Synthesis of a lariat ether having a phosphinic acid functional group and the crystal structure of its sodium(1+) complex: sodium sym-[(dibenzo-14-crown-4-oxy)methyl]phenylphosphinate dihydrate diethanolate

1988 ◽  
Vol 27 (10) ◽  
pp. 1787-1790 ◽  
Author(s):  
Richard A. Sachleben ◽  
John H. Burns ◽  
George M. Brown
Keyword(s):  
Crystal Structure ◽  
Functional Group ◽  
Phosphinic Acid ◽  
Lariat Ether ◽  
Acid Functional Group

scholarly journals Phosphonic acid: preparation and applications

2017 ◽  
Vol 13 ◽  
pp. 2186-2213 ◽  
Author(s):  
Charlotte M Sevrain ◽  
Mathieu Berchel ◽  
Hélène Couthon ◽  
Paul-Alain Jaffrès
Keyword(s):  
Phosphonic Acid ◽  
Functional Group ◽  
Phosphinic Acid ◽  
Phosphorous Acid ◽  
Direct Methods ◽  
Phosphonic Acids ◽  
Research Fields ◽  
Dialkyl Phosphonates ◽  
Review Reports ◽  
Acid Functional Group

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.

scholarly journals Crystal structure of tetrakis[μ-3-carboxy-1-(1,2,4-triazol-4-yl)adamantane-κ2 N 1:N 2]tetrafluoridodi-μ2-oxido-dioxidodisilver(I)divanadium(V) tetrahydrate

2019 ◽  
Vol 75 (6) ◽  
pp. 808-811 ◽  
Author(s):  
Ganna A. Senchyk ◽  
Andrey B. Lysenko ◽  
Eduard B. Rusanov ◽  
Kostiantyn V. Domasevitch
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Functional Group ◽  
Crystal Packing ◽  
Water Molecules ◽  
Coordination Environment ◽  
Trigonal Bipyramidal ◽  
Distorted Trigonal Bipyramidal Coordination ◽  
Acid Functional Group ◽  
Distorted Trigonal Bipyramidal

The crystal structure of the title molecular complex, [Ag2{VO2F2}2(C13H17N3O2)4]·4H2O, supported by the heterofunctional ligand tr-ad-COOH [1-(1,2,4-triazol-4-yl)-3-carboxyadamantane] is reported. Four 1,2,4-triazole groups of the ligand link two AgI atoms, as well as AgI and VV centres, forming the heterobimetallic coordination cluster {AgI 2(VVO2F2)2(tr)4}. VV exists as a vanadium oxofluoride anion and possesses a distorted trigonal–bipyramidal coordination environment [VO2F2N]. A carboxylic acid functional group of the ligand stays in a neutral form and is involved in hydrogen bonding with solvent water molecules and VO2F2 − ions of adjacent molecules. The extended hydrogen-bonding network is responsible for the crystal packing in the structure.

GRX: a program to search the CSD for functional group exchanges

2005 ◽  
Vol 38 (4) ◽  
pp. 694-696 ◽  
Author(s):  
Jacco van de Streek ◽  
Sam Motherwell
Keyword(s):  
Crystal Structure ◽  
Crystal Structures ◽  
Functional Group ◽  
Cambridge Structural Database ◽  
Structural Database

In order to establish the effect of exchanging one functional group by another on the crystal structure, one would like to be able to search the Cambridge Structural Database for all pairs of crystal structures where this substitution has been made. A program calledGRX(group exchange) was written for that purpose.

scholarly journals Evaluation of the cyclopentane-1,2-dione as a potential bio-isostere of the carboxylic acid functional group

2014 ◽  
Vol 24 (17) ◽  
pp. 4171-4175 ◽  
Author(s):  
Carlo Ballatore ◽  
Bryant Gay ◽  
Longchuan Huang ◽  
Katie Herbst Robinson ◽  
Michael J. James ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Functional Group ◽  
Acid Functional Group

Melaminium (2-carboxyethyl)(phenyl)phosphinate monohydrate

2012 ◽  
Vol 68 (9) ◽  
pp. o355-o358 ◽  
Author(s):  
Jun Xue ◽  
Cui-Cui Zhao ◽  
Zi-Yi Du
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Electrostatic Interactions ◽  
Large Scale ◽  
Phosphinic Acid ◽  
Thick Layer ◽  
Stacking Interactions ◽  
Two Dimensional ◽  
Compound C ◽  
Secondary Building Units

Cocrystallization of melamine (1,3,5-triazine-2,4,6-triamine, ma) with (2-carboxyethyl)(phenyl)phosphinic acid (H2L) from water affords the title compound, C3H7N6+·C9H10O4P−·H2O or (maH)(HL)·H2O, (I). The phosphinic acid H atom of each H2Lmolecule is transferred to a melamine molecule. Structural analysis reveals that there are two types of secondary building units in the crystal structure, namely cationic [(maH+)2]∞ribbons and anionic {[(HL)2(H2O)2]2−}∞layers, the combination of which through hydrogen-bond and electrostatic interactions, generates a large-scale two-dimensional layered structure. The thick layer is sandwich-like, with the central [(maH+)2]∞ribbons being further stabilized by π–π stacking interactions. It is also worthy of note that two conformational isomericR65(24) hydrogen-bond ring motifs can be identified in the {[(HL)2(H2O)2]2−}∞layer.

scholarly journals Crystal Structure of the ECH2 Catalytic Domain of CurF from Lyngbya majuscula

2007 ◽  
Vol 282 (49) ◽  
pp. 35954-35963 ◽  
Author(s):  
Todd W. Geders ◽  
Liangcai Gu ◽  
Jonathan C. Mowers ◽  
Haichuan Liu ◽  
William H. Gerwick ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Functional Group ◽  
Catalytic Domain ◽  
Acyl Carrier Protein ◽  
Cyclopropane Ring ◽  
Chemical Diversity ◽  
Site Directed Mutagenesis ◽  
Lyngbya Majuscula ◽  
Multifunctional Protein ◽  
Curacin A

Curacin A is a mixed polyketide/nonribosomal peptide possessing anti-mitotic and anti-proliferative activity. In the biosynthesis of curacin A, the N-terminal domain of the CurF multifunctional protein catalyzes decarboxylation of 3-methylglutaconyl-acyl carrier protein (ACP) to 3-methylcrotonyl-ACP, the postulated precursor of the cyclopropane ring of curacin A. This decarboxylase is encoded within an “HCS cassette” that is used by several other polyketide biosynthetic systems to generate chemical diversity by introduction of a β-branch functional group to the natural product. The crystal structure of the CurF N-terminal ECH2 domain establishes that the protein is a crotonase superfamily member. Ala78 and Gly118 form an oxyanion hole in the active site that includes only three polar side chains as potential catalytic residues. Site-directed mutagenesis and a biochemical assay established critical functions for His240 and Lys86, whereas Tyr82 was nonessential. A decarboxylation mechanism is proposed in which His240 serves to stabilize the substrate carboxylate and Lys86 donates a proton to C-4 of the acyl-ACP enolate intermediate to form the Δ2 unsaturated isopentenoyl-ACP product. The CurF ECH2 domain showed a 20-fold selectivity for ACP-over CoA-linked substrates. Specificity for ACP-linked substrates has not been reported for any other crotonase superfamily decarboxylase. Tyr73 may select against CoA-linked substrates by blocking a contact of Arg38 with the CoA adenosine 5′-phosphate.

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