Preparation and Crystal Structure of the Potentially Tridentate Substituted Phenoxyacetic Acid (2-Benzoyl-5-methoxyphenoxy)acetic Acid and Its Complex Adduct With Sodium

1995 ◽  
Vol 48 (4) ◽  
pp. 869 ◽  
Author(s):  
G Smith ◽  
EJ Oreilly ◽  
SA See ◽  
KA Byriel ◽  
CHL Kennard
Keyword(s):  
Crystal Structure ◽  
Acetic Acid ◽  
Carboxy Group ◽  
Intramolecular Hydrogen Bonding ◽  
Ligand Molecule ◽  
Phenoxyacetic Acid ◽  
X Ray Diffraction ◽  
X Ray ◽  
Intramolecular Hydrogen ◽  
Hydrogen Bonded

The ring-substituted phenoxyacetic acid (2-benzoyl-5-methoxyphenoxy)acetic acid (HL) (3) and its complex adduct dimer (4) with sodium, [Na2(L)2(HL)2].2HL, have been synthesized and their structures determined by X-ray diffraction. The acid (3) does not have the usual cyclic hydrogen-bonded dimer association, but instead has three-centre intramolecular hydrogen bonding between the carboxyl proton and both the ether and keto oxygens [O---O, 2.602(3), 2.711(3) Ǻ respectively]. Each sodium in the centrosymmetric complex dimer (4) is seven-coordinate [Na-O, 2.313(5)-2.612(5) Ǻ], involving the 'inner' three oxygens of both a protonated and an ionic ligand molecule. In addition, one of these carboxyl oxygens forms a bridge to the inversion-related sodium, while the uncoordinated carboxyl oxygen is hydrogen-bonded to a protonated carboxy group [O---O, 2.464(8) Ǻ]. The molecules of the lattice acid have only one hydrogen-bonded association with the second uncoordinated carboxy group in the dimer [O---O, 2.513(7) Ǻ].

Metal Phenoxyalkanoic Acid Interactions. XXV. The Crystal Structures of (2-Formyl-6-Methoxyphenoxy)Acetic Acid and Its Zinc(II) Complex and the Lithium, Zinc(II) and Cadmium(II) Complexes of (2-Chlorophenoxy)Acetic Acid

1987 ◽  
Vol 40 (7) ◽  
pp. 1147 ◽  
Author(s):  
EJ Oreilly ◽  
G Smith ◽  
CHL Kennard ◽  
TCW Mak
Keyword(s):  
Acetic Acid ◽  
Crystal Structures ◽  
Free Acid ◽  
Rotational Symmetry ◽  
Carboxyl Groups ◽  
X Ray Diffraction ◽  
X Ray ◽  
The Third ◽  
Planar Complex ◽  
Hydrogen Bonded

The crystal structures of (2-formyl-6-methoxyphenoxy)acetic acid (1), diaquabis [(2-formyl-6-methoxyphenoxy) acetato ]zinc(11) (2), tetraaquabis [(2-chlorophenoxy) acetato ]zinc(11) (3), triaquabis [(2-chlorophenoxy) acetato ]cadmium(11) dihydrate (4) and lithium (2-chloro- phenoxy )acetate 1.5 hydrate (5) have been determined by X-ray diffraction. The acid (1) forms centrosymmetric hydrogen-bonded cyclic dimers [O…0, 2.677(6) �] which are non-planar. Complex (2) is six-coordinate with two waters [Zn- Ow , 1.997(2) �] and four oxygens from two asymmetric bidentate carboxyl groups [Zn-O, 2.073, 2.381(2) �] completing a skew trapezoidal bipyramidal stereochemistry. Complex (5) is also six-coordinate but is octahedral, with two trans-related unidentate carboxyl oxygens [mean Zn-O, 2.134(9) �] and four waters [mean Zn-O, 2.081(9) �]. The seven-coordinate complex (4) has crystallographic twofold rotational symmetry relating two :symmetric bidentate acid ligands [ Cd -O, 2.26, 2 48(:) �] and two waters [ Cd -O, 2.34(2) �] while the third water lies on this axis [ Cd -O, 2.27(2) �]. In contrast to the monomers (2)-(4), complex (5) is polymeric with tetrahedral lithium coordinated to one water and three carboxylate oxygens [mean Li-0, 1.95(1) �]. The essential conformation of the free acid is retained in complexes (2), (3) and (4) but in (5), it is considerably changed.

scholarly journals Synthesis and Complexation Properties of 2-Hydroxy-5-methoxyphenylphosphonic Acid (H3L1). Crystal Structure of the [Cu(H2L1)2(Н2О)2] Complex

2021 ◽  
Vol 91 (11) ◽  
pp. 2176-2186
Author(s):  
G. S. Tsebrikova ◽  
Yu. I. Rogacheva ◽  
I. S. Ivanova ◽  
A. B. Ilyukhin ◽  
V. P. Soloviev ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Methoxy Group ◽  
Protonation Constants ◽  
Water Molecules ◽  
X Ray Diffraction ◽  
X Ray ◽  
The Stability ◽  
Intramolecular Hydrogen ◽  
Oxygen Atoms

Abstract 2-Hydroxy-5-methoxyphenylphosphonic acid (H3L1) and the complex [Cu(H2L1)2(H2O)2] were synthesized and characterized by IR spectroscopy, thermogravimetry, and X-ray diffraction analysis. The polyhedron of the copper atom is an axially elongated square bipyramid with oxygen atoms of phenolic and of monodeprotonated phosphonic groups at the base and oxygen atoms of water molecules at the vertices. The protonation constants of the H3L1 acid and the stability constants of its Cu2+ complexes in water were determined by potentiometric titration. The protonation constants of the acid in water are significantly influenced by the intramolecular hydrogen bond and the methoxy group. The H3L1 acid forms complexes CuL‒ and CuL24‒ with Cu2+ in water.

Synthesis, Characterization, and Crystal Structure of Several Novel Acidic Ionic Liquids: 1-ethyl-2-alkyl-benzimidazolium Tetra-Fluoroborate

2013 ◽  
Vol 457-458 ◽  
pp. 139-143 ◽  
Author(s):  
Ming Tian Wang ◽  
Chang Ping Pan ◽  
Wei Peng Gai ◽  
Xiao Xia Lv ◽  
Min Gang Zhai ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Ionic Liquid ◽  
Acetic Acid ◽  
Catalytic Activity ◽  
Lamellar Structure ◽  
X Ray Diffraction ◽  
X Ray ◽  
Acidic Ionic Liquid ◽  
Acidic Ionic Liquids ◽  
Good Catalytic Activity

A series of novel acidic ionic liquid: 1-ethyl-2-alkyl-benzimidazolium tetra-fluoroborate (alkyl= Et, Pr-n, Bu-n) were prepared by simple acid-based neutralization of 1-ethyl-2-alkyl-benzimidazole and tetrafluoroboric acid. The compounds were characterized by FTIR spectra, elemental analysis,1HNMR spectra and thermogravimetric analysis. These novel tetra-fluoroborate salts show good catalytic activity to esterification of benzyl alcohol and acetic acid. Furthermore, a crystal of ([H-ebBiBF4) was prepared with the crystal structure and determined by X-ray diffraction analysis. The molecular is of lamellar structure as mainly π electron ring is stacked interleaving between two layers. The results of cation and anion arranged orderly in pair indicate that the coulombic attraction is more dominant. Simultaneously, the weak local hydrogen bonds C-H···F exist in the molecules.

Conformational Comparisons Between Phenoxyacetic Acid Derivatives in Adducts and in the Free Form

1999 ◽  
Vol 52 (7) ◽  
pp. 695 ◽  
Author(s):  
Graham Smith ◽  
Catherine J. Cooper ◽  
Veena Chauhan ◽  
Daniel E. Lynch ◽  
Simon Parsons ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Single Crystal ◽  
Free Acid ◽  
Molecular Complexes ◽  
The Other ◽  
Free Form ◽  
Phenoxyacetic Acid ◽  
X Ray Diffraction ◽  
X Ray ◽  
Dichlorophenoxy Acetic Acid

Six molecular complexes containing the herbicidally active (2,4-dichlorophenoxy)acetic acid (2,4-d) and (2,4,5-trichlorophenoxy)acetic acid (2,4,5-t) have been prepared and studied by using single-crystal X-ray diffraction techniques. These adduct structures are 2,4-d with 4,4′-dipyridine (2 : 1 complex), and 2,4,5-t with respectively 5-nitroquinoline (1 : 1), 4,4′-dipyridine (2 : 1), 2-amino-2-thiazoline (1 : 1), 2-aminobenzothiazole (1 : 1) and 2-amino-5-ethyl-1,3,4-thiadiazole (1 : 1). The conformations of the phenoxyacetic acid molecules were found to be either synclinal (in three cases) or antiperiplanar (in the other three cases). A general review is also made about the conformational aspects of previously reported adducts of phenoxyacetic acid derivatives and how they compare to their free acid structures.

Molecular Cocrystals of Carboxylic Acids. XV. Preparation and Characterization of Heterocyclic Base Adducts With a Series of Carboxylic Acids, and the Crystal Structures of the Adducts of 2-Aminopyrimidine With 2,6-Dihydroxybenzoic Acid, 4-Aminobenzoic Acid, Phenoxyacetic Acid, (2,4-Dichlorophenoxy)acetic Acid, (3,4-Dichlorophenoxy)-acetic Acid and Salicylic Acid, and 2-Aminopyridine With 2,6-Dihydroxybenzoic Acid

1994 ◽  
Vol 47 (6) ◽  
pp. 1097 ◽  
Author(s):  
DE Lynch ◽  
G Smith ◽  
D Freney ◽  
KA Byriel ◽  
CHL Kennard
Keyword(s):  
Acetic Acid ◽  
Salicylic Acid ◽  
Carboxylic Acids ◽  
Phenoxyacetic Acid ◽  
Aminobenzoic Acid ◽  
X Ray Diffraction ◽  
Dihydroxybenzoic Acid ◽  
Heterocyclic Base ◽  
X Ray ◽  
Dichlorophenoxy Acetic Acid

The molecular adducts of the heterocyclic base 2-aminopyrimidine with the aromatic and aromatic aliphatic carboxylic acids salicylic acid, 2,6-dihydroxybenzoic acid and 4-aminobenzoic acid, phenoxyacetic acid, (2,4-dichlorophenoxy)acetic acid, and (3,4-dichlorophenoxy)acetic acid have been prepared, and their interactive modes characterized by single-crystal X-ray diffraction methods. In addition, the complexes with (4-chlorophenoxy)acetic acid, (2,3-dichlorophenoxy)acetic acid, (4-chloro-2-methylphenoxy)acetic acid and (2,4,5- trichlorophenoxy)acetic acid have been characterized by analytical methods, including infrared spectroscopy. Except for the phenoxyacetic acid adduct (2:1), all form 1:1 molecular associations in which the carboxylic acid shows a variable tendency to protonate the hetero nitrogen of the base. The 1:1 complex of 2-aminopyridine with 2,6-dihydroxybenzoic acid has also been characterized by single-crystal X-ray diffraction.

Synthesis of 2', 6'-Dihydroxychalcones by Using Tetrahydropyran-2-yl and Trialkylsilyl Protective Groups; the Crystal Structure Determination of 2',6'-Dihydroxy-2,4,6-trimethoxychalcone

1989 ◽  
Vol 42 (7) ◽  
pp. 1103 ◽  
Author(s):  
CO Miles ◽  
L Main ◽  
BK Nicholson
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Silyl Ether ◽  
X Ray ◽  
Protective Groups ◽  
Intramolecular Hydrogen ◽  
First Time ◽  
Mild Acid

Two improved general routes to 2′,6′-dihydroxychalcones are described in which the final step is protective-group removal from O 2′ under mild acid conditions. The first involves base-catalysed condensation of benzaldehydes with 2′-hydroxy-6′-tetrahydropyran-2-yloxyacetophenone, the second ring-opening of 5-hydroxyflavanones with 1,8-diazabicyclo[5.4.0]undec-7-ene in the presence of a trialkylchlorosilane to trap out the chalcone as a bis silyl ether. Chalcones prepared by the first route are 2',6'-dihydroxychalcone (1), and its 4-methoxy (2), 3,4-dimethoxy (3), 3,4,5-trimethoxy (4), and 2,4,6-trimethoxy (5) derivatives. The 4-chloro derivative (6) and the chalcone from hesperetin are prepared by the second method. .The X-ray crystal structure of 2',6'-dihydroxy-2,4,6-trimethoxychalcone (5), the first for a 2',6′-dihydroxychalcone, is reported, the hydrogen involved in intramolecular hydrogen-bonding between the carbonyl and phenolic oxygens being located for the first time for any 2'-hydroxychalcone derivative. The O 6' involved in the intramolecular hydrogen-bonding is also hydrogen-bonded intermolecularly to the hydrogen of the other (2'-)hydroxy group of a neighbouring molecule in the lattice. 13C n.m.r. data are the first reported for a series of 2',6'-dihydroxychalcones.

Molecular Cocrystals of Carboxylic Acids. XVII. Spectral Characterization of the Adducts of Triphenylphosphine Oxide With Substituted Phenoxyacetic Acids and the Crystal Structure of the 1 : 1 Adduct With (4-Chloro-2-methylphenoxy)acetic Acid

1994 ◽  
Vol 47 (7) ◽  
pp. 1401 ◽  
Author(s):  
DE Lynch ◽  
G Smith ◽  
KA Byriel ◽  
CHL Kennard ◽  
AK Whittaker ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Acetic Acid ◽  
Triphenylphosphine Oxide ◽  
X Ray Diffraction ◽  
X Ray ◽  
Acid Proton ◽  
Phosphoryl Oxygen ◽  
Phenoxyacetic Acids ◽  
Dichlorophenoxy Acetic Acid ◽  
Molecular Adducts

A series of 1:1 molecular adducts of triphenylphosphine oxide ( tppo ) with substituted phenoxyacetic acids has been prepared and characterized by using infrared, solid-state 1H and 31P n.m.r. spectroscopy, and X-ray powder diffraction methods. The crystal structure of one of these, with the herbicidally active (4-chloro-2-methylphenoxy)acetic acid ( mcpa ),[( tppo )( mcpa )], has been determined by X-ray diffraction methods. This compound is isomorphous with the tppo adduct of (2,4-dichlorophenoxy)acetic acid. The title compound has two independent and different molecular adducts in the asymmetric unit each with strong hydrogen-bonding interactions between the carboxylic acid proton and the phosphoryl oxygen of tppo [O...O, 2.579, 2.647(9)Ǻ].

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