Molecular Cocrystals of Carboxylic Acids. XXV The Utility of Urea in Structure Making with Carboxylic Acids and the Crystal Structures of a Set of Six Adducts with Aromatic Acids

1997 ◽  
Vol 50 (7) ◽  
pp. 727 ◽  
Author(s):  
Graham Smith ◽  
Katherine E. Baldry ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Hydrogen Bonding ◽  
Infrared Spectroscopy ◽  
Dicarboxylic Acid ◽  
Carboxylic Acids ◽  
Phthalic Acid ◽  
Aromatic Acids ◽  
Aminobenzoic Acid ◽  
X Ray Diffraction ◽  
X Ray ◽  
Polymeric Structures

Molecular adducts of urea with six aromatic carboxylic acids have been prepared and characterized by using X-ray diffraction methods and infrared spectroscopy. These compounds are with 5-nitrosalicylic acid [(C7H5NO5)2(CH4N2O)] (1), 3,5-dinitrosalicylic acid [(C7H4N2O7)(CH4N2O)] (2), 4-aminobenzoic acid [(C7H7NO2)2(CH4N2O)] (3), o-phthalic acid [(C8H6O4)(CH4N2O)] (4), pyrazine-2,3-dicarboxylic acid [(C4H4N2O4)(CH4N2O)] (5) and pyridine-2,6-dicarboxylic acid [(C7H5NO4)(CH4N2O)2] (6). In the majority of the adducts, all six potential interactive sites on the urea molecules are utilized in hydrogen bonding, giving polymeric structures.

Molecular Cocrystals of Carboxylic Acids. XXVI Adducts of the Amino-Substituted Benzoic Acids with Nitroaromatic Lewis Bases: the Influence of Associative Polyfunctional Substituents on Self-Assembly of Molecules in Cocrystallization Processes

1997 ◽  
Vol 50 (10) ◽  
pp. 977 ◽  
Author(s):  
Daniel E. Lynch ◽  
Graham Smith ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Hydrogen Bonding ◽  
Infrared Spectroscopy ◽  
Self Assembly ◽  
Benzoic Acids ◽  
Aminobenzoic Acid ◽  
X Ray Diffraction ◽  
X Ray ◽  
Lewis Bases ◽  
Aminobenzoic Acids ◽  
Substituted Benzoic Acids

A series of molecular adducts of the isomeric aminobenzoic acids with the nitro-substituted Lewis bases 2-chloro-5-nitropyridine, 5-nitroquinoline and 5-nitroisoquinoline has been prepared and characterized by using infrared spectroscopy and X-ray powder diffraction, and in four cases by single-crystal X-ray diffraction methods. These four compounds are the adducts of 3-aminobenzoic acid with 5-nitroquinoline [(C7H7NO2)(C9H6N2O2)], 4-aminobenzoic acid with 5-nitroquinoline [(C7H7NO2)2(C9H6N2O2)], 2-aminobenzoic acid with 5-nitroisoquinoline [(C7H7NO2)(C9H6N2O2)] and 4-aminobenzoic acid with 5-nitroisoquinoline [(C7H7N2O2)(C9H6N2O2)]. Other compounds described are the (1 : 1) adducts of 4-aminobenzoic acid with 2-chloro-5-nitropyridine, and 2-aminobenzoic acid with 5-nitroquinoline. All adducts involve hydrogen-bonding network associations while in none of the examples is any proton transfer involved.

Molecular Cocrystals of Carboxylic Acids. XXVIII. Nitro-Substituted Carboxylic Acids with Lewis Bases: the Crystal Structures of the Adducts of 3,5-Dinitrobenzoic Acid with N-Methylaniline (1 : 1), (4-Nitrophenyl)acetic Acid with Cyclohexane-1,4-diamine (2 : 1), and 5-Nitrosalicylic Acid with 2-Imidazolidone (2 : 1)

1998 ◽  
Vol 51 (2) ◽  
pp. 159 ◽  
Author(s):  
Graham Smith ◽  
Daniel E. Lynch ◽  
Raymond C. Bott
Keyword(s):  
Acetic Acid ◽  
Infrared Spectroscopy ◽  
Carboxylic Acid ◽  
Proton Transfer ◽  
Crystal Structures ◽  
Carboxylic Acids ◽  
Aromatic Acids ◽  
X Ray Diffraction ◽  
X Ray ◽  
Lewis Bases

A number of molecular adducts of nitro-substituted aromatic acids with Lewis bases have been prepared and characterized by infrared spectroscopy and in three cases by X-ray diffraction methods. These three compounds are the adducts of: 3,5-dinitrobenzoic acid (dnba) with N-methylaniline (nma), [(dnba)-(nma)+] (1); (4-nitrophenyl)acetic acid (4-npa) with cyclohexane-1,4-diamine (dach), [(4-npa)22-(dach)2+] (4); 5-nitrosalicylic acid (5-nsa) with 2-imidazolidone (idaz), [(5-nsa)2(idaz)] (5). Other compounds are the adducts of 3,5-dinitrobenzoic acid with 2,6-dimethylpyridine (dmp), [(dnba)(dnba)-(dmp)+] (2), and with 1-methylpyrrole-2-carboxylic acid (cmp), [(dnba)-(cmp)+] (3). Compounds (1) and (3) have 1 : 1 stoichiometry, while (2), (4) and (5) are 2 : 1 adducts. Proton transfer occurs in most examples [complex (5) is the exception].

Molecular Cocrystals of Carboxylic Acids. XIX. The Crystal Structures of Two Adducts of 3-Aminobenzoic Acid With 3,5-Dinitrobenzoic Acid: the 1:1 and the 2:2 Hydrate Cocrystals

1994 ◽  
Vol 47 (9) ◽  
pp. 1789 ◽  
Author(s):  
DE Lynch ◽  
G Smith ◽  
KA Byriel ◽  
CHL Kennard
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Amine Group ◽  
Aromatic Acids ◽  
Aminobenzoic Acid ◽  
X Ray Diffraction ◽  
Aromatic Carboxylic Acid ◽  
X Ray ◽  
Lattice Water ◽  
Hydrate Complex

Two cocrystalline molecular adducts of 3-aminobenzoic acid (3-aba) with the aromatic carboxylic acid 3,5-dinitrobenzoic acid (dnba), [(3-aba)(dnba)](1) and [(3-aba)2(dnba)2(H2O)] (2), have been prepared and their hydrogen-bonding associations determined by means of single-crystal X-ray diffraction. Complex (1) is similar to known 1:1 complexes of 4-aminobenzoic acid with other aromatic acids, with protonation of the amine group and carboxylic acid-carboxylate hydrogen-bonding associations. However, the 2:2 hydrate complex (2) has only one hetero-pair involved in proton transfer, the other remaining neutral. With both compounds there is an extensive hydrogen-bonding network involving all substituent functional groups as well as the lattice water in compound (2).

Molecular Cocrystals of Carboxylic Acids. XIV. The Crystal Structures of the Adducts of Pyrazine-2,3-dicarboxylic Acid With 4-Aminobenzoic Acid, 3-Hydroxypyridine and 3-Amino-1,2,4-triazole

1994 ◽  
Vol 47 (2) ◽  
pp. 309 ◽  
Author(s):  
DE Lynch ◽  
G Smith ◽  
KA Byriel ◽  
CHL Kennard ◽  
AK Whittaker
Keyword(s):  
Hydrogen Bonding ◽  
Dicarboxylic Acid ◽  
Crystal Structures ◽  
Molecular Hydrogen ◽  
Triphenylphosphine Oxide ◽  
Spectroscopic Methods ◽  
Aminobenzoic Acid ◽  
X Ray Diffraction ◽  
X Ray ◽  
Hydrogen Bonding Interactions

The 1:1 molecular adducts of pyrazine-2,3-dicarboxylic acid with 4-aminobenzoic acid, [(C6H3N2O4)-(C7H8NO2)+], 3-hydroxypyridine, [(C6H4N2O4) (C5H5NO)], and 3-amino-1,2,4-triazole, [(C6H3N2O4)-(C2H5N4)+] have been prepared, and their structures determined by X-ray diffraction methods. All structures involve intra- and inter-molecular hydrogen-bonding interactions. The 1:2 complex of pyrazine-2,3-dicarboxylic acid with triphenylphosphine oxide has also been prepared, and characterized by using spectroscopic methods.

The Crystal and Molecular Structure of the 1:1 Adduct Hydrate of Pyrazine-2,3-dicarboxylic Acid with 1,1-Diethylurea

2000 ◽  
Vol 53 (12) ◽  
pp. 999 ◽  
Author(s):  
Graham Smith ◽  
Colin H. L. Kennard
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Dicarboxylic Acid ◽  
Lattice Water Molecule ◽  
Crystal And Molecular Structure ◽  
Acid Group ◽  
X Ray Diffraction ◽  
Carboxylic Acid Group ◽  
X Ray ◽  
Bonding Interaction

The adduct hydrate of 1,1-diethylurea with pyrazine-2,3-dicarboxylic acid, [(C6H4N2O4)(C5H12N2O)].H2O has been prepared and characterized using low-temperature single-crystal X-ray diffraction methods. A primary asymmetric cyclic hydrogen-bonding interaction, similar to those found in other adducts of 1,1-diethylurea with the nitro-substituted aromatic acids, was found between the amide group of the substituted urea and one carboxylic acid group of the acid. Further peripheral hydrogen-bonding associations involving both the f irst and the second carboxylic acid groups, urea and the lattice water molecule result in a ribbon polymer structure.

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.

Inhibitors of the geotropic response in plants. The crystal structures of 2-[(Naphthalen-2-yl)carbamoyl]benzoic acid (β-Naptalam), 2-(Phenylcarbamoyl)-benzoic acid and 2-(5-Phenyl-1,3,4-oxadiazol-2-yl)benzoic acid

1983 ◽  
Vol 36 (12) ◽  
pp. 2455 ◽  
Author(s):  
G Smith ◽  
CHL Kennard ◽  
GF Katekar
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Benzoic Acid ◽  
Crystal Structures ◽  
Carboxylic Acids ◽  
Intermolecular Hydrogen Bonding ◽  
X Ray Diffraction ◽  
X Ray ◽  
Carboxylic Acid Groups ◽  
Phthalamic Acid

The crystal structures of three geotropically active phthalamic acid derivatives have been determined by means of X-ray diffraction and the structural systematics for the series compared. The three acids are conformationally similar and, in contrast to the tendency among carboxylic acids to form hydrogen-bonded dimers, they exist as monomers with intermolecular hydrogen bonding between the carboxylic acid groups and the nitrogen or oxygen of the amide side chains.

Molecular Cocrystals of Aromatic Carboxylic Acids with 1,1-Diethylurea: Synthesis and the Crystal Structures of a Series of Nitro-Substituted Analogues

2000 ◽  
Vol 53 (3) ◽  
pp. 203 ◽  
Author(s):  
Graham Smith ◽  
Michael G. Coyne ◽  
Jonathan M. White
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acids ◽  
Acid Group ◽  
X Ray Diffraction ◽  
Chain Polymer ◽  
Aromatic Carboxylic Acids ◽  
Nitrobenzoic Acid ◽  
Simple Chain ◽  
A Chain ◽  
Polymeric Structures

Molecular adducts of 1,1-diethylurea with the nitro-substituted aromatic carboxylic acids 2-nitrobenzoic acid, [(C7H5NO4)(C5H12N2O)] (1), 3-nitrobenzoic acid, [(C7H5NO4)(C5H12N2O)] (2), 4-nitrobenzoic acid, [(C7H5NO4)2(C5H12N2O)] (3), 3,5-dinitrobenzoic acid, [(C7H4N2O6)(C5H12N2O)] (4), 5-nitrosalicylic acid, [(C7H5NO5)(C5H12N2O)] (5) and 3,5-dinitrosalicylic acid, [(C7H4N2O7)(C5H12N2O)] (6), have been prepared and characterized by using infrared spectroscopy, and, in the case of four of these [(1), (4), (5) and (6)], by single-crystal X-ray diffraction methods. In all examples, primary cyclic hydrogen-bonding interactions are found between the amide group of the substituted urea and the carboxylic acid group of the acid, while further peripheral associations result predominantly in simple chain polymeric structures, and in one case [adduct (1)], a cyclic tetramer. The crystal structure of the parent 1,1-diethylurea has also been determined, revealing a cyclic hydrogen-bonded tetramer which forms into a chain polymer by weak hydrogen-bonding associations.

Study on a Structure of 2,6-pyridine-dicarboxylic Acid Cobalt Calcium Hexahydrate

2013 ◽  
Vol 739 ◽  
pp. 30-33
Author(s):  
Hai Xing Liu ◽  
Jing Zhong Xiao ◽  
Huan Mei Guo ◽  
Qing Hua Zhang ◽  
Zhang Xue Yu ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Dicarboxylic Acid ◽  
Hydrothermal Reaction ◽  
Crystal Packing ◽  
X Ray Diffraction ◽  
X Ray ◽  
Hydrogen Bonding Interactions ◽  
Pyridinedicarboxylic Acid ◽  
Pyridine Dicarboxylic Acid

The complex C28H32CaCoN4O24has been synthesized from hydrothermal reaction and the crystal structure has been determined by means of single-crystal X-ray diffraction. The Co atom is six-coordinated by two N atoms, four O atoms from two 2,6-pyridinedicarboxylic acid. The Ca atom is eight-coordinated by two N atoms, six O atoms from two 2,6-pyridinedicarboxylic acid and two water molecular. The crystal packing is stabilized by O-H...O hydrogen bonding interactions.

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