Structure of the sodium salt of 1,4,5,8-naphthalenetetracarboxylic acid 4,5-anhydride hydrate

Fitzgerald, L. J.; Gallucci, Judith; Gerkin, R. E.

doi:10.1107/s0108270191010983

Cited by 6 publications

(3 citation statements)

References 4 publications

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“…The geometric parameters of this compound are in general agreement with analogous parameters for naphthalic anhydrides reported previously (Blackburn et al, 1997;Fitzgerald et al, 1991Fitzgerald et al, , 1992.…”

Section: Commentsupporting

confidence: 88%

Naphthalene-1,4,5,8-tetracarboxylic 1,8-anhydride

Yuan

Zhou

et al. 2005

Acta Cryst E

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Section: Commentsupporting

confidence: 88%

Naphthalene-1,4,5,8-tetracarboxylic 1,8-anhydride

Yuan

Zhou

et al. 2005

Acta Cryst E

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“…For the structures of naphthalene-1,4,5,8-tetracarboxylic acid 1,8-anhydride, its DMSO solvate and several metal complexes, see: Blackburn et al (1997); Fitzgerald et al (1992); Robl (1987); Xu et al (2005a,b. ) For hydrogen bonds, see: Desiraju & Steiner (1999).…”

Section: Related Literaturementioning

confidence: 99%

Naphthalene-1,4,5,8-tetracarboxylic acid 1,8-anhydride–4,4′-bipyridine (1/1)

et al. 2009

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The title compound, C14H6O7·C10H8N2, has been hydrothermally synthesized. Structural ananlysis indicates that the crystals are produced by cocrystallization of naphthalene-1,4,5,8-tetracarboxylic acid 1,8-anhydride and 4,4′-bipyridine (bpy) molecules. The crystal packing is stabilized by intermolecular O—H⋯N and C—H⋯O hydrogen bonds and π–π stacking interactions [centroid–centroid distances = 3.5846 (9) Å].

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“…The fit of eqn (14) to the kinetic data in Fig. 4B was obtained using k −1 = 0.000275, k 1 = 0.00165 and K II-2 = 4 × 10 −4 (pK II-2 = 3.4), K I-H4 = K I-H2 = 3 × 10 −4 (pK I-H4 = pK I-H3 = 3.52).…”

Section: Quantitative Analysis Of Kineticsmentioning

confidence: 99%

Mechanism of 1,4,5,8-naphthalene tetracarboxylic acid dianhydride hydrolysis and formation in aqueous solution

et al. 2006

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The study of highly conjugated, carbonyl-containing molecules such as 1,4,5,8-naphthalene tetracarboxylic dianhydride, III, is of interest since reactivity differences and transmission of electronic effects through the conjugated framework can be evidenced. The kinetics of hydrolysis of III in aqueous solution were determined from 5 M acid to pH 10. In basic solution hydrolysis of III yields, sequentially, 1,4,5,8-naphthalene diacid monoanhydride, II, and 1,4,5,8-naphthalene tetracarboxylic acid, I. The second order rate constant for alkaline hydrolysis is 200 fold higher for the first ring opening. The water-catalyzed hydrolysis of III yields a pH-dependent mixture of ionic forms of I and II. The rate constant for water-catalyzed hydrolysis of III is 25 fold higher than that for II. In concentrated acid the rates for reaching equilibrium (I, II and III) increase and III is the major product. The pK(a)s of I (3.24, 5.13 and 6.25) and II (3.05, 5.90) were determined by potentiometric, fluorescence and UV spectroscopy titrations and by quantitative fit of the kinetic and equilibrium data. The apparent, pH-dependent, equilibrium constants, K(EqII), for anhydride formation between I and II were obtained from the UV spectra. The quantitative fit of kinetic and equilibrium data are consistent with the assumption that anhydride formation only proceeds with the fully protonated species for both I and II and permitted the estimation of the equilibrium constants for anhydride formation, K(EqII). The value of K(EqII) (I <==> II) between pH 1 and 6 was ca. 5. Geometry optimization calculations in the gas phase of the reactions of III in alkaline, neutral and acid conditions, at the DFT level of theory, gave electronic distributions that were qualitatively consistent with the experimental results.

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Structure of the sodium salt of 1,4,5,8-naphthalenetetracarboxylic acid 4,5-anhydride hydrate

Cited by 6 publications

References 4 publications

Naphthalene-1,4,5,8-tetracarboxylic 1,8-anhydride

Naphthalene-1,4,5,8-tetracarboxylic 1,8-anhydride

Naphthalene-1,4,5,8-tetracarboxylic acid 1,8-anhydride–4,4′-bipyridine (1/1)

Mechanism of 1,4,5,8-naphthalene tetracarboxylic acid dianhydride hydrolysis and formation in aqueous solution

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