The crystal structure of isophthalic acid

Derissen, J. L.

doi:10.1107/s056774087400803x

Cited by 64 publications

(34 citation statements)

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“…33¡ with respect to the benzene ring due to steric hindrance. 15 For the picolinate ion, some steric hindrance is expected between the CO 2ã nd the non-bonding electron pair of the pyridine ring nitrogen atom because they are both negatively charged and in adjacent positions. Therefore, rotation of the carboxylate group from the pyridine ring is distinctly possible.…”

Section: Resultsmentioning

confidence: 99%

Three distinct geometries of surface‐adsorbed carboxylate groups

Suh

Kim

1998

J Raman Spectroscopy

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Section: Resultsmentioning

confidence: 99%

Three distinct geometries of surface‐adsorbed carboxylate groups

Suh

Kim

1998

J Raman Spectroscopy

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“…The R 2 2 (8) dimers formed by two acid groups of each trimesic acid molecule produce an infinite zigzag ribbon along the b axis (Figure 2A), a motif similar to that found in the structure of isophthalic acid. [17] The third carboxylic acid groups link the ribbons together through 12-membered hydrogen-bonded rings that contain two ethanol molecules. The resulting expanded holes are large enough to contain a pyrene molecule and the ethyl groups of two ethanol molecules from an adjacent layer.…”

Section: Resultsmentioning

confidence: 99%

Self-Assembly of 1,3,5-Benzenetricarboxylic (Trimesic) Acid and Its Analogues

Kolotuchin¹,

Thiessen²,

Fenlon³

et al. 1999

Chem. Eur. J.

117

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A crystalline inclusion complex between 1,3,5-benzenetricarboxylic acid (trimesic acid, 1) and pyrene was grown from diethyl ether/ethanol and its structure was determined by X-ray analysis. Trialkyltrimesic acids 4 b ± 4 e were synthesized in seven steps from 1,3,5-trichlorobenzene (5). Trimethyltrimesic acid (4 a) was synthesized in four steps from mesitylene. All five substituted trimesic acids were crystallized to determine their potential as clathrate hosts and to compare their solidstate structures with the parent trimesic acid. The X-ray structures of 4 a ± 4 d were resolved and are reported. A covalent analogue of a trimesic acid dimer (13) was synthesized in seven steps from 2-butylisophthalic acid and its solid-state structure determined.

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“…Two protons internal (H k ) to the salt bridge establish a primary interaction with two lone pairs of a carboxylate; the resulting zigzag tapes are like those of isophthalic acid, [25] where carboxylic acid dimers form the two-point intermolecular hydrogen bonds. Two protons internal (H k ) to the salt bridge establish a primary interaction with two lone pairs of a carboxylate; the resulting zigzag tapes are like those of isophthalic acid, [25] where carboxylic acid dimers form the two-point intermolecular hydrogen bonds.…”

Section: Resultsmentioning

confidence: 99%

From Molecules to the Crystalline Solid: Secondary Hydrogen-Bonding Interactions of Salt Bridges and Their Role in Magnetic Exchange

et al. 1999

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The primary two-point hydrogen-bond contact of p-substituted benzamidinium cations to benzoate anions in [D 6 ]DMSO forms a salt bridge as described by a classical Hammett relation. At carboxylate: amidinium proportions greater than 1:1, amidinium hydrogen atoms external to the salt bridge associate to carboxylate. This complementary interaction of four protons and four lone pairs of the amidinium ± carboxylate salt bridge creates closure of the hydrogen-bonding network in 3-amidinium benzoate. Structural characterization of this solid shows that the primary amidinium ± carboxylate interaction of the salt bridge, which leads to zigzag tapes, is augmented by lateral hydrogen bonding, forming ladder structures of oppositely oriented salt bridges. The ladders crosslink tapes, thus setting the three-dimensional structure of the system. We have exploited this secondary hydrogen-bonding interaction to construct layered magnetic solids based on the salt bridge formed between 3-cyanobenzamidinium and 2,2,4,4-tetramethylpyrroline-N-oxyl-3-carboxylate. In this solid, the nitroxyl radical moiety participates in the hydrogen-bonding network, truncating salt bridge ladder formation by capping (salt bridge) 2 ladder segments. These segments are linked to each other via the secondary hydrogen-bonding interaction of the salt bridge to form isolated linear chains of nitroxyl radicals running diagonally within the layer. Magnetic susceptibility studies show that the nitroxyl spin can propagate through the secondary hydrogen bond. When a water molecule in the solid formed from benzamidinium and 2,2,5,5-tetramethyl-3-carboxypyrroline-1-oxyl interrupts the pathway, magnetic coupling of the spins is obstructed. These results show that the hydrogen bonds external to salt bridges can both set structure and mediate magnetic organization, establishing the salt bridge as a useful synthon in the design of layered magnetic materials.Keywords: crystal engineering´hydrogen bonds´layered compoundś magnetic properties´supramolecular salt-bridges [a] Prof.

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The crystal structure of isophthalic acid

Abstract: Abstract. Benzene-1,3-dicarboxylic acid, C6Ha(COOH)2

Cited by 64 publications

References 1 publication

Three distinct geometries of surface‐adsorbed carboxylate groups

Three distinct geometries of surface‐adsorbed carboxylate groups

Self-Assembly of 1,3,5-Benzenetricarboxylic (Trimesic) Acid and Its Analogues

From Molecules to the Crystalline Solid: Secondary Hydrogen-Bonding Interactions of Salt Bridges and Their Role in Magnetic Exchange

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