Browse
Submit Data
Databases
API
Help

Dataset Information

5 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Intra- and inter-molecular proton transfer in 2,6-diamino-pyridinium 4-hy-droxy-pyridin-1-ium-2,6-dicarboxyl-ate.

ABSTRACT: Chelidamic acid (4-hy-droxy-pyridine-2,6-dicarb-oxy-lic acid) and 2,6-diamino-pyridine react to form the title salt, C(5)H(8)N(3) (+)·C(7)H(4)NO(5) (-); there are two formula units in the asymmetric unit. The pyridine N atom of 2,6-diamino-pyridine is protonated whereas chelidamic acid is deprotonated at both carboxyl-ate groups but protonated at the N atom; the reaction involves intra- and inter-molecular proton transfer. In the crystal, each 2,6-diamino-pyridinium cation participates in five strong N-H?O hydrogen bonds (including one bifurcated hydrogen bond). The crystal structure also features strong O-H?O hydrogen bonds between the chelidamate anions, leading to chains along the a axis.

SUBMITTER: Ton QC

PROVIDER: S-EPMC3470218 | biostudies-other | 2012 Oct

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

Intra- and inter-molecular proton transfer in 2,6-diamino-pyridinium 4-hy-droxy-pyridin-1-ium-2,6-dicarboxyl-ate.

Ton Quoc-Cuong QC Bolte Michael M

Acta crystallographica. Section E, Structure reports online 20120905 Pt 10

Chelidamic acid (4-hy-droxy-pyridine-2,6-dicarb-oxy-lic acid) and 2,6-diamino-pyridine react to form the title salt, C(5)H(8)N(3) (+)·C(7)H(4)NO(5) (-); there are two formula units in the asymmetric unit. The pyridine N atom of 2,6-diamino-pyridine is protonated whereas chelidamic acid is deprotonated at both carboxyl-ate groups but protonated at the N atom; the reaction involves intra- and inter-molecular proton transfer. In the crystal, each 2,6-diamino-pyridinium cation participates in five s ...[more]

PMID: 23125662

Similar Datasets

2-Amino-pyrimidinium 4-hy-droxy-pyridinium-2,6-dicarboxyl-ate monohydrate.

Project description:In the crystal structure of the title compound, C(4)H(6)N(3) (+)·C(7)H(4)NO(5) (-)·H(2)O, inter-molecular N-H?N, N-H?O and O-H?O hydrogen bonds link the cations and anions into almost planar sheets parallel to (102). These hydrogen-bonded sheets are packed into the crystal with the formation of centrosymmetric voids of 68?Å(3), which are filled by the water mol-ecules, each of which is disordered over four positions.

| S-EPMC3008026 | biostudies-literature

Bis(2,6-diamino-pyridinium) bis-(pyridine-2,6-dicarboxyl-ato)zincate(II) monohydrate.

Project description:In the title hydrated mol-ecular salt, (C(5)H(8)N(3))(2)[Zn(C(7)H(3)NO(4))(2)]·H(2)O, the Zn(II) atom is coordinated by two O,N,O'-tridentate pyridine-2,6-dicarboxyl-ate dianions, generating a slightly distorted trans-ZnN(2)O(4) octa-hedral coordination geometry for the metal ion. In the crystal, a network of O-H?O, N-H?O and C-H?O hydrogen bonds involving the cations, anions and water mol-ecules results in a three-dimensional network.

| S-EPMC3120536 | biostudies-literature

Hexaaqua-magnesium(II) bis-(pyridinium-2,6-dicarboxyl-ate).

Project description:In the title compound, [Mg(H(2)O)(6)](C(7)H(4)NO(4))(2), a single six-coordinate Mg(2+) cation (site symmetry 2/m) is bonded to six water mol-ecules in a distorted octa-hedral geometry. The crystal packing between the complex cation and the zwitterionic organic cation (m symmetry) is stabilized by inter-molecular O-H?O hydrogen bonds and weak inter-molecular C-H?O inter-actions.

| S-EPMC3011450 | biostudies-literature

Tetra-kis(2,6-diamino-pyridinium) diphthalate 2,6-diamino-pyridine.

Project description:In the title compound, 4C(5)H(8)N(3) (+)·2C(8)H(4)O(4) (2-)·C(5)H(7)N(3), the asymmetric unit consists of two protonated diamino-pyridine cations, one phthalate anion and one half of a diamino-pyridine mol-ecule, which has twofold rotation symmetry and is disordered over two positions with a site-occupancy ratio of 0.534?(3):0.466?(3). In the disordered structure, both pyridine rings are essentially planar, with maximum deviations of 0.011?(2) and 0.006?(2)?Å, and these two rings are inclined to one another at a dihedral angle of 79.86?(10)°. In the crystal structure, inter-molecular N-H?O and C-H?O hydrogen bonds link the ions and mol-ecules into a three-dimensional network. The structure is further stabilized by C-H?? inter-actions.

| S-EPMC2971263 | biostudies-literature

Bis(2,6-diamino-pyridin-1-ium) hexa-aqua-cobalt(II) disulfate dihydrate.

Project description:In the title compound, (C(5)H(8)N(3))(2)[Co(H(2)O)(6)](SO(4))(2)·2H(2)O, the complete complex cation is generated by crystallographic inversion symmetry, such that the Co(II) cation is octa-hedrally coordinated by six water mol-ecules. The organic cation is essentially planar, with a maximum deviation of 0.013?(1)?Å. In the crystal structure, the ions and mol-ecules are linked into a pseudo-layered three-dimensional supra-molecular network via O-H?O and N-H?O hydrogen bonds. Weak inter-molecular ?-? inter-actions further stabilize the crystal structure [centroid-centroid distance = 3.5231?(4)?Å].

| S-EPMC3007492 | biostudies-literature

2,6-Diamino-pyridinium bis-(4-hydroxy-pyridine-2,6-dicarboxyl-ato-?O,N,O)ferrate(III) dihydrate.

Project description:The reaction of iron(II) sulfate hepta-hydrate with the proton-transfer compound (pydaH)(hypydcH) (pyda = pyridine-2,6-diamine; hypydcH(2) = 4-hydroxy-pyridine-2,6-dicarboxylic acid) in an aqueous solution led to the formation of the title compound, (C(5)H(8)N(3))[Fe(C(7)H(3)NO(5))(2)]·2H(2)O. The anion is a six-coordinated complex with a distorted octa-hedral geometry around the Fe(III) atom. Extensive inter-molecular O-H?O, N-H?O and C-H?O hydrogen bonds, involving the complex anion, (pydaH)(+) counter-ion and two uncoordinated water mol-ecules, and ?-? [centroid-to-centroid distance 3.323?(11)?Å] and C-O?? [O-centroid distance 3.150?(15)?Å] inter-actions connect the various components into a supra-molecular structure.

| S-EPMC2959321 | biostudies-literature

2,6-Diamino-pyridinium bis-(4-hydroxy-pyridine-2,6-dicarboxyl-ato-?O,N,O)chromate(III) dihydrate.

Project description:The reaction of chromium(III) nitrate hexa-hydrate, pyridine-2,6-diamine and 4-hydroxy-pyridine-2,6-dicarboxylic acid in a 1:2:2 molar ratio in aqueous solution resulted in the formation of the title compound, (C(5)H(8)N(3))[Cr(C(7)H(3)NO(5))(2)]·2H(2)O or (pydaH)[Cr(hypydc)(2)]·2H(2)O (where pyda is pyridine-2,6-diamine and hypydcH(2) is 4-hydroxy-pyridine-2,6-dicarboxylic acid). Each Cr(III )atom is hexa-coordinated by four O and two N atoms from two (hypydc)(2-) fragments, which act as tridentate ligands, in a distorted octa-hedral geometry. The O-Cr-O-C torsion angles between the two planes of the (hypydc)(2-) fragments [-99.81?(17) and 97.77?(17)°] indicate that these two units are almost perpendicular to one another. In the crystal structure, extensive O-H?O, N-H?O and C-H?O hydrogen bonds with D?A distances ranging from 2.560?(2) to 3.279?(3)?Å, ion pairing, C-O?? [O?? = 3.166?(2)?Å] and ?-? stacking inter-actions between (hypydc)(2-) and (pydaH)(+) rings [with a centroid-centroid distance of 3.3353?(14)?Å] contribute to the formation of a three-dimensional supra-molecular structure.

| S-EPMC2960621 | biostudies-literature

2,6-Diamino-pyridinium dihydrogen phosphate.

Project description:In the crystal structure of the title compound, C(5)H(8)N(3) (+)·H(2)PO(4) (-), N-H?O hydrogen bonds, involving the unprotonated amino-group and the NH(+) group in the pyridinium ring and dihydrogenphosphate O atoms, link the cations and anions. A long chain-like stacking of dihydrogenphosphate anions along the c-axis direction is constructed by O-H?O hydrogen bonds. Also along the c-axis direction, ?-? stacking between inversion-related pyridinium rings [centroid-centroid distance = 3.8051?(10)?Å] forms columnar stacks of cations.

| S-EPMC3435763 | biostudies-literature

2,6-Diamino-pyridinium 2-carb-oxy-benzoate.

Project description:In the crystal of the title mol-ecular salt, C(5)H(8)N(3) (+)·C(8)H(5)O(4) (-), the diamino-pyridine cation and the phthalate anion are linked by a pair of N-H⋯O hydrogen bonds. Within the phthalate anion, an almost symmetrical O-H⋯O hydrogen bond is observed. The ion pairs are linked by further N-H⋯O hydrogen bonds, generating a two-dimensional network lying parallel to (10).

| S-EPMC3008098 | biostudies-literature

2,3-Diamino-pyridinium 2-hy-droxy-benzoate.

Project description:In the title mol-ecular salt, C(5)H(8)N(3) (+)·C(7)H(5)O(3) (-), the 2,3-diamino-pyridinium cation is essentially planar, with a maximum deviation of 0.006?(2)?Å. In the crystal, adjacent cations and anions are linked by pairs of N-H?O hydrogen bonds, generating R(2) (2)(8) loops. These dimers are linked by further N-H?O hydrogen bonds and C-H?O inter-actions to form sheets lying parallel to (001). A typical intra-molecular O-H?O hydrogen bond is also observed in the salicylate (2-hy-droxy-benzoate) anion, which generates an S(6) ring. The crystal structure also features ?-? stacking inter-actions between the pyridinium rings of the cations, with a centroid-centroid distance of 3.5896?(15)?Å.

| S-EPMC3247505 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data