Two polymorphs of (2-carboxyethyl)(phenyl)phosphinic acid

Hu, Qiao Sheng; Zhang, Xiu Zhi; Luo, Shu Fen; Sun, Yu; Du, Zi‐Yi

doi:10.1107/s0108270111013163

Cited by 8 publications

(5 citation statements)

References 6 publications

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“…There are phosphinic acids that aggregate in cyclic dimers due to steric reasons. The O···O distances in these dimers are about 2.50 Å or shorter as well. − ,, Some ideas can be extracted from the XRD structure of 3-(hydroxy(phenyl)phosphoryl)propanoic acid . In Figure is shown a scheme of the H-bond network in this structure.…”

Section: Discussionmentioning

confidence: 98%

“…Structure of a polymorph of 3-(hydroxy(phenyl)phosphoryl)propanoic acid . The numerical data stand for the O···O distances of COH···OP and POH···OP H-bonds.…”

Section: Discussionmentioning

confidence: 99%

“…[53][54][55]43,44 Some ideas can be extracted from the XRD structure of 3-(hydroxy(phenyl)phosphoryl)propanoic acid. 56 In Figure 10 is shown a scheme of the H-bond network in this structure. The POH and PO moieties of neighboring molecules form an H-bond chain.…”

Section: ■ Discussionmentioning

confidence: 99%

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P═O Moiety as an Ambidextrous Hydrogen Bond Acceptor

et al. 2018

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Hydrogen bond patterns of crystals of phosphinic, phosphonic, and phosphoric acids and their cocrystals with phosphine oxides were studied using 31 P NMR and single-crystal X-ray diffraction. Two main factors govern these patterns and favor or prevent the formation of cocrystals. The first one is a high proton-accepting ability of the PO moiety in these acids. As a result, this moiety effectively competes with other proton acceptors for hydrogen bonding. For example, this moiety is a stronger proton acceptor than the CO moiety of carboxylic acids. The second factor is the inclination of the PO moiety of both the acids and the oxides to form two hydrogen bonds at once. The peculiarity of these bonds is that they weaken each other to a little degree only. In order to highlight this point, we are using the term "ambidextrous". These two features should govern the interactions of PO moiety with water and other proton donors and acceptors in molecular clusters, the active sites of enzymes, soft matter, and at surfaces.

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Section: Discussionmentioning

confidence: 98%

“…Structure of a polymorph of 3-(hydroxy(phenyl)phosphoryl)propanoic acid . The numerical data stand for the O···O distances of COH···OP and POH···OP H-bonds.…”

Section: Discussionmentioning

confidence: 99%

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P═O Moiety as an Ambidextrous Hydrogen Bond Acceptor

et al. 2018

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“…(2-Carboxyethyl)(phenyl)phosphinic acid represents another type of ligand used for obtaining metal–organic frameworks because it features polar phosphinic acid and carboxy moieties at the ends of a flexible –(CH 2 )n– spacer (n = 2), which is an efficient asymmetric ligand for inducing the formation of noncentrosymmetric structures for metal complexes [ 40 , 41 ]. 2-Carboxyethyl (phenyl)phosphinic acid has also been used as a flame retardant prepared via the reaction with melamine [ 42 ] or with dimethyl terephthalate and ethylene glycol [ 43 ] or with 2,5-furandicarboxylic acid and 1,6-hexanediol [ 44 ].…”

Section: Introductionmentioning

confidence: 99%

Hybrid Coordination Networks for Removal of Pollutants from Wastewater

Marganovici

Maranescu²,

Visa³

et al. 2022

IJMS

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The adsorption properties of two coordination polymers, resulting from the reaction of divalent metal (Ca2+ or Co2+) salts with (2-carboxyethyl)(phenyl)phosphinic acid, are presented in this paper. The structural and textural characterization before and after adsorption experiments is presented. The adsorbent materials were prepared using the hydrothermal procedure. The compound Ca[O2P(CH2CH2COOH)(C6H5)]2 (CaCEPPA) has a layered topology, with the phenyl groups oriented into the interlayer space and crystallizes in the monoclinic system. Compound Co2[(O2P(CH2CH2COO)(C6H5)(H2O)]2·2H2O (CoCEPPA) has a 1D structure composed of zig-zag chains. The adsorption performances of CaCEPPA and CoCEPPA materials were tested in the removal of cadmium and lead from aqueous solutions. The optimum pH of ions adsorption was found to be five for both adsorbent materials. Pseudo-first and second-order kinetic models were used for fitting kinetic experimental data, and Langmuir and Freundlich isotherms were used for modeling the equilibrium experimental data. The pseudo-second-order kinetic model and Langmuir isotherm best described the adsorption of Cd and Pb ions onto the studied materials, judging from the results of the error function (correlation coefficient, sum of square error, chi-square test, and average relative error) analysis. The studied materials present a higher affinity for Cd ions compared with the adsorption capacity developed for the removal of Pb ions from aqueous solutions. CoCEPPA showed the highest adsorption performance in the removal process of metal ions from aqueous solutions compared with CaCEPPA (qm = 54.9 mg Cd2+/g of CoCEPPA, qm = 36.5 mg Cd2+/g of CaCEPPA).

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“…Recently, we have undertaken research work on the coordination and supramolecular chemistry of an asymmetric bifunctional ligand, (2-carboxyethyl)(phenyl)phosphinic acid (H 2 L) . Such a ligand features two formally analogous carboxylate and phosphinate moieties (i.e., both feature two potentinal O donors) separated by a flexible −CH 2 CH 2 – spacer, with the latter being further bonded to a phenyl group.…”

Section: Introductionmentioning

confidence: 99%

Temperature-Dependent Crystal Self-Assembly, Disassembly, and Reassembly Among Three Cadmium(II) Carboxylate-Phosphinates

Dong

Zhao

et al. 2012

Crystal Growth & Design

Self Cite

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A metastable three-dimensional cadmium(II) coordination polymer with (2-carboxyethyl)(phenyl)phosphinate (L 2− ) and 4,4′-bipyridine (bipy) as ligands, namely, [Cd(L)-(bipy)(H 2 O) 2 ] (1), can be converted to two new two-dimensional/ three-dimensional varieties under hydrothermal treatments at different temperatures, that is, [Cd(L)(bipy)] (2) and [Cd(L)-(bipy) 0.5 ]•0.5H 2 O ( 3). Their syntheses, crystal structures, structural transformations, and luminescent properties are presented. In addition, 1 shows a second harmonic generation response that is ∼0.3 times that of KDP (KH 2 PO 4 ).

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Two polymorphs of (2-carboxyethyl)(phenyl)phosphinic acid

Cited by 8 publications

References 6 publications

P═O Moiety as an Ambidextrous Hydrogen Bond Acceptor

P═O Moiety as an Ambidextrous Hydrogen Bond Acceptor

Hybrid Coordination Networks for Removal of Pollutants from Wastewater

Temperature-Dependent Crystal Self-Assembly, Disassembly, and Reassembly Among Three Cadmium(II) Carboxylate-Phosphinates

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