Bifurcated hydrogen-bonded synthons in molecular complexes of picolines with chloranilic acid

doi:10.1039/B912539F

Paper

Bifurcated hydrogen-bonded synthons in molecular complexes of picolines with chloranilic acid

Published Feb 23, 2010 · Martin Adam, A. Parkin, L. Thomas

CrystEngComm

Q2 SJR score

18

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

Chloranilic acid (2,5-dichloro-3,6-dihydroxybenzoquinone, CA) readily forms molecular complexes with the three methylpyridine (picoline) isomers in both 1 : 1 and 1 : 2 ratios. In each case a predictable hydrogen-bonded supramolecular unit is formed consisting of a P:C:C:P or a P:C:P arrangement for each of the stoichiometric ratios, respectively. At least one proton is transferred from a chloranilic acid molecule to the nitrogen of the picoline in all the structures. The molecules are held together by a series of bifurcated hydrogen bonds in which a large degree of variation in the directionality can be observed. The proton depleted chloranilate ions show a delocalisation of charge across the entire molecule in the presence of highly bifurcated hydrogen bonds. The variation of the supramolecular units is discussed with particular reference to the degree of bifurcation in the hydrogen bonds.

Study Snapshot

Chloranilic acid forms molecular complexes with picolines, forming predictable supramolecular units with variable directionality and a delocalization of charge across the entire molecule.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Bifurcated hydrogen-bonded synthons in molecular complexes of picolines with chloranilic acid

Sign up to use Study Snapshot

References

Hydrogen-bonded structures of the isomeric 2-, 3- and 4-carbamoylpyridinium hydrogen chloranilates.

The isomeric 2-, 3-, and 4-carbamoylpyridinium hydrogen chloranilates show acid-base interactions involving H-atom transfer, with pyridinium N-H...(O,O) bifurcated hydrogen bonds acting as primary intermolecular interactions.

Hydrogen bonding in 1,2-diazine-chloranilic acid (2 : 1) studied by a 14N nuclear quadrupole coupling tensor and multi-temperature X-ray diffraction.

The hydrogen bonding in 1,2-diazine-chloranilic acid (2:1) involves jumping motion in the double-minimum potential, with the electron distribution of the extreme electronic states changing with temperature.

Hydrogen transfer in pentachlorophenol – dimethylpyridine complexes

Hydrogen transfer in pentachlorophenol-dimethylpyridine complexes depends on the pKa value and the presence of weak C-H-O hydrogen bonds, with weak C-H-O bonds influencing this process.

Bis(3-picolinium) chloranilate dihydrate

Bis(3-picolinium) chloranilate dihydrate has a unique structure with a centrally symmetric chloranilate-3-picolinium 1:2 unit and a complex water-molecular network.

Imaging proton migration from X-rays and neutrons

Proton migration in the urea-phosphoric acid system can be clearly observed using X-ray difference Fourier maps, with a greater apparent shift observed from X-ray diffraction than from neutron diffraction.

Citations

Quantitative analysis of intermolecular interactions in cocrystals and a pair of polymorphous cocrystal hydrates from 1,4-dihydroquinoxaline-2,3-dione and 1H-benzo[d]imidazol-2(3H)-one with 2,5-dihydroxy-1,4-benzoquinones: a combined X-ray structural and theoretical analysis

Cocrystals and cocrystal hydrates from 1,4-dihydroquinoxaline-2,3-dione and 1H-benzo[d]imidazol-2(3H)-one with 2,5-dihydroxy-1,4-benzoquinones show strong hydrogen

Crystal structural analysis of methyl-substituted pyrazines with anilic acids: a combined diffraction, inelastic neutron scattering, 1 H-NMR study and theoretical approach

Methyl-substituted pyrazines with anilic acids show good agreement in crystal structures and bonding properties, with methyl group tunneling being a potential mechanism for tunneling.

Synthesis, structural characterization, spectroscopic, thermal, dielectric and Hirshfeld surface analysis of 1-(2-methoxyphenyl)piperazinium chloranilate

The new compound 1-(2-methoxyphenyl)piperazinium chloranilate (MPP.CA) shows promising properties for electronic applications, with a hopping conduction mechanism and transition phase observed in dielectric constant measurements.

Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hydroxypyridine and 4-hyroxypyridine

The hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hydroxypyridine, and 4-hyroxypyridine show short O-HO and N-HO hydrogen bonds.

Structure–Spectra Correlations in Anilate Complexes with Picolines

Structure-spectroscopy correlations in anilate complexes with picolines can aid in designing and recognizing supramolecular architectures.