The crystal and molecular structure of hydroxyquinones and salts of hydroxyquinones. V. Hydronium nitranilate, nitranilic acid hexahydrate

Andersen, E. Krogh

doi:10.1107/s0365110x67000362

Cited by 16 publications

(11 citation statements)

References 5 publications

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“…When using the [M III (acac 2 (38), have been prepared and characterized by Coronado et al [172]. The 2D anilate-based networks show the common honeycomb anionic packing pattern but a novel type of structure where the cations are placed into the hexagonal channels of the 2D network has been afforded due to the smaller size of the [Fe III (acac 2 -trien)] + or [Ga III (acac 2 -trien)] + complex with respect to the templating cations used in previous compounds of this type, where they are placed in between the anionic layers.…”

Section: Spin-crossover Complexesmentioning

confidence: 99%

Recent Advances on Anilato-Based Molecular Materials with Magnetic and/or Conducting Properties

et al. 2017

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Abstract:The aim of the present work is to highlight the unique role of anilato-ligands, derivatives of the 2,5-dioxy-1,4-benzoquinone framework containing various substituents at the 3 and 6 positions (X = H, Cl, Br, I, CN, etc.), in engineering a great variety of new materials showing peculiar magnetic and/or conducting properties. Homoleptic anilato-based molecular building blocks and related materials will be discussed. Selected examples of such materials, spanning from graphene-related layered magnetic materials to intercalated supramolecular arrays, ferromagnetic 3D monometallic lanthanoid assemblies, multifunctional materials with coexistence of magnetic/conducting properties and/or chirality and multifunctional metal-organic frameworks (MOFs) will be discussed herein. The influence of (i) the electronic nature of the X substituents and (ii) intermolecular interactions i.e., H-Bonding, Halogen-Bonding, π-π stacking and dipolar interactions, on the physical properties of the resulting material will be also highlighted. A combined structural/physical properties analysis will be reported to provide an effective tool for designing novel anilate-based supramolecular architectures showing improved and/or novel physical properties. The role of the molecular approach in this context is pointed out as well, since it enables the chemical design of the molecular building blocks being suitable for self-assembly to form supramolecular structures with the desired interactions and physical properties.Keywords: benzoquinone derivatives; molecular magnetism; multifunctional molecular materials; spin-crossover materials; metal-organic frameworks General IntroductionThe aim of the present work is to highlight the key role of anilates in engineering new materials with new or improved magnetic and/or conducting properties and new technological applications. Only homoleptic anilato-based molecular building blocks and related materials will be discussed. Selected examples of para-/ferri-/ferro-magnetic, spin-crossover and conducting/magnetic multifunctional materials and MOFs based on transition metal complexes of anilato-derivatives, on varying the substituents at the 3,6 positions of the anilato moiety, will be discussed herein, whose structural features or physical properties are peculiar and/or unusual with respect to analogous compounds reported in the literature up to now. Their most appealing technological applications will be also reported.

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Section: Spin-crossover Complexesmentioning

confidence: 99%

Recent Advances on Anilato-Based Molecular Materials with Magnetic and/or Conducting Properties

et al. 2017

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“…In the previous X-ray study of hydronium nitranilate (Andersen, 1967a) the hydrogen-atom positions were not determined. Since all the hydrogen atoms in the water molecules have more than two oxygen …”

Section: The Crystal Structurementioning

confidence: 98%

“…4 of Andersen, 1967a). The columns are surrounded on all sides by water molecules and hydronium ions.…”

Section: The Crystal Structurementioning

confidence: 99%

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The crystal and molecular structure of hydroxyquinones and salts of hydroxyquinones. VII. Hydronium cyananilate (cyananilic acid hexahydrate) and hydronium nitranilate (a redetermination)

Andersen¹,

Andersen²

1975

Acta Crystallogr Sect B

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The refinement of hydronium nitranilate was based on full three-dimensional Mo data (1031 reflexions were observed, that is 52 % of those in the range covered). The previous results have been confirmed. The hydrogen atoms have been located. The structure of a hydrated hydronium salt of cyananilic acid has been determined by three-dimensional diffractometer data (604 reflexions were observed, that is 71% of those in the range covered). The space group is P21/c with a=3.567, b= 19.961, c=8.927 A, fl=92.51 ° and Z=2. The ring system, which is similar to that found in salts of nitranilic acid, contains four bonds of equal lengths (1.42 A) and two considerably longer bonds (1-53 A). The carbon-oxygen bonds are of nearly equal lengths (1.24 A). The ring is planar, but the exocyclic atoms are out of this plane. The hydronium ions are linked by water molecules to form chains of composition (HTO3)n n+.

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“…Andersen (1967c) suggested that the equalization of C(2)-C(3) and C(3)-C(1') in (VIII) is brought about by disorder in the crystal. The same explanation is given for the two equal C-O bonds.…”

Section: Details Of the Structures Of Hydroxybenzoquinonesmentioning

confidence: 99%

Long bond distances betweensp²-hybridized carbon atoms. The polymethine coupling effect

Kulpe¹,

Dähne²

1978

Acta Crystallogr Sect B

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The crystal and molecular structure of hydroxyquinones and salts of hydroxyquinones. V. Hydronium nitranilate, nitranilic acid hexahydrate

Cited by 16 publications

References 5 publications

Recent Advances on Anilato-Based Molecular Materials with Magnetic and/or Conducting Properties

Recent Advances on Anilato-Based Molecular Materials with Magnetic and/or Conducting Properties

The crystal and molecular structure of hydroxyquinones and salts of hydroxyquinones. VII. Hydronium cyananilate (cyananilic acid hexahydrate) and hydronium nitranilate (a redetermination)

Long bond distances betweensp²-hybridized carbon atoms. The polymethine coupling effect

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The crystal and molecular structure of hydroxyquinones and salts of hydroxyquinones. V. Hydronium nitranilate, nitranilic acid hexahydrate

Cited by 16 publications

References 5 publications

Recent Advances on Anilato-Based Molecular Materials with Magnetic and/or Conducting Properties

Recent Advances on Anilato-Based Molecular Materials with Magnetic and/or Conducting Properties

The crystal and molecular structure of hydroxyquinones and salts of hydroxyquinones. VII. Hydronium cyananilate (cyananilic acid hexahydrate) and hydronium nitranilate (a redetermination)

Long bond distances betweensp2-hybridized carbon atoms. The polymethine coupling effect

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Long bond distances betweensp²-hybridized carbon atoms. The polymethine coupling effect