Structure–alkali metal cation complexation relationships for macrocyclic PNP-lariat ether ligandsElectronic supplementary information (ESI) available: diagnostic 31P NMR and 1H NMR spectral data and combustion analyses for new PNP-lariat and bis-lariat ethers. See http://www.rsc.org/suppdata/p2/b1/b110415b/

Bartsch, Richard A.; Lee, Eun Kyung; Chun, Sangki; Elkarim, Nazar S. A.; Brandt, K.; Porwolik-Czomperlik, Iwona; Siwy, Mariola; Lach, Dariusz; Silberring, Jerzy

doi:10.1039/b110415b

Cited by 20 publications

(7 citation statements)

References 27 publications

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“…18 This type of lariat ethers may be regarded as "intelligent substrate" because it possesses reactive sites capable for spontaneous self assembling with molecular complementary reagents. This compound has the reactive chloride substituents, capable of undergoing various substitution reaction, in particular with sodium arylates [19][20][21] and different amines. [22][23][24] Due to the presence of binding sites in the form of both oxygen and nitrogen donor atoms, these ligands form stable complexes with cations of alkali metals and alkaline earth metals as well as transition metals.…”

Section: Introductionmentioning

confidence: 99%

Doubly-bridged PNP-lariat ethers and their complexes with silver(i) ions in methanol solution

et al. 2013

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We report the preparation of four new double-bridged PNP-lariat ether derivatives L1-L4 synthesized from precursor 1 by the subsequent substitution of chlorine atoms. The process consists of two steps. In the first one two reactive chlorine atoms of the -PCl 2 exocyclic moiety are substituted with respective nucleophiles: 2,2 0 -thiodiethanethiol 2 and 2,2 0 -oxydiethanethiol 3. In the second step the other chlorine atoms are substituted by aziridynyl 6 and pyrrolidinyl 7 groups, respectively. Their structures were established by MS, 1 H NMR, 31 P NMR, 13 C NMR spectroscopy. Furthermore, this work includes the investigation of complexation of silver(I) ions with the new ligands L1-L4 in methanol solution. The formation of the novel tetra-nuclear silver(I) complexes were observed. Stability constants were determined using a simple potentiometric titration. 1 H NMR, 31 P NMR, 13 C NMR spectra were recorded to investigate how the complexation of silver(I) ions by the investigated macrocyclic ligands occurs.Scheme 1 Polymacrocyclic structures formed in the reaction of chlorocyclophosphazenes with diamines.

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Section: Introductionmentioning

confidence: 99%

Doubly-bridged PNP-lariat ethers and their complexes with silver(i) ions in methanol solution

et al. 2013

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“…There are known PNP-lariat ethers substituted with different amines [12][13][14][15][16] and sodium arylates. 17,18 In this work we present two derivatives of PNP-lariat ethers.…”

Section: Introductionmentioning

confidence: 99%

Complexes of silver(i) ions with tetrapyrrolidinyl- and tetramorpholinyl-PNP-lariat ethers in acetonitrile and methanol solutions

et al. 2012

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This work concerns the investigation of stability constants of silver(I) ions with the tetrapyrrolidinyl-PNP-lariat ether L1 in acetonitrile solution and tetramorpholinyl-PNP-lariat ether L2 in acetonitrile and methanol solutions. The new tetramorpholinyl-PNP-lariat ether L2 was synthesized on the basis of the procedure described in a previous publication. Stability constants of complexes with silver ions were determined using a simple potentiometric titration. Furthermore, NMR spectra were obtained to investigate how the complexation of silver(I) ions by the investigated macrocyclic ligand occurs. Spectrometric data analyses and potentiometric measurements indicate that complexation of Ag + involves participation of the endocyclic nitrogen atom of the cyclophosphazene ring and polyether oxygen donors. As regards L1 the stability of the obtained complex is influenced by pyrrolidinyl groups. On the other hand, L2 includes the morpholinyl subunits attached to the exocyclic P atom, having in their structure the oxygen atom, which pulls out the electrons of the cyclophosphazene ring and thereby destabilizes the formation of a coordination system.

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“…THF is also probably solvating the sodium ion more strongly than the lithium ion and this too would enhance the reactivity of its alkoxide ion. Conductometric studies on the titration of alkali metal acetates with perchloric acid in acetic acid [37] and complexation studies of both the alkali metal ions with phosphazene lariat ethers by Bartsch et al [38] indicate that ion-pairing will be stronger for lithium than for sodium alkoxides. The counter-n of the alkoxide is likely to be freer in the sodium reagent, making it more reactive than the lithium analogue, and hence proportionally more ansa derivative is obtained with the sodium alkoxide.…”

Section: (V) Explanation Of the Difference In Formation Of Spiro Ansmentioning

confidence: 99%

Competitive formation of spiro and ansa derivatives in the reactions of tetrafluorobutane-1,4-diol with hexachlorocyclotriphosphazene: A comparison with butane-1,4-diol

et al. 2006

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Beşli, Serap; Coles, Simon J.; Davies, David B.; Eaton, Robert J.; Kılıç, Adem; Shaw, Robert A. (2006) Competitive formation of spiro and ansa derivatives in the reactions of tetrafluorobutane-1,4-diol with hexachlorocyclotriphosphazene: a comparison with butane-1,4-diol. Polyhedron 25 (4): [963][964][965][966][967][968][969][970][971][972][973][974] This is an author-produced version of a paper published in Polyhedron . This version has been peer-reviewed, but does not include the final publisher proof corrections, published layout, or pagination. All articles available through Birkbeck ePrints are protected by intellectual property law, including copyright law. Any use made of the contents should comply with the relevant law. AbstractReaction of hexachlorocyclotriphosphazene, N 3 P 3 Cl 6 (1), in two stoichiometries (1:1.2 and 1:3)with the sodium derivative of the fluorinated diol, 2,2,3,3-tetrafluorobutane-1,4-diol, (2), in THF solution at room temperature afforded six products, whose structures have been characterized by X-ray crystallography and 1 H, 19 F and 31 P NMR spectroscopy: the mono-spiro compound, N 3 P 3 Cl 4 (OCH 2 CF 2 CF 2 CH 2 O), (3), its ansa isomer, (4), a di-spiro derivative N 3 P 3 Cl 2 (OCH 2 CF 2 CF 2 CH 2 O) 2 , (5), its spiro-ansa (6) and non-gem cis bis-ansa (7) isomers and a tri-spiro compound N 3 P 3 (OCH 2 CF 2 CF 2 CH 2 O) 3 , (8). The tri-spiro derivative (8) was also formed in the reaction of the ansa compound (4) with diol (2) in a 1:3 ratio in THF at room temperature.The reactions of (1) with step-wise additions of (2) were also investigated at low temperature (-78 0 C) to give the same range of products as at room temperature. The results of all reactions are compared with previous work on the reactions of (1) with butane-1,4-diol/pyridine mixtures and with the reaction of hexafluorocyclotriphosphazene, N 3 P 3 F 6 (9), with the silyl derivative of the diol (2), (Me 3 SiOCH 2 CF 2 ) 2 , in a 1:0.4 mole ratio in the same solvent, THF.3

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Cited by 20 publications

References 27 publications

Doubly-bridged PNP-lariat ethers and their complexes with silver(i) ions in methanol solution

Doubly-bridged PNP-lariat ethers and their complexes with silver(i) ions in methanol solution

Complexes of silver(i) ions with tetrapyrrolidinyl- and tetramorpholinyl-PNP-lariat ethers in acetonitrile and methanol solutions

Competitive formation of spiro and ansa derivatives in the reactions of tetrafluorobutane-1,4-diol with hexachlorocyclotriphosphazene: A comparison with butane-1,4-diol

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