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Journal articles on the topic 'Phosphonic acid'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 March 2023

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1

Weinberger, Christian, Tatjana Heckel, Patrick Schnippering, Markus Schmitz, Anpeng Guo, Waldemar Keil, Heinrich C. Marsmann, Claudia Schmidt, Michael Tiemann, and René Wilhelm. "Straightforward Immobilization of Phosphonic Acids and Phosphoric Acid Esters on Mesoporous Silica and Their Application in an Asymmetric Aldol Reaction." Nanomaterials 9, no. 2 (February 12, 2019): 249. http://dx.doi.org/10.3390/nano9020249.

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The combined benefits of moisture-stable phosphonic acids and mesoporous silica materials (SBA-15 and MCM-41) as large-surface-area solid supports offer new opportunities for several applications, such as catalysis or drug delivery. We present a comprehensive study of a straightforward synthesis method via direct immobilization of several phosphonic acids and phosphoric acid esters on various mesoporous silicas in a Dean–Stark apparatus with toluene as the solvent. Due to the utilization of azeotropic distillation, there was no need to dry phosphonic acids, phosphoric acid esters, solvents, or silicas prior to synthesis. In addition to modeling phosphonic acids, immobilization of the important biomolecule adenosine monophosphate (AMP) on the porous supports was also investigated. Due to the high surface area of the mesoporous silicas, a possible catalytic application based on immobilization of an organocatalyst for an asymmetric aldol reaction is discussed.

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2

Maurya, Sandip, Katie Lim, Zhendong Hu, Hongfei Jia, Jeffrey Michael Klein, and Yu Seung Kim. "Alkyl Phosphonic Acids: An Alternative to Phosphoric Acid in HT-Pemfcs." ECS Meeting Abstracts MA2022-02, no. 41 (October 9, 2022): 1510. http://dx.doi.org/10.1149/ma2022-02411510mtgabs.

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Phosphoric acid has received the most attention as a choice of electrolyte for a high-temperature proton exchange membrane fuel cell (HT-PEMFC). Phosphoric acid has many attractive properties such as high anhydrous conductivity, good compatibility with hydrocarbon membranes, and thermal stability [1], which enables high fuel cell performance under anhydrous and elevated operating temperatures (140-180 oC) [2-3]. However, phosphoric acid has undesirable properties such as high catalyst poisoning, high evaporation rate at > 200 oC, and low acid retention from the doped membrane. Alkyl phosphonic acid may correct some of the drawbacks of phosphoric acid, improving fuel cell performance and durability. In this presentation, we report the technical challenges and possible resolutions for HT-PEMFCs using alkyl phosphonic acid doped membranes. We focus on the effects of alkyl phosphonic acid on hydrogen oxidation and oxygen reduction reactions of Pt-based catalysts. In addition, we discuss the membrane selection of robust operation of alkyl phosphonic acid-based HT-PEMFC. References: [1] A.S. Lee, Y.-K. Choe, I. Matanovic, Y.S. Kim, Journal of Materials Chemistry A, 7 (2019) 9867-9876. [2] K.H. Lim, A.S. Lee, V. Atanasov, J. Kerres, E.J. Park, S. Adhikari, S. Maurya, L.D. Manriquez, J. Jung, C. Fujimoto, I. Matanovic, J. Jankovic, Z. Hu, H. Jia, Y.S. Kim, Nature Energy, 7 (2022) 248-259. [3] V. Atanasov, A.S. Lee, E.J. Park, S. Maurya, E.D. Baca, C. Fujimoto, M. Hibbs, I. Matanovic, J. Kerres, Y.S. Kim, Nature Materials, 20 (2021) 370-377.

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3

Sevrain, Charlotte M., Mathieu Berchel, Hélène Couthon, and Paul-Alain Jaffrès. "Phosphonic acid: preparation and applications." Beilstein Journal of Organic Chemistry 13 (October 20, 2017): 2186–213. http://dx.doi.org/10.3762/bjoc.13.219.

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The phosphonic acid functional group, which is characterized by a phosphorus atom bonded to three oxygen atoms (two hydroxy groups and one P=O double bond) and one carbon atom, is employed for many applications due to its structural analogy with the phosphate moiety or to its coordination or supramolecular properties. Phosphonic acids were used for their bioactive properties (drug, pro-drug), for bone targeting, for the design of supramolecular or hybrid materials, for the functionalization of surfaces, for analytical purposes, for medical imaging or as phosphoantigen. These applications are covering a large panel of research fields including chemistry, biology and physics thus making the synthesis of phosphonic acids a determinant question for numerous research projects. This review gives, first, an overview of the different fields of application of phosphonic acids that are illustrated with studies mainly selected over the last 20 years. Further, this review reports the different methods that can be used for the synthesis of phosphonic acids from dialkyl or diaryl phosphonate, from dichlorophosphine or dichlorophosphine oxide, from phosphonodiamide, or by oxidation of phosphinic acid. Direct methods that make use of phosphorous acid (H3PO3) and that produce a phosphonic acid functional group simultaneously to the formation of the P–C bond, are also surveyed. Among all these methods, the dealkylation of dialkyl phosphonates under either acidic conditions (HCl) or using the McKenna procedure (a two-step reaction that makes use of bromotrimethylsilane followed by methanolysis) constitute the best methods to prepare phosphonic acids.

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4

Turgis, Raphaël, Antoine Leydier, Guilhem Arrachart, Fabien Burdet, Sandrine Dourdain, Gilles Bernier, Manuel Miguirditchian, and Stéphane Pellet-Rostaing. "Uranium Extraction from Phosphoric Acid Using Bifunctional Amido-Phosphonic Acid Ligands." Solvent Extraction and Ion Exchange 32, no. 5 (June 6, 2014): 478–91. http://dx.doi.org/10.1080/07366299.2014.898435.

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5

Bruckmann, J., C. Krüger, C. W. Lehmann, W. Leitner, J. Rust, and C. Six. "Ethylenebis(phosphonic acid)." Acta Crystallographica Section C Crystal Structure Communications 55, no. 4 (April 15, 1999): 695–96. http://dx.doi.org/10.1107/s0108270198016448.

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6

YURT, AYSEL, and ESRA SOLMAZ. "PHOSPHONIC ACID MONOLAYERS FOR CORROSION PROTECTION OF COPPER: EQCM AND EIS INVESTIGATIONS." Surface Review and Letters 27, no. 06 (November 1, 2019): 1950166. http://dx.doi.org/10.1142/s0218625x1950166x.

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Preparation, characterization and application of protective phosphonic acid monolayers formed by 1-Aminohexyl phosphonic acid (AHP), 1,4-butanediphosphonic acid (BDPA), 1-amino-1,3-dimethylbutyl phosphonic acid (ADBP) on copper surface as anticorrosive self-assembled molecular monolayers (SAMs) have been investigated by atomic force microscopy (AFM) analysis, electrochemical impedance spectroscopy (EIS) and in situ electrochemical quartz crystal microbalance (EQCM) techniques. Film formation and growth were monitored by EQCM and the step-by-step construction of monolayer was investigated through measurement of the frequency change, which corresponds to mass change due to the adsorption of molecules. Observed increase in electrode mass suggests that SAMs formed on copper surface by the adsorption of phosphonic acids. Results clearly demonstrate that adsorbed amounts of phosphonic acids were strongly influenced by immersion time and molecular structure. Quantum chemical calculations were performed by semi-empirical PM6 method, in order to explain the relationship between molecular structure and adsorption mechanism. Quantum chemical parameters of phosphonic acids propound that adsorption of molecules on copper surface has a chemical mechanism. Corrosion protection ability of SAMs against the acidic corrosion of copper has been evaluated in 0.1[Formula: see text]M H2SO4 solution. It was found that phosphonic acid SAMs act as protective barrier and the protection efficiencies increased in the following order: [Formula: see text].

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7

Khanvilkar, Aditya N., and Ashutosh V. Bedekar. "Synthesis and characterization of chiral aza-macrocycles and study of their enantiomer recognition ability for organo-phosphoric acid and phosphonic acid derivatives by 31P NMR and fluorescence spectroscopy." Organic & Biomolecular Chemistry 14, no. 9 (2016): 2742–48. http://dx.doi.org/10.1039/c5ob02616d.

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Two diastereomers of optically active N,O-containing new macrocycles with dual chirality were synthesized and evaluated for chiral discrimination of organo phosphoric and phosphonic acids by ³¹P NMR and fluorescence spectroscopy.

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8

Paladini, A., C. Calcagni, T. Di Palma, M. Satta, M. Speranza, D. Scuderi, A. Laganà, G. Fago, and A. Giardini Guidoni. "Laser production of gas phase complexes of metalα-aminophosphonic acid mixtures and their role in chiral recognition." International Journal of Photoenergy 3, no. 4 (2001): 217–21. http://dx.doi.org/10.1155/s1110662x01000290.

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Clusters between first-group metal ions and chiralα-aminophosphonic acids have been readily generated by Pulsed Laser Ablation (PLA) and by Electrospray Ionization (ESI) and their fragmentation investigated by mass spectrometry. The complexes studied have the general formula[Me(I)Cl2]+, where Me(I) is H, Li, Na, or K, C is (R)-(—)-(1-aminoethyl) phosphonic acid(ER)and (S)-(+)-(1-aminoethyl) phosphonic acid(ES),(1R)-(+)-(1-amino-2-methylpropyl) phosphonic acid(PR)and (1S)-(—)-(1-amino-2-methylpropyl) phosphonic acid(PS),(1R)-(-)-(1-amino-hexyl) phosphonic acid (HR) and (1S)-(+)-(1-amino-hexyl) phosphonic acid (HS), o-phospho-L-serine (SS)ando-phospho-D-serine(SR), and L is a referenceα-aminophosphonic acid (E, P, H or S) of defined configuration. Collision induced dissociation (CID) of diastereomeric[Me(I)Cl2]+complexes leads to fragmentation patterns characterized by[Me(I)Cl]+/[Me(I)L2]+abundance ratios which depend upon the configuration of solute C. These different spectral features were correlated to the different stability of the diastereomeric[Me(I)CRL]+and[Me(I)CSL]+complexes in the gas phase.

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9

Kamber, Matthias, and George Just. "γ-Phosphono-γ-lactones. The use of allyl esters as easily removable phosphonate protecting groups." Canadian Journal of Chemistry 63, no. 4 (April 1, 1985): 823–27. http://dx.doi.org/10.1139/v85-136.

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During the synthesis of γ-lactones bearing a phosphonic acid group at the γ-position, difficulties were encountered generating the free phosphonic acids from corresponding esters. A protecting group used for carboxylic acids was adapted to phosphonic acids, making this transformation easy.

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10

Abbenante, Giovanni, Robert Hughes, and Rolf H. Prager. "Potential GABA B Receptor Antagonists. IX The Synthesis of 3-Amino-3-(4-chlorophenyl)propanoic Acid, 2-Amino-2-(4-chlorophenyl)ethylphosphonic Acid and 2-Amino-2-(4-chlorophenyl)ethanesulfonic Acid." Australian Journal of Chemistry 50, no. 6 (1997): 523. http://dx.doi.org/10.1071/c96216.

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This paper describes the synthesis of 3-amino-3-(4-chlorophenyl)propanoic acid and the corresponding phosphonic and sulfonic acids, lower homologues of baclofen, phaclofen and saclofen respectively. The chlorinated acids were all weak specific antagonists of GABA at the GABAB receptor, with the sulfonic acid (pA2 4·0) being stronger than the phosphonic acid (pA2 3·8) and carboxylic acid (pA2 3·5).

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11

Su, Debao, Cai Yun Guo, Roger D. Willett, Brian Scott, Robert L. Kirchmeier, and Jean'ne M. Shreeve. "Synthesis of trans-1,2-difluoroethenediylbis(phosphonic acid) and other unsaturated phosphonic acids." Journal of the American Chemical Society 112, no. 8 (April 1990): 3152–55. http://dx.doi.org/10.1021/ja00164a042.

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12

McNichols, Brett W., Joshua T. Koubek, and Alan Sellinger. "Single-step synthesis of styryl phosphonic acids via palladium-catalyzed Heck coupling of vinyl phosphonic acid with aryl halides." Chemical Communications 53, no. 92 (2017): 12454–56. http://dx.doi.org/10.1039/c7cc05909d.

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13

Coletti-Previero, M.-A., M. Pugnière, H. Mattras, J. C. Nicolas, and A. Previero. "Selective retention of organic phosphate esters and phosphonates on aluminium oxide." Bioscience Reports 6, no. 5 (May 1, 1986): 477–83. http://dx.doi.org/10.1007/bf01116139.

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Compounds containing the −PO3H2 function, such as monoesters of phosphoric acid and phosphonic acids, specifically bind to aluminium oxide in aqueous solution under experimental conditions where non-phosphorylated compounds are completely desorbed. The bound organic phosphate can be specifically displaced by aqueous solution of inorganic phosphates thus allowing their separation or detection by a technique similar to that of affinity chromatography. The consequences of this finding for phosphate compound biochemistry are discussed.

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14

Köken, Nesrin. "Polymers containing amino bis(methylene phosphonic acid) groups for scale inhibition." Pigment & Resin Technology 48, no. 1 (January 7, 2019): 73–83. http://dx.doi.org/10.1108/prt-01-2017-0007.

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Purpose The purpose of this paper is to prepare poly[allyl amino bis(methylene phosphonic acid)-ran-acrylic acid]s by two different routes. In the first route, poly(allyl amine-ran-acrylic acid)s were produced by radical copolymerization of a mixture of ally amine and acrylic acid, then converted into poly[allyl amino bis(methylene phosphonic acid)-ran-acrylic acid]s by the Mannich reaction with a mixture of formaldehyde and phosphonic acid. In the second route, allyl amino bis(methylene phosphonic acid) monomer was synthesized and copolymerised with acrylic acid. The aim of this work is to produce low-molecular-weight copolymer with the low amount of nitrogen and phosphorous having better scale inhibiting performance than commercial low-molecular-weight poly(acrylic acid)s. Design/methodology/approach Poly(allyl amine-ran-acrylic acid)s were prepared by radical copolymerisation of a mixture of ally amine and acrylic acid, and the molecular weight of copolymers was regulated by using an effective chain transfer compound and the formed copolymer was reacted with a mixture of formaldehyde and phosphorous acid. Allyl amino bis(methylene phosphonic acid) monomer was prepared and then copolymerised with acrylic acid using radical initiators. Findings Poly[allyl amino bis(methylene phosphonic acid)-ran-acrylic acid] produced with both routes, especially low-molecular weight ones have better anti-scaling performance than low-molecular-weight commercial poly(acrylic acid). Research limitations/implications By using an excess of formaldehyde and phosphonic acid, a limited increase in the conversion of amine groups of poly(allyl amine-ran-acrylic acid) to amino methylene phosphonic acid groups was achieved, so unreacted amine groups were always present in the structure of the final copolymers. Practical implications The low-molecular-weight poly[allyl amino bis(methylene phosphonic acid)-ran-acrylic acid] may be used as a better anti-scaling polymer in industry. Social implications The low-molecular-weight poly[allyl amino bis(methylene phosphonic acid)-ran-acrylic acid] is an alternative polymer for scale inhibition in the water boilers. Originality/value The low-molecular-weight poly[allyl amino bis(methylene phosphonic acid)-ran-acrylic acid] copolymers containing both carboxylic acid and amino bis(methylene phosphonic acid) are more effective anti-scaling additives than poly(acrylic acid)s in water boilers.

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15

Su, Debao, Wenbiao Cen, Robert L. Kirchmeier, and Jean'ne M. Shreeve. "Synthesis of fluorinated phosphonic, sulfonic, and mixed phosphonic/sulfonic acids." Canadian Journal of Chemistry 67, no. 11 (November 1, 1989): 1795–99. http://dx.doi.org/10.1139/v89-278.

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The acids (HO)2P(O)CFHSO3H, (HO)2P(O)(CF2)4O(CF2)2SO3H, H(CF2)2O(CF2)2P(O)(OH)2, H(CF2)2O(CF2)4P(O)(OH)2, (HO)2P(O)(CF2)2O(CF2)4H, and the acid precursor (C2H5O)2P(O)CF(SO3Na)2 have been synthesized. Elemental analysis, 19F, 1H, and 31P NMR, and mass spectroscopy were used for characterization of these materials. They are very strong acids, and exhibit a high degree of stability in aqueous solution at elevated temperature, which makes them attractive candidates for use as electrolytes in fuel cells. Keywords: fluorinated phosphonic acids; fluorinated sulfonic acids; 1H, 19F, 31P NMR.

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16

Gheonea, Ramona, Carmen Mak, Eleonora Cornelia Crasmareanu, Vasile Simulescu, Nicoleta Plesu, and Gheorghe Ilia. "Surface Modification of SnO2with Phosphonic Acids." Journal of Chemistry 2017 (2017): 1–7. http://dx.doi.org/10.1155/2017/2105938.

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The aim of the present work was the study of phosphonic acids grafting on the surface of SnO2at different molar ratios. In this paper we describe the functionalization of SnO2surfaces with phosphonic acids RPO(OH)2. The surface modification process was achieved by using phenyl-phosphonic acid (PPA) and vinyl-phosphonic acid (VPA). The synthesized materials were investigated by using FT-IR, TGA (in air and in nitrogen), EDX, ESEM, and TEM methods. This synthetic approach has many advantages: films with optical quality and controlled thickness can be obtained using low temperatures and cheap raw materials, by using “green chemistry” synthetic routes. The hybrid materials have structures diversity and fascinating applications, attracting attention for a long time, due to their potential.

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17

Abe, Yasushi, Toru Amaya, Yuhi Inada, and Toshikazu Hirao. "Characterization of self-doped conducting polyanilines bearing phosphonic acid and phosphonic acid monoester." Synthetic Metals 197 (November 2014): 240–45. http://dx.doi.org/10.1016/j.synthmet.2014.09.020.

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18

Kozyra, Kinga, Magdalena Klimek-Ochab, Małgorzata Brzezińska-Rodak, and Ewa Żymańczyk-Duda. "Direct determination of enantiomeric enrichment of chiral, underivatized aminophosphonic acids — useful for enantioselective bioconversion results evaluation." Open Chemistry 11, no. 9 (September 1, 2013): 1542–47. http://dx.doi.org/10.2478/s11532-013-0277-5.

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AbstractAbstract The possibility of applying 31P NMR spectroscopy for the determination of the enantiomeric excess of the racemic mixture of non-derivatized aminophosphonic acids with small side chains has been investigated. It is proven, that the effectiveness of the application of a chiral solvating agent strongly depends on the concentration of applied shift reagent and on the pH of the particular experiment. Effectual resolution protocols are elaborated for following phosphonic acids: 1-aminoethanephosphonic acid, 1-amino-2-methylpropanephosphonic acid, 1-aminophenylmethanephosphonic acid, 1-aminophenylmethane-phosphonic acid and 1-amino-2-phenylethanephosphonic acid. Graphical abstract

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19

Erbacher, Martin, and Franz-Peter Montforts. "Synthesis of novel porphyrin and chlorin phosphonic acids and their immobilization on metal oxides." Journal of Porphyrins and Phthalocyanines 15, no. 09n10 (September 2011): 1070–77. http://dx.doi.org/10.1142/s108842461100404x.

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In this study an easy and flexible access to porphyrin and chlorin phosphonic acids is presented. Novel types of phosphonic acid terminated porphyrins and chlorins were synthesized starting from commercially available red blood pigment hemin chloride. Phosphonic acid groups were linked to the porphyrinoids by amide coupling via appropriate spacer moieties. Self-assembled monolayers of the synthesized phosphonates on mesoporous TiO2 electrodes of approximately 3 μm thickness were formed. Surface concentrations in a range of 1 to 4 × 10-8 mol.cm-2 could be determined by UV-vis spectroscopy.

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20

Burton, Donald J., Anil S. Modak, Ranil Guneratne, Debao Su, Wenbiao Cen, Robert L. Kirchmeier, and Jean'ne M. Shreeve. "Synthesis of (sulfodifluoromethyl)phosphonic acid." Journal of the American Chemical Society 111, no. 5 (March 1989): 1773–76. http://dx.doi.org/10.1021/ja00187a033.

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21

Schulz, P. C., B. S. Fern�ndez-Band, B. Vuano, M. Palomeque, and A. L. Allan. "Studies on styrene phosphonic acid." Colloid & Polymer Science 274, no. 8 (August 1996): 741–46. http://dx.doi.org/10.1007/bf00654669.

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22

A.Nithya, A. Nithya, and S. Rajendran S.Rajendran. "Corrosion Inhibition of Aluminium by Diethylene Triamine Pentamethylene Phosphonic Acid." Indian Journal of Applied Research 3, no. 10 (October 1, 2011): 1–3. http://dx.doi.org/10.15373/2249555x/oct2013/18.

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23

Zhang, Rui, Yundi Zhang, Chunhua Ge, Jinpeng Miao, and Xiangdong Zhang. "Two closely related {4-[(N-substituted amino)(diethoxyphosphoryl)methyl]phenyl}boronic acids." Acta Crystallographica Section C Structural Chemistry 73, no. 1 (January 1, 2017): 57–60. http://dx.doi.org/10.1107/s2053229616019707.

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Organic phosphonic acids and organic phosphonic acid esters have been of much interest due to their applications in the fields of medicine, agriculture and industrial chemistry. Boronic acids can act as synthetic intermediates and building blocks and are used in sensing, protein manipulation, therapeutics, biological labelling and separation. The additional introduction of an aminophosphonic acid group into a boronic acid may give new opportunities for application. To study the structure of such multifunctional compounds, we prepared two new derivatives which can be easily converted to the corresponding phosphonic acids. In the title compounds, {4-[(butylamino)(diethoxyphosphoryl)methyl]phenyl}boronic acid monohydrate, C15H27BNO5P·H2O, (I), and {4-[(diethoxyphosphoryl)(4-nitroanilino)methyl]phenyl}boronic acid, C17H22BN2O7P, (II), three different substituents are attached to a central C—H group, namely 4-boronophenyl, diethoxyphosphoryl and amine. Compound (I) crystallizes as a monohydrate and OB—H...N hydrogen bonds link neighbouring molecules into chains along the [001] direction. The solvent water molecule connects two such chains running in opposite directions. Compound (II) crystallizes as an ansolvate and classical hydrogen bonds result in a layer structure in the (001) plane.

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24

Zhou, L., and H. A. Nasr-El-Din. "Phosphonic-Based Hydrofluoric Acid: Interactions With Clay Minerals and Flow in Sandstone Cores." SPE Journal 21, no. 01 (February 18, 2016): 264–79. http://dx.doi.org/10.2118/164472-pa.

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Summary Regular mud acid, which is composed of hydrochloric acid (HCl) and hydrofluoric (HF) acid, has been extensively used to remove formation damage in sandstone reservoirs; however, many problems may occur during stimulation treatments with this acid. To overcome many of these challenges, a phosphonic-based HF acid system has been used as an alternative to mud acid. However, very-limited research has been performed to investigate the interactions of phosphonic-based HF acid with clay minerals in sandstone reservoirs. In this study, a phosphonic-based HF acid system with two HF concentrations (1.5 and 3 wt%) was used to evaluate the solubility of various clay minerals (kaolinite, bentonite, chlorite, and illite) as a function of time and temperature. Scanning electron microscopy and energy-dispersive X-ray spectroscopy (EDS) were used to identify of the reaction products. The pH of the solutions was measured by use of an HF-resistant electrode. The concentrations of key cations in the supernatant were analyzed by use of inductively coupled plasma optical emission spectrometry. The 19F, 31P, and 27Al liquid nuclear-magnetic-resonance (NMR) spectroscopy experiments were used for the first time to evaluate the reaction of this specific phosphonic-based acid with clay minerals. Coreflood experiments on Berea sandstone cores were conducted at 300°F and a flow rate of 2 cm3/min by use of full-strength phosphonic-based HF acid (3 wt% of HF) and mud acid (12 wt% of HCl and 3 wt% of HF). No aluminum fluoride (AlF3) precipitate was identified by EDS and X-ray-diffraction analyses of the solid samples after kaolinite, bentonite, and illite reacted with full-strength phosphonic-based HF acid. Large amounts of AlF3 were noticed in the chlorite samples after being treated with a full-strength phosphonic-based HF acid. The concentration of soluble silicon decreases in the spent acid after full-strength phosphonic-based HF acid reacted with clay minerals at 302°F. This indicated a secondary reaction that occurred at high temperatures, decreasing the ratio of silicon/aluminum. This result was further confirmed by the 19F NMR results at high temperature. The 19F NMR results obtained after the high-temperature reaction showed that HF acid in the full-strength phosphonic-based-HF acid solution was completely consumed in 30 minutes when it reacted with clay minerals at a weight ratio of 10:1 at 302°F. Coreflood tests showed significant permeability improvement to Berea sandstone when using full-strength phosphonic-based HF acid compared with regular mud acid.

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25

Harris, Robin K., Lawrence H. Merwin, and Gerhard Hägele. "Salts of Phosphonic Acid Derivatives: Illustrative Examples of Solid State NMR Spectroscopy." Zeitschrift für Naturforschung B 44, no. 11 (November 1, 1989): 1407–13. http://dx.doi.org/10.1515/znb-1989-1115.

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High-resolution solid state 13C, 23Na and 31P NMR data have been obtained for the acid form and for several salts of the phosphonic acids: ethane-1,2-diphosphonic acid, ethane-1-hydroxy-1,1-diphosphonic acid (HEDP), and 3-amino-1-hydroxypropane-1,1-diphosphonic acid. The data provide evidence by which sample purity and crystallinity may be examined and from which the size of the asymmetric unit may be determined. In the case of the sodium salts of ethane-1,2-diphosphonic acid, the 31P and 23Na spectra provide evidence of possible motion or bond fluctionality for the phosphonic acid group.

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26

Peyman, Anusch, Eugen Uhlmann, Konrad Wagner, Sascha Augustin, Gerhard Breipohl, David W. Will, Andrea Schäfer, and Holger Wallmeier. "Phosphonic Ester Nucleic Acids(PHONAs): Oligonucleotide Analogues with an Achiral Phosphonic Acid Ester Backbone." Angewandte Chemie International Edition in English 35, no. 22 (December 1996): 2636–38. http://dx.doi.org/10.1002/anie.199626361.

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27

Tabcheh, M., L. Pappalardo, M. L. Roumestant, and Ph Viallefont. "Neuroexcitatory amino acids: phosphonic analogue of kainic acid." Amino Acids 2, no. 1-2 (1992): 191–93. http://dx.doi.org/10.1007/bf00806089.

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28

Müller, B., and I. Förster. "Derivatives of phosphoric and phosphonic acid as corrosion inhibitors for zinc pigments." Corrosion Science 38, no. 7 (July 1996): 1103–8. http://dx.doi.org/10.1016/0010-938x(96)00005-4.

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29

Joswig, Jan-Ole, Sandrine Hazebroucq, and Gotthard Seifert. "Properties of the phosphonic-acid molecule and the proton transfer in the phosphonic-acid dimer." Journal of Molecular Structure: THEOCHEM 816, no. 1-3 (August 2007): 119–23. http://dx.doi.org/10.1016/j.theochem.2007.04.008.

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30

Czech, Bronislaw P., Dhimant H. Desai, Jacek Koszuk, Anna Czech, David A. Babb, Thomas W. Robison, and Richard A. Bartsch. "Synthesis of lipophilic crown ethers with pendant phosphonic acid or phosphonic acid monoethyl ester groups." Journal of Heterocyclic Chemistry 29, no. 4 (July 1992): 867–75. http://dx.doi.org/10.1002/jhet.5570290433.

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31

Trzepizur, Damian, Anna Brodzka, Dominik Koszelewski, and Ryszard Ostaszewski. "Selective Esterification of Phosphonic Acids." Molecules 26, no. 18 (September 17, 2021): 5637. http://dx.doi.org/10.3390/molecules26185637.

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Here, we report straightforward and selective synthetic procedures for mono- and diesterification of phosphonic acids. A series of alkoxy group donors were studied and triethyl orthoacetate was found to be the best reagent as well as a solvent for the performed transformations. An important temperature effect on the reaction course was discovered. Depending on the reaction temperature, mono- or diethyl esters of phosphonic acid were obtained exclusively with decent yields. The substrate scope of the proposed methodology was verified on aromatic as well as aliphatic phosphonic acids. The designed method can be successfully applied for small- and large-scale experiments without significant loss of selectivity or reaction yield. Several devoted experiments were performed to give insight into the reaction mechanism. At 30 °C, monoesters are formed via an intermediate (1,1-diethoxyethyl ester of phosphonic acid). At higher temperatures, similar intermediate forms give diesters or stable and detectable pyrophosphonates which were also consumed to give diesters. 31P NMR spectroscopy was used to assign the structure of pyrophosphonate as well as to monitor the reaction course. No need for additional reagents and good accessibility and straightforward purification are the important aspects of the developed protocols.

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32

Trinchera, Alessandra, Bruno Parisi, Valentina Baratella, Giancarlo Roccuzzo, Ivano Soave, Carlo Bazzocchi, Daniele Fichera, et al. "Assessing the Origin of Phosphonic Acid Residues in Organic Vegetable and Fruit Crops: The Biofosf Project Multi-Actor Approach." Agronomy 10, no. 3 (March 19, 2020): 421. http://dx.doi.org/10.3390/agronomy10030421.

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Recently, on the EU market, phosphonic acid residues were detected in many organic goods, although fosetyl-derivates and phosphite salts are not allowed by Reg. EC n. 889/2009. The BIOFOSF project “Solving phosphite issue in organic fruit and horticultural crops” aimed at verifying whether the phosphonic acid contamination could be due to unproper use of fertilizers/plant protection products by organic farmers, or to the plant’s ability to self-produce it spontaneously. Applying a participative approach, field case-studies on potato, rocket lettuce, and pears were carried out (organic vs. integrated systems). The ethyl-phosphonic acid and phosphonic acid were determined in soil, tubers, leaves, fruits, tree woody organs, used fertilizers, and plant protection products to correlate them to the applied farming management. Tested crops were not able to self-synthetize phosphonic acid, being its detection due to: (i) external inputs not allowed in organic farming; (ii) fertilizers/plant protection products allowed in organic farming, contaminated by fosetyl or phosphite. In addition, it was found that tree crops can stock the phosphite in their woody organs, then translocate it from branches to leaves and fruits over time. Regression models applied to field data showed that fruit trees decontamination could take more than 5 years, depending on the starting value of phosphonic acid contamination, useful to define the phosphite maximum residue limit in organic fruit crops.

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33

Sebah, Majda, Sai P. Maddala, Peter Haycock, Alice Sullivan, Harold Toms, and John Wilson. "New phosphonic acid polysilsesquioxane mild solid acid catalysts." Journal of Molecular Catalysis A: Chemical 374-375 (August 2013): 59–65. http://dx.doi.org/10.1016/j.molcata.2013.03.021.

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34

Schilling, Marcia L., Howard E. Katz, Francis M. Houlihan, Janet M. Kometani, Susan M. Stein, and Omkaram Nalamasu. "Photogenerated Acid-Catalyzed Formation of Phosphonic/Phosphoric Acids by Deprotection of Esters in Polymer Films." Macromolecules 28, no. 1 (January 1995): 110–15. http://dx.doi.org/10.1021/ma00105a014.

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35

Kiss, Nóra Zsuzsa, and György Keglevich. "Direct esterification of phosphinic and phosphonic acids enhanced by ionic liquid additives." Pure and Applied Chemistry 91, no. 1 (January 28, 2019): 59–65. http://dx.doi.org/10.1515/pac-2018-1008.

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Abstract The beneficial combination of microwave (MW) and ionic liquid (IL) additives was exploited in the direct esterification of a series of acyclic phosphinic and phosphonic acids giving rise to phenyl-H-phosphinates/methyl-phenylphosphinates/diphenylphosphinates and phenylphosphonic mono- and diesters, respectively. The latter is the first example for the direct esterification of a phosphonic acid.

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36

Fuchs, Stefan, and Hubert Schmidbaur. "Phosphonic Acid Anhydrides [RPO2]n: Oligomerization and Structure." Zeitschrift für Naturforschung B 50, no. 6 (June 1, 1995): 855–58. http://dx.doi.org/10.1515/znb-1995-0601.

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The phosphonic acid anhydrides of the general formula [RPO2]n have been prepared with R = Me, Et, i-Pr, t-Bu, and Ph from the corresponding phosphonic acids and their chlorides and esters. Mass spectrometric data indicate that the trimers are the dominant oligomers for all five systems. According to their NMR spectra, the methyl and t-butyl compounds have a symmetrical (C3v) structure with equivalent RP groups, while the ethyl, i-propyl and phenyl homologues have the Cs structure with non-equivalent PR groups in the ratio 1:2.

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37

Schlichting, Gregory J., James L. Horan, and Andrew M. Herring. "Phosphonic Acid Based Proton Exchange Membrane." ECS Transactions 33, no. 1 (December 17, 2019): 777–81. http://dx.doi.org/10.1149/1.3484572.

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38

Stokes, Kristoffer K., Karine Heuzé, and Richard D. McCullough. "New Phosphonic Acid Functionalized, Regioregular Polythiophenes." Macromolecules 36, no. 19 (September 2003): 7114–18. http://dx.doi.org/10.1021/ma034639+.

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39

Chadha, R. K., and G. Ösapay. "(S)-[1-(Benzyloxycarbonylamino)ethyl]phosphonic Acid." Acta Crystallographica Section C Crystal Structure Communications 51, no. 11 (November 15, 1995): 2340–42. http://dx.doi.org/10.1107/s0108270195004355.

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40

Davis, Lindsey O., William F. M. Daniel, and Suzanne L. Tobey. "Phosphonic acid catalyzed synthesis of pyrazolidines." Tetrahedron Letters 53, no. 5 (February 2012): 522–25. http://dx.doi.org/10.1016/j.tetlet.2011.11.083.

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41

Kibardina, L. K., M. A. Pudovik, R. M. Kamalov, and A. N. Pudovik. "Functional derivatives of (bromomethyl)phosphonic acid." Russian Journal of General Chemistry 74, no. 8 (August 2004): 1168–70. http://dx.doi.org/10.1007/s11176-005-0131-3.

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42

Opper, Kathleen L., Dilyana Markova, Markus Klapper, Klaus Müllen, and Kenneth B. Wagener. "Precision Phosphonic Acid Functionalized Polyolefin Architectures." Macromolecules 43, no. 8 (April 27, 2010): 3690–98. http://dx.doi.org/10.1021/ma902659y.

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43

Kaname, Mamoru, Kazuo Yoshinaga, Yasushi Arakawa, and Shigeyuki Yoshifuji. "Synthesis of Hexahydropyridazine-3-phosphonic Acid." CHEMICAL & PHARMACEUTICAL BULLETIN 52, no. 1 (2004): 160–62. http://dx.doi.org/10.1248/cpb.52.160.

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44

Hu, Hairong, Chuanfang Zhu, and Juan Fu. "Synthesis of phosphonic acid containing thiadiazole." Heteroatom Chemistry 19, no. 2 (March 2008): 140–43. http://dx.doi.org/10.1002/hc.20395.

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45

Kim, Sung-Kon. "Polybenzimidazole and Phosphonic Acid Groups-Functionalized Polyhedral Oligomeric Silsesquioxane Composite Electrolyte for High Temperature Proton Exchange Membrane." Journal of Nanomaterials 2016 (2016): 1–7. http://dx.doi.org/10.1155/2016/2954147.

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Here, we report composite membrane consisting of poly[2,2′-(m-phenylene)-5,5′-(bibenzimidazole)] (PBI) and polyhedral oligomeric silsesquioxane functionalized with phosphonic acid groups (PO(OH)2-POSS) for high temperature proton exchange membrane. ~7 phosphonic acid groups are incorporated into the phenyl rings of POSS via bromination in a high yield (~93%), followed by substitution of the bromine elements by phosphonate ester groupsviaa Pd(0) catalyzed P–C coupling reaction. Phosphonic acid groups are formed by the hydrolysis of the phosphonate ester groups in hydrobromic acid solution. At a 50 wt% of PA content in the membranes, PBI/PO(OH)2-POSS composite membrane shows larger proton conductivity of 3.2 × 10−3 S cm−1than 2.8 × 10−3 S cm−1of PBI membrane at 150°C and anhydrous conditions, owing to the multiple phosphonic acid groups of PO(OH)2-POSS that can function as proton transport medium at high temperature and low humidity conditions.

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46

Forchetta, Mattia, Valeria Conte, Giulia Fiorani, Pierluca Galloni, and Federica Sabuzi. "A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones." Organics 2, no. 2 (June 3, 2021): 107–17. http://dx.doi.org/10.3390/org2020010.

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Owing to the attractiveness of organic phosphonic acids and esters in the pharmacological field and in the functionalization of conductive metal-oxides, the research of effective synthetic protocols is pivotal. Among the others, ω-bromoalkylphosphonates are gaining particular attention because they are useful building blocks for the tailored functionalization of complex organic molecules. Hence, in this work, the optimization of Michaelis–Arbuzov reaction conditions for ω-bromoalkylphosphonates has been performed, to improve process sustainability while maintaining good yields. Synthesized ω-bromoalkylphosphonates have been successfully adopted for the synthesis of new KuQuinone phosphonate esters and, by hydrolysis, phosphonic acid KuQuinone derivatives have been obtained for the first time. Considering the high affinity with metal-oxides, KuQuinones bearing phosphonic acid terminal groups are promising candidates for biomedical and photo(electro)chemical applications.

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47

Tong, Jian-Wei, Li-Fang Ma, Deng-Ke Cao, Yi-Zhi Li, and Li-Min Zheng. "[(1H-Benzimidazol-2-ylmethyl)iminodimethylene]diphosphonic acid dihydrate." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 9, 2006): o2694—o2696. http://dx.doi.org/10.1107/s1600536806019763.

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The title compound, C9H15O6N3P2·2H2O, contains two phosphonic acid groups and one benzimidazole group connected by an N(CH2–)3 group. One of the benzimidazole N atoms and two phosphonic acid O atoms of each PO3 group are protonated. Extensive hydrogen-bonding interactions, as well as π–π stacking interactions, are found between the molecules, leading to a three-dimensional supramolecular network structure.

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48

Baumgartner, Yann, Y. Maximilian Klein, Edwin C. Constable, Catherine E. Housecroft, and Markus Willgert. "Cyanoacrylic- and (1-cyanovinyl)phosphonic acid anchoring ligands for application in copper-based dye-sensitized solar cells." RSC Advances 6, no. 89 (2016): 86220–31. http://dx.doi.org/10.1039/c6ra20375b.

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Replacing phosphonic acid by (1-cyanovinyl)phosphonic acid anchors in heteroleptic bis(diimine)copper(i) dyes in DSCs gives a gain in J_SC; a dye with a bpy-based anchor gives improved performance over one with a phen-based anchor.

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49

Bravo-Altamirano, Karla, and Jean-Luc Montchamp. "A novel approach to phosphonic acids from hypophosphorous acid." Tetrahedron Letters 48, no. 33 (August 2007): 5755–59. http://dx.doi.org/10.1016/j.tetlet.2007.06.090.

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50

Cabal, Jiří, Jiří Kassa, and Jiří Patočka. "Inhibition of Plasma Cholinesterase by O-Alkylfluorophosphonates." Collection of Czechoslovak Chemical Communications 62, no. 3 (1997): 521–26. http://dx.doi.org/10.1135/cccc19970521.

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Inhibition of plasma cholinesterase by three methylfluorophosphonates (MFF), sarin, soman and cyclosin, and by the products of their hydrolysis and alcoholysis was examined. Inhibition by phosphonic acids and by methyl esters derived from MFF was purely competitive while that by MFF was irreversible. The rate of phosphorylation of cholinesterase by MFF differs, depending on the structure of the alkoxy group in the MFF and decreases in the sequence soman-sarin-cyclosin. The affinity values of MFF, phosphonic acids and methyl esters of phosphonic acid for cholinesterase are comparable. The in vitro kinetic parameters suggest that plasma cholinesterase might act as a natural detoxicating agent in cases of poisoning with the above inhibitors of acetylcholinesterase.

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