A structural study of seven salt forms of sulfonated azo dyes containing nitrile functional groups

Astbury, Catherine; Conway, Linda K.; Gillespie, Cheska; Hodge, K.; Innes, Elaine; Kennedy, Alan R.

doi:10.1016/j.dyepig.2012.11.025

Cited by 11 publications

(11 citation statements)

References 27 publications

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“…In earlier studies, a wide variety of salt forms of monosulfonated azo dyes were formed [5][6][7]. During this work, two structures containing di-deprotonated azo ions were unexpectedly obtained, [Ba(17*)(OH 2 ) 5 ] and [K 3 (3)(3*)(OH 2 )], Figures 8 and 9.…”

Section: Structures Of Forms Containing Dianionsmentioning

confidence: 73%

“…The crystal structures of s-block metal salt forms of monosulfonated azo dyes have been discussed previously [5][6][7]. It was shown that their coordination behaviour and gross structural features are largely dependent of the position of the sulfonate group and the identity of the metal ion.…”

Section: Structures Of Na Salt Formsmentioning

confidence: 99%

“…The ability to quickly form many closely related molecules, that are all variations on a theme, also makes azo compounds a good choice for systematic structural studies. Relatively large-scale solid-state structural studies on salt forms of monosulfonated azo dyes have been published [5][6][7], as has work on salt forms of disulfonated azo dyes [8][9][10]. Crystallographic work on salt forms of sulfonated azo pigments is also available.…”

Section: Introductionmentioning

confidence: 99%

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Monosulfonated Azo Dyes: A Crystallographic Study of the Molecular Structures of the Free Acid, Anionic and Dianionic Forms

et al. 2020

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Crystallographic studies of monosulfonated azo dyes have concentrated on the salt forms that contain the azo anion. Here we present a study that compares the structures of these anions with protonated free acid forms and with doubly deprotonated dianion forms. To this end, the new single crystal diffraction structures of 13 systematically related free acid forms of monosulfonated azo dyes are presented, together with three new structures of doubly deprotonated forms and two new structures of Na salt forms of azo anions. No structures of dideprotonated monosulfonated azo dyes have previously been reported and this paper also reports the first crystal structure of an azo dye with a hydronium cation. The geometries of the free acid, anion and dianion forms are compared to literature equivalents. It is shown that protonation of the azo bond gives predictable bond lengthening and shortening, which is of a greater magnitude than similar effects caused by azo-hydrazone tautomerisation, or the smaller again effects caused by the resonance electron donation from O or N based substituents. The dianion containing structures have twisted dianion geometries that can be understood based on the resonance effects of the phenoxide groups and upon the needs to bond to a relatively high number of metal cations.

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Section: Structures Of Forms Containing Dianionsmentioning

confidence: 73%

Section: Structures Of Na Salt Formsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Monosulfonated Azo Dyes: A Crystallographic Study of the Molecular Structures of the Free Acid, Anionic and Dianionic Forms

et al. 2020

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“…Molecular representations of BEMDAZ,49 CIKCUV, 50,51 FEZHOJ,52 XARZIA,53 and RIHCIW 54 (acronyms used in the CSD).…”

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confidence: 99%

Adding Only One Priority Rule Allows Extending CIP Rules to Supramolecular Systems

Alkorta

Elguero

Cintas³

2015

Chirality

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There are frequent situations both in supramolecular chemistry and in crystallography that result in stereogenic centers, whose absolute configuration needs to be specified. With this aim we propose the inclusion of one simple additional rule to the Cahn‐Ingold‐Prelog (CIP) system of priority rules stating that noncovalent interactions have a fictitious number between 0 and 1. Chirality 27:339–343, 2015. © 2015 Wiley Periodicals, Inc.

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“…Structural analyses of the metal complexes, which consist of alternating inorganic/organic layers, revealed that pyrazole-4-sulfonate is an extremely versatile ligand, due to the coordination flexibility of the sulfonate group and the ability of the pyrazole moiety to participate in H-bonding, aromatic interactions, and coordination with metals. Aryl sulfonate ligands have been found to be useful for the construction of various layered solids and metal–organic frameworks − and continue to receive attention due to various applications such as CO 2 capture and conversion, , luminescent materials, , and dyes. − …”

Section: Introductionmentioning

confidence: 99%

Layered Inorganic–Organic 3,5-Dimethylpyrazole-4-Sulfonate Films for Protection of Copper Surfaces against Corrosion

Isawi

Jianrattanasawat

Tripodianos

et al. 2021

Crystal Growth & Design

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A series of 11 compounds, including alkali (Li, Na, K, Rb, Cs) and alkaline-earth (Mg, Ca, Sr, Ba) coordination polymers, transition-metal (Cu, Cd) complexes, and the ammonium salt of 3,5-dimethylpyrazole-4-sulfonic acid (HL), were synthesized. Single crystals of HL, and CdL 2 (H 2 O) 3 •2H 2 O were obtained from aqueous solutions either by evaporation or acetone vapor diffusion. Characterization by single-crystal X-ray diffraction reveals that the coordination compounds of L − (except Cu) possess alternating inorganic−organic layered structures, in which L − engages in extensive charge-assisted networks of H-bonding and aromatic interactions as well as metal coordination through the pyrazole N atom and/or the sulfonate O atom. A topological analysis and classification of underlying metal−organic or hydrogen-bonded networks uncover a number of distinct topological nets (3,5L2, hcb, 6,6L1, 3,5C1, 3,8L28, hex, and pcu). A thermogravimetric analysis shows that HL and NH 4 L are stable up to 285 and 90 °C, respectively, whereas the anhydrous metal compounds decompose above 200−230 °C. The pK a values of 3,5-dimethylpyrazole-4-sulfonic acid (HL) and pyrazole-4-sulfonic acid were determined by 1 H NMR titrations with H 2 SO 4 . Copper corrosion experiments indicate that 3,5-dimethylpyrazole-4sulfonic acid (HL) is a better anticorrosion agent than the parent pyrazole-4-sulfonic acid at pH 4, whereas the coordination polymers of L − offer weaker corrosion protection in comparison to the corresponding pyrazole-4-sulfonate complexes. The latter result is corroborated by the less compact and less robust thin films formed by metal−L compounds, as indicated by scanning electron microscopy/energy dispersive X-ray spectroscopy (SEM/EDS) measurements, and the weaker acidity of HL, which allows for easier protonation of the conjugate base L − in metal−L compounds.

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A structural study of seven salt forms of sulfonated azo dyes containing nitrile functional groups

Cited by 11 publications

References 27 publications

Monosulfonated Azo Dyes: A Crystallographic Study of the Molecular Structures of the Free Acid, Anionic and Dianionic Forms

Monosulfonated Azo Dyes: A Crystallographic Study of the Molecular Structures of the Free Acid, Anionic and Dianionic Forms

Adding Only One Priority Rule Allows Extending CIP Rules to Supramolecular Systems

Layered Inorganic–Organic 3,5-Dimethylpyrazole-4-Sulfonate Films for Protection of Copper Surfaces against Corrosion

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