Hydrogen-bonding network in the organic salts of 4-nitrobenzoic acid

Chumakov, Yurii; Simonov, Yurii A.; Grozav, Mata; Crişan, Manuela; Bocelli, Gabriele; Yakovenko, Andrey A.; Lyubetsky, Dmitry

doi:10.2478/s11532-006-0023-3

Cited by 14 publications

(29 citation statements)

References 10 publications

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“…It is evident that in all these compounds an N-atom of the DEA molecule is protonated and counter ions are anions of acids except of the two phenols (QECHOX, NINZAN) and one base (OHUWIZ). The only relevant CSD entry is the compound with refcode LIXBAG which is salt between DEA and p-nitrobenzoic acid [20]. The same supramolecular association of the cationic and anionic components into dimers found in our title compounds is observed in this compound.…”

Section: Csd Surveysupporting

confidence: 58%

“…In both salts cations are associated with anions into dimers by the same Hbonding which closes cycles with the graph-set notations of R2 2 (9). The analogical 1:1 association mode is found in salts of DEA with p-nitrobenzoic [20] and o-nitrobenzoic acid [21]. Thus, H-bonding which generates these dimers may be considered as a synthon responsible for yielding of salts between DEA and mono-substituted benzoic acids.…”

Section: Resultsmentioning

confidence: 92%

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X-ray structures of organic salts between diethanolamine and ortho- and para-isomers of aminobenzoic acid: A specific synthon responsible for an association of the components

et al. 2018

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Two organic salts between diethanolamine (DEA) and ortho- and para-isomers (OABA and PABA) of aminobenzoic acid (ABA) have been obtained and their X-ray single crystal structures determined. In both salts, cationic and anionic components are incorporated into dimers by the two H-bonds formed between ABA carboxylate oxygen atoms and nitrogen and one of oxygen atoms of DEA which close a cycle with the graph-set notation of R22(9). Further dimers are associated by intricate systems of the H-bonds into 1D- and 3D-network structures in crystals of DEA·OABA and DEA·PABA, respectively. H-bonding which generates these dimers may be considered as a synthon specific for yielding of salts between DEA and mono-substituted aromatic benzoic acids.

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Section: Csd Surveysupporting

confidence: 58%

Section: Resultsmentioning

confidence: 92%

X-ray structures of organic salts between diethanolamine and ortho- and para-isomers of aminobenzoic acid: A specific synthon responsible for an association of the components

et al. 2018

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“…As mentioned above, there are literature precedents for the cation in 3 and an analysis of these reveals significant conformational flexibility in their molecular structures. Indeed, there are 10 other cations in structures that have three-dimensional coordinates and that do not suffer from disorder [38][39][40][41][42][43][44][45]. Key torsion angle data for these are collected in Table 2.…”

Section: Molecular Structures Of the Cations In 1-3mentioning

confidence: 99%

Three ammonium salts of sulfathiazole: crystallography and anti-microbial assay

Aznan

Abdullah

Khoo

et al. 2015

Zeitschrift Für Kristallographie - Crystalline Materials

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The crystal and molecular structures of three ammonium salts derived from sulfathiazole are described. In each case, the anion is in the azanide form, features an intramolecular S←O interaction, and adopts a U-shape. The structures of two cations, [R(HOCH 2 CH 2 )NH 2 ] + , namely for R = Me (1) and iPr (2), are unprecedented in the crystallographic literature. Extensive hydrogen bonding is observed in all crystal structures and leads to a two-dimensional array for 1, and three-dimensional architectures for each of 2 and 3 (R = CH 2 CH 2 OH). The salts exhibited anti-microbial activity against a range of Gram-positive and Gram-negative bacteria, and proved bactericidal toward Vibrio parahaemolyticus, but had no advantage over sulfathiazole itself.

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“…The crystal structures of only eight anhydrous morpholinium salts of the substituted benzoic acid analogues have been reported, e.g. with 4-nitrobenzoic acid (Chumakov et al, 2006), 5-nitrosalicylic acid (Smith et al, 2005), 4-aminosalicylic acid (André et al, 2009) and a series of isomeric chloronitrobenzoates (i.e. 2,4-, 2,5-, 4,2-, 4,3-and 5,2-chloronitro;Ishida et al, 2001a,b,c).…”

Section: Introductionmentioning

confidence: 99%

Cyclic heterotetrameric and low-dimensional hydrogen-bonded polymeric structures in the morpholinium salts of ring-substituted benzoic acid analogues

Smith

Lynch²

2016

Acta Crystallogr C

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The morpholinium (tetrahydro-2H-1,4-oxazin-4-ium) cation has been used as a counter-ion in both inorganic and organic salt formation and particularly in metal complex stabilization. To examine the influence of interactive substituent groups in the aromatic rings of benzoic acids upon secondary structure generation, the anhydrous salts of morpholine with salicylic acid, C4H10NO(+)·C7H5O3(-), (I), 3,5-dinitrosalicylic acid, C4H10NO(+)·C7H3N2O7(-), (II), 3,5-dinitrobenzoic acid, C4H10NO(+)·C7H3N2O6(-), (III), and 4-nitroanthranilic acid, C4H10NO(+)·C7H5N2O4(-), (IV), have been prepared and their hydrogen-bonded crystal structures are described. In the crystal structures of (I), (III) and (IV), the cations and anions are linked by moderately strong N-H...Ocarboxyl hydrogen bonds, but the secondary structure propagation differs among the three, viz. one-dimensional chains extending along [010] in (I), a discrete cyclic heterotetramer in (III), and in (IV), a heterotetramer with amine N-H...O hydrogen-bond extensions along b, giving a two-layered ribbon structure. With the heterotetramers in both (III) and (IV), the ion pairs are linked though inversion-related N-H...Ocarboxylate hydrogen bonds, giving cyclic R4(4)(12) motifs. With (II), in which the anion is a phenolate rather than a carboxylate, the stronger assocation is through a symmetric lateral three-centre cyclic R1(2)(6) N-H...(O,O') hydrogen-bonding linkage involving the phenolate and nitro O-atom acceptors of the anion, with extension through a weaker O-H...Ocarboxyl hydrogen bond. This results in a one-dimensional chain structure extending along [100]. In the structures of two of the salts [i.e. (II) and (IV)], there are also π-π ring interactions, with ring-centroid separations of 3.5516 (9) and 3.7700 (9) Å in (II), and 3.7340 (9) Å in (IV).

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Hydrogen-bonding network in the organic salts of 4-nitrobenzoic acid

Abstract: Abstract:The crystal structures of six novel salts of 4-nitrobenzoic acid -namely, 2-hydroxyethylammonium 4-nitrobenzoate

Cited by 14 publications

References 10 publications

X-ray structures of organic salts between diethanolamine and ortho- and para-isomers of aminobenzoic acid: A specific synthon responsible for an association of the components

X-ray structures of organic salts between diethanolamine and ortho- and para-isomers of aminobenzoic acid: A specific synthon responsible for an association of the components

Three ammonium salts of sulfathiazole: crystallography and anti-microbial assay

Cyclic heterotetrameric and low-dimensional hydrogen-bonded polymeric structures in the morpholinium salts of ring-substituted benzoic acid analogues

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