Structure of p-hydroxybenzoic acid and p-hydroxybenzoic acid-acetone complex (2/1)

Heath, E. A.; Singh, Pritpal; Ebisuzaki, Y.

doi:10.1107/s0108270192002361

Cited by 45 publications

(53 citation statements)

References 2 publications

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“…The molecular weight was found to be 156.13. The structure of 4-hydroxy benzoic acid hydrate reported here is compared with previous reports for the monohydrate grown from wet acetone solution (Prager et al, 1927;Heath et al, 1992).…”

Section: Resultsmentioning

confidence: 91%

Antibacterial and antifungal activity of Cassia fistula L.: An ethnomedicinal plant

Duraipandiyan¹,

Ignacimuthu²

2007

Journal of Ethnopharmacology

155

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Section: Resultsmentioning

confidence: 91%

Antibacterial and antifungal activity of Cassia fistula L.: An ethnomedicinal plant

Duraipandiyan¹,

Ignacimuthu²

2007

Journal of Ethnopharmacology

155

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“…Since only the structure of p-hydroxybenzoic acid has been investigated (5,6,9), all local and global structural minima on the potential energy hypersurface of the parent antioxidants and their phenoxyl radicals have been fully identified.…”

Section: Resultsmentioning

confidence: 99%

A computational study of the structure‐activity relationships of some p‐hydroxybenzoic acid antioxidants

Vafiadis

Bakalbassis

2003

J Americ Oil Chem Soc

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Equilibrium structures of all derivatized systems of p‐hydroxybenzoic acid, 3,4‐dihydroxybenzoic acid, 3‐methoxy‐4‐hydroxybenzoic acid, and 3,5‐dimethoxy‐4‐hydroxybenzoic acid and calculated structural and energetic molecular descriptors were determined at the B3LYP/6‐31+G(d) density functional theoretical level in an attempt to study their structure‐activity relationships (SAR). The theoretical antioxidant activity trend, derived in terms of hydrogen‐donating capacity against radicals in lipid systems, is in excellent agreement with the experimental one. The lower antioxidant activity of benzoates, experimentally found relative to the homologous cinnamates, could be due to (i) their lower spin delocalization, (ii) their higher calculated heats of formation values in forming radicals (ΔHOF), and (iii) the much stronger electron‐withdrawing effect of the‐COOH group than‐CH=CHCOOH. The low calculated dipole moment values of the global minimum structures of the antioxidants could facilitate their solubilities in nonpolar solvents, hence the ease of hydrogen abstraction. However, highest occupied molecular orbital (HOMO) eigenvalues can neither predict antioxidant activity nor differentiate the same activity between two series of structurally related compounds. Again, density functional theory calculations provide a good molecular descriptor, ΔHOF, to correlate with the antioxidant activity in molecules showing similar structural characteristics.

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“…The dimers in PHBA are held together by hydrogen bonds (2.897 Å) between phenolic groups. The hydrogen-bonded molecules spiral around the twofold screw axes to make up layers of dimmers parallel to (401) [12]. For the PHBA in aqueous solution, hydrogen bonds established between phenolic groups are destroyed and the downshift undergone by the band is due to C-OH stretching.…”

Section: Uv Raman Spectrum Of Phba Aqueous Solutionmentioning

confidence: 98%

“…In crystals, pairs of PHBA molecules are linked through hydrogen bonds (2.635 Å in pure acid) between carboxyl groups to form cyclic dimers [12]. However, in aqueous solution, the hydrogen bonds between carboxyl groups break down.…”

Section: Uv Raman Spectrum Of Phba Aqueous Solutionmentioning

confidence: 99%

Raman spectroscopy of p-hydroxybenzoic acid aqueous solution and surface-unenhanced Raman scattering on silver colloid with ultraviolet excitation

Xu¹,

Fang²

2004

Journal of Colloid and Interface Science

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Structure of p-hydroxybenzoic acid and p-hydroxybenzoic acid-acetone complex (2/1)

Cited by 45 publications

References 2 publications

Antibacterial and antifungal activity of Cassia fistula L.: An ethnomedicinal plant

Antibacterial and antifungal activity of Cassia fistula L.: An ethnomedicinal plant

A computational study of the structure‐activity relationships of some p‐hydroxybenzoic acid antioxidants

Raman spectroscopy of p-hydroxybenzoic acid aqueous solution and surface-unenhanced Raman scattering on silver colloid with ultraviolet excitation

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