled macrocyclic aza-oxa and aza-thia probes: Synthesis, characterization and in vitro & in vivo biological studies
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Macrocyclic chelating agents 1-oxa-4,7,10-triazacyclopentadecane-3,11-dione (OTDD) and 1-thia-4,7, 10-triazacyclododecane-3,11-dione (TTDD) have been synthesized and labeled with radionuclide (99mTc), with radiolabeling efficiency 97.6 and 98.4 % respectively. The radiochemical purity of labeled complex (99mTc-OTDD and 99mTc-TTDD) was determined 97.5 and 98.1 %, respectively. The in vitro stability of the labeled chelates in human serum exhibited only 99mTc-TTDD is hepatobilliary and minor is renal, while in case of 99mTc-OTDD hepatobilliary as well as renal both comparable. The in vivo blood kinetic studies of radio-complexes of 99mTc-OTDD and 99mTc-TTDD showed 99.26 and 99.4 % blood clearance over 24 h post injection. The biological half-life of 99mTc-OTDD and 99mTc-TTDD with t1/2(F) 1 h 10 min, t1/2(S) 18 h 50 min and t1/2(F) 1 h 42 min, t1/2(S) 18 h 20 min respectively. In vitro cytotoxicity study of OTDD and TTDD did not exhibit any significant antiproliferative property against cancer cells of human glioblastoma U-87, U373 and cervical SW756, HeLa cell lines.
- Yadav, Neelam,Chuttani, Krishna,Mishra, Anil K.,Singh, Bachcha
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p. 299 - 307
(2016/02/27)
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- HYDROLYSABLE LINKERS AND CROSS-LINKERS FOR ABSORBABLE POLYMERS
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The present invention relates to the discovery of new class of linear and multiarmed hydrolysable linkers and cross linkers for use in the synthesis of biodegradable polymers such as, polyesters, polyurethanes, polyamides, polyureas and degradable epoxy amine resin. The linear and multiarmed hydrolysable linkers of the present invention include symmetrical and/or unsymmetrical ether carboxylic acids, amines, amide diols, amine polyols and isocyanates.
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Page/Page column 37
(2012/08/08)
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- CYTOSOLIC FLUORESCENT ION INDICATORS
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Novel fluorophores for fluorescent ion indicators incorporate water-solubilizing functional groups. These fluorophores enable visible-wavelength analysis of ion concentrations with chelators that are insoluble or poorly soluble in water. A green version of the fluorophore comprises a putative fluorescein with carboxylate appendages. An orange version of the fluorophore comprises a putative rhodamine, also with carboxylate appendages. Attaching the fluorophore to a 12-crown-4, a 15-crown-5, a 18-crown-6, a 21-crown-7, or a 24-crown-8 produces lithium, sodium, potassium, rubidium, and cesium indicator families, respectively. Attaching the fluorophore to diaza [1,1,1], [1,1,2], [1,2,2], [2,2,2], [2,2,3], [2,3,3], or [3,3,3] cryptands produces more selective lithium, sodium, potassium, rubidium, and cesium indicator families, respectively. Attaching the fluorophore to BAPTA, APTRA, or half- BAPTA or their analogs produces new calcium, magnesium, and other metal ions indicator families that strongly resist leakage from the cell.
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Page/Page column 27
(2012/04/10)
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- Functionalized biodegradable triclosan monomers and oligomers for controlled release
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This invention relates to the discovery of functionalized triclosan monomers and oligomers that, when incorporated into a substrate of, or applied as part of a coating to, medical devices and/or consumer products may extend the duration of antimicrobial properties to the medical devices and/or consumer products.
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Page/Page column 62
(2011/11/13)
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- FUNCTIONALIZED BIODEGRADABLE TRICLOSAN MONOMERS AND OLIGOMERS FOR CONTROLLED RELEASE
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This invention relates to the discovery of functionalized triclosan monomers and oligomers that, when incorporated into a substrate of, or applied as part of a coating to, medical devices and/or consumer products may extend the duration of antimicrobial properties to the medical devices and/or consumer products.
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- Synthesis of new macrocyclic lactones and their extraction study
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New macrocyclic lactones were synthesized by reaction of 3-bromo-5-(5-tert-butyl-2-hydroxybenzyl)biphenyl-4-ol with appropriate polyethylene glycol-based dicarboxylic acid dichlorides, and their complexes with Mg(ClO4)2·6H2O, Pb(SCN) 2, NaClO4·H2O, and KClO4 were prepared. The macrocyclic ligands were evaluated as extractants in the transfer of Li+, Na+, K+, Cu2+, Ni 2+, and Hg2+ picrates from aqueous to organic phase.
- Bayrakci,Ertul
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experimental part
p. 1384 - 1388
(2009/09/06)
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- Condensation of Diglycolic Acid Dichloride with Polyglycols. 5. An Improved Synthesis of Cyclic Polyether-Esters by Cyclization
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An improved synthesis of oligocyclic (ether-ester)s by cyclization condensation of polyglycols with diglycolic acid dichloride in benzene/pyridine or dioxane/pyridine is reported. Keywords: Macrocyclic oligo(ether-ester)s
- Erk, Cakil
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p. 1083 - 1084
(2007/10/02)
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- Preparation of Ca(2+) Selective Sorbents by Molecular Imprinting using Polymerisable Ionophores
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Molecular imprints against calcium and magnesium ions, respectively, were prepared in divinylbenzene-based polymers.A vinylic, Ca2+-selective, neutral ionophore N,N'-dimethyl-N,N'-bis-(4-vinylphenyl)-3-oxapentanediamide was synthesized and used as the ion-complexing monomer.In order to investigate the ion-complexing abilities of this neutral ionophore, this compound was tested as a neutral carrier in the plasticised PVC membrane of an ion-selective electrode.Electrode response and selectivity coefficients recorded for the ionophore proved to be equivalent to the values recorded for similar parent diglycolic acid amides.In analogy with other 3-oxapentanediamide derivatives, the ionophore is expected to form complexes with calcium and magnesium ions with a molar ratio, ligand to metal ion, of 3:1 and 2:1, respectively.Therefore the metal ion, added to the polymerisation mixture, was expected to act as a template for the ionophore during the polymerisation.The resulting polymers were analysed for their ability to extract calcium ions from methanolic water.The polymers prepared against calcium and magnesium ions were found to bind calcium ions with 6- and 1.7-times lower Kdiss-values, respectively, when compared with reference polymers prepared in the absence of metal ions. The increased binding strength is attributed to the spatial arrangement of ionophore units in the resulting polymers by the template ions during the polymerisation.In addition, the number of binding sites for calcium ions, determined for the respective polymer preparation, fitted well with theoretical values calculated from the stoichiometry of complexation of the ionophore by calcium and magnesium ions, respectively.
- Rosatzin, Thomas,Andersson, Lars I.,Simon, Wilhelm,Mosbach, Klaus
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p. 1261 - 1266
(2007/10/02)
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- Transition-state stabilization and molecular recognition: Acceleration of phosphoryl-transfer reactions by an artificial receptor
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An artificial receptor that is complementary to the proposed trigonal-bipyramidal intermediate for phosphoryl-transfer reactions has been designed. Kinetic measurements with 31P NMR methods show that the receptor causes up to a 10-fold acceleration in the aminolysis of phosphorodiamidic chloride derivatives, proceeding via an associative mechanism.
- Tecilla, Paolo,Chang, Suk-Kyu,Hamilton, Andrew D.
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p. 9586 - 9590
(2007/10/02)
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- A BARIUM SELECTIVE MACROCYCLIC TETRALACTAM WITH DIMETHYLENEOXY MOIETIES
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Two new 18-membered tetralactams with two dimethyleneoxy moieties are synthesized by direct macrocyclization or steps reaction.In the latter case symmetrical or unsymmetrical compounds can be obtained.The unsymmetrical tetralactam shows a very high selectivity for barium vs.Na+ and Zn2+ and to a lesser extent vs.K+, Mg2+ and Ca2+ in the extraction procedure with picrates.In addition, the stability constants are determined for the two 1:1 tetralactam:Ba2+ complexes by UV spectrophotometry in THF solution.
- Cazaux, Louis,Duriez, Marie-Christine,Picard, Claude,Tisnes, Pierre
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p. 1369 - 1372
(2007/10/02)
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- CHIRAL AMINOACID CONTAINING ACYCLIC LIGANDS-I. SYNTHESES AND CONFORMATIONS
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Synthesis and spectral properties of optically active acyclic ligands, containing two (S)-phenylalanine residues (3a-f) are described.The synthesis is achieved by two different routes.Conformational studies in different solvents are performed by dilution and temperature-dependent experiments of 1H and 13C NMR spectroscopy.
- Lodi, T.,Marchelli, R.,Dossena, A.,Dradi, E.,Casnati, G.
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p. 2055 - 2060
(2007/10/02)
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- Synthesis and Characterization of Some Bifunctional 2B:2:1 Cryptands
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Methods for the synthesis of aromatic substituted diaza-polyoxamacrobicyclic compounds (benzocryptands) are described.New synthetic routes to cryptand precursors are developed and improvements in cryptand synthesis discussed and employed to prepare some bifunctional cryptands.
- Gansow, Otto A.,Kausar, A. Rashid,Triplett, Kelly B.
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p. 297 - 302
(2007/10/02)
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- 16. Ionophore vom Typ der 3-Oxapentadiamide
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A series of lipophilic 3-oxapentane diamides were prepared and their selectivity in membranes was studied.N,N,N',N'-Tetracyclohexyl-3-oxapentane diamide forms 1:2- and 1:3-metal/ligand-complexes with Mg(2+) and Ca(2+) respectively and induces a selectivity in membranes for Ca(2+) over Mg(2+) by a factor of about 10E4.
- Pretsch, Erno,Ammann, Daniel,Osswald, Hans F.,Guggi, Marc,Simon, Wilhelm
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p. 191 - 196
(2007/10/02)
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- Complexes of macrocyclic compounds
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Novel macrocyclic (monocyclic and bicyclic) compounds having nitrogen bridgehead atoms and having in the hydrocarbon bridging chains at least two additional hetero atoms selected from the group consisting of sulfur, oxygen, and nitrogen, when admixed with a compatible cation-donor compound form stable cation-containing macrocyclic complexes which, in turn, can be conveniently dissociated by addition of acid or a quaternizing agent. The novel macrocyclics are valuable for use in the same way and for the same purposes as chelating agents.
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