A Macrobicyclic Thiophosphonamide Polyether Ligand

Oostenryck, Luc Van; Tinant, Bernard; Declercq, Jean‐Paul; Dutasta, Jean‐Pierre

doi:10.1107/s0108270194003914

Cited by 3 publications

(3 citation statements)

References 6 publications

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“…In the course of our investigations to produce macrocyclic phosphorus ligands, we have been particularly interested by the cyclic derivatives obtained from the reaction of diamines with a diaminophosphine that can lead to macrocyclic phosphoramides [2][3][4][5][6]. From such compounds, nucleophilic attack at phosphorus could lead to new interesting structures.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of ethyl-{3-thioxo-2-(3-thioxo-11,14, 17,20-tetraoxa-2,4-diaza-3λ5-phospha-tricyclo[19.4.0.05,10]- pentacosa-l(25),5(10),6,8,21,23-hexaene-3-yl)-11,14,17,20-tetraoxa-2,4-diaza-3λ5-phospha-tricyclo-[19.4.0.05,10]- pentacosa-1(25),5(10),6,8,21,23-hexaene-3-yl}-amine monohydrate, (C38H49N5O8P2S2) · H2O

Tinant¹,

Declercq²,

Mulatier³

et al. 2002

Zeitschrift Für Kristallographie - New Crystal Structures

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C38H51N5O9P2S2, triclinic, PI (No. 2), a = 9.444(2) Â, b = 11.017(3) Â, c = 21.138(5) Â, α = 79.23(2)°, β = 84.09(2)°, γ = 71.35(3)°, V= 2044.9 Â*. Z= 2, R&(F) = 0.072, wÄreffF 2 ; = 0.214, 7·= 293 Κ. Source of materialThe synthesis of the title compound was carried out by heating the diazadiphosphetidine precursor [ 1 ], with an excess of ethylamine in toluene. Under these conditions, we isolated a solid compound, which gave suitable crystals for X-ray diffraction analysis.

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Section: Discussionmentioning

confidence: 99%

Crystal structure of ethyl-{3-thioxo-2-(3-thioxo-11,14, 17,20-tetraoxa-2,4-diaza-3λ5-phospha-tricyclo[19.4.0.05,10]- pentacosa-l(25),5(10),6,8,21,23-hexaene-3-yl)-11,14,17,20-tetraoxa-2,4-diaza-3λ5-phospha-tricyclo-[19.4.0.05,10]- pentacosa-1(25),5(10),6,8,21,23-hexaene-3-yl}-amine monohydrate, (C38H49N5O8P2S2) · H2O

Tinant¹,

Declercq²,

Mulatier³

et al. 2002

Zeitschrift Für Kristallographie - New Crystal Structures

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“…This article describes a new family of phosphorus ligands in which a phosphorylated binding site is introduced into a semirigid macrocyclic structure. We have recently shown that the synthesis of macrocyclic phosphonamides and the formation of metal ion complexes is possible through the combination of a crown ether unit and a phosphonamide-containing building block. − …”

Section: Introductionmentioning

confidence: 99%

“…The standard strategy for the synthesis of macrocyclic phosphonamides is the preparation of an intermediate diamine followed by the cyclization of this diamine with a diaminophosphane, and finally oxidation of the parent phosphorus(III) macrocycle. , This general approach can be applied to a variety of diamines and diaminophosphanes, and syntheses of 17−27-membered-ring phosphorus crown compounds have been developed …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Conformational Studies, X-ray Structures, and Complexation Properties of Semirigid Macrocyclic Phosphonamides

Delangle¹,

Dutasta²,

Oostenryck³

et al. 1996

J. Org. Chem.

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The semirigid phosphonamide ligands 1-5 have been synthesized from the macrocyclic precursors 6-9 by reaction with 1,3-propanediol ditosylate or 1,2-dichloroethane. For the thiophosphoryl compounds 1 and 2, and the phosphoryl derivative 5, the reactions were carried out in biphasic aqueous NaOH solutions. The phosphoryl derivatives 3 and 4 were better obtained from NaH in anhydrous tetrahydrofuran. The conformations of the hosts in solution were deduced from low-temperature NMR and NOE difference experiments. Conformational equilibria between exo and endo forms are observed for the 18-membered macrocycles 1 and 3. The exo conformer predominates in solution for the 21-membered macrocycle 2, whereas 4 exists as rapidly exchanging conformers. The X-ray crystal structures of macrocycles 1, 2, and 5 have been determined as well as the complexes 1.Hg(SCN)(2) and 5.LiNO(3). In the Hg(2+) complex the metal ion is located out of the macrocyclic cavity and is coordinated to the thiophosphoryl unit. In 5.LiNO(3)()()the Li(+) cation is located inside the macrocyclic cavity and is coordinated to a tetrahedral array of oxygen donors. Free energies of complexation (DeltaG degrees ) of the phosphorylated ligands 3-5 with alkali metal and ammonium cations were determined in CHCl(3) saturated with H(2)O by picrate extraction experiments. The -DeltaG degrees values are greatest for 4 complexing K(+) and NH(4)(+) (7.3 and 8.0 kcal/mol, respectively). The relationships between structure and binding are discussed.

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Formation and X-Ray Structural Characterization of the Chiral

Declercq¹,

Tinant²,

Dutasta³

et al. 1999

Phosphorus, Sulfur, and Silicon and the Related Elements

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A Macrobicyclic Thiophosphonamide Polyether Ligand

Abstract: Two crystal structures of a macrobicyclic oligoether compound, 31 -phenyl-8,11,14,17,20-pentoxa-1,27-diaza-31-phosphatetracyclo[25.3

Cited by 3 publications

References 6 publications

Synthesis, Conformational Studies, X-ray Structures, and Complexation Properties of Semirigid Macrocyclic Phosphonamides

Formation and X-Ray Structural Characterization of the Chiral

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