The crystal structure of the triclinic modification of quinhydrone

Sakurai, Tosio

doi:10.1107/s0365110x65003390

Cited by 96 publications

(66 citation statements)

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“…However, the quinhydrone molecule is a molecular complex between p-benzoquinone (BQ) and hydroquinone (H 2 Q) (Scheme 1). Its structure reveals the formation of regular alternate donor/acceptor stacks [15,16], while infinite molecular chains form through hydrogen bonds between the hydroxyl and the carbonyl groups. The chemical conversion of H 2 Q to quinhydrone involves electron transfer coupled with proton transfer [17].…”

Section: Introductionmentioning

confidence: 99%

Self-assembled calix[4]arenequinhydrone on the platinum electrode by cathodic reduction of calix[4]arenediquinone

Youchret-Zallez¹,

Besbes-Hentati²,

Bouvet

et al. 2011

J Incl Phenom Macrocycl Chem

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The electrochemical reduction of di(methoxyp-tert-butyl)calix [4]arenediquinone led to its calix[4]arenedihydroquinone. The presence of both in the solution refers to the generation of calix[4]arenequinhydrone charge-transfer complex at the electrode surface through a donor/acceptor process type. Self-assembled adlayers of calix[4]arenequinhydrone was obtained by partial electrochemical reduction. Electrochemical deposition of the last form was achieved on the platinum disk electrode at -1.16 V versus SCE (saturated calomel electrode) in aprotic solution by cathodic reduction of the starting substrate. The deposit was first characterized by cyclic voltammetry (CV) in electrolytic solution and then in electrolyte support solution and finally in a ferricyannure solution. The self-assembled product was characterized by MALDI-TOF Mass and IR spectroscopy techniques. It was observed too by SEM technique. Calix[4]arenequinhydrone is observed on the electrode surface as hexangular prisms with a length of few micrometers.

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Section: Introductionmentioning

confidence: 99%

Self-assembled calix[4]arenequinhydrone on the platinum electrode by cathodic reduction of calix[4]arenediquinone

Youchret-Zallez¹,

Besbes-Hentati²,

Bouvet

et al. 2011

J Incl Phenom Macrocycl Chem

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“…A least-squares refinement which adopted only this one shift converged to an R of 12.3% for the 200 reflexions, and the structure reported by T. Sakurai with the origin shifted by a/2 was obtained. A second least-squares refinement which adopted a +0.2 A shift in the x coordinate of O(1), corresponding to the second lowest R in Ta/cle 1, also led to the correct structure with the same origin as defined by T. Sakurai (1965).…”

Section: R(x) R(y) R(z)mentioning

confidence: 89%

“…The key shift method was first applied to a known structure, triclinic quinhydrone (T. Sakurai, 1965), and then to an unknown structure, 3-amino-4,5-dicyano-l-methylpyrazole (ADCMP) (Prusiner, Sundaralingam, Ito & Sakurai, 1976).…”

Section: Applicationmentioning

confidence: 99%

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The key shift method. II. Application to superstructures of molecular crystals

Ito¹

1976

Acta Crystallogr Sect B

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The key shift method, a kind of minimum residual method, has been successfully applied to the structure analysis of superstructures, one known and one unknown, of molecular crystals with eight and eleven non-hydrogen atoms respectively in the asymmetric units. In the latter case, symmetry considerations of the substructure-superstructure relationship were important for the solution. In another case of a known superstructure in which there were 30 independent non-hydrogen atoms at the start of the analysis, shifts of rigid-body molecules were found to be more efficient than those of individual atoms.

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“…Cet arrangement alternant de molecules/t caract~re donneur et molecules fi caract~re accepteur se retrouve dans les structures monocliniques et tricliniques de la quinhydrone, complexe entre la p-benzoquinone et l'hydroquinone (Sakurai, 1965(Sakurai, , 1968 (Hartmann & Perdok, 1952) dont la direction moyenne est [201]. Ces liaisons d'6nergie notable (2,73 /~,) au nombre de deux par mol6cule assurent au cristal une forte coh6sion dans la direction consid6r6e.…”

Section: Donndes Cristallographiquesunclassified

Structure cristalline de complexes moléculaires en série naphtoquinonique. I. Structure du complexe 1:1 entre la naphtoquinone-1,4 et l'hydroquinone

Thozet¹,

Gaultier²

1977

Acta Crystallogr Sect B

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The crystal of the molecular complex between hydroquinone and 1,4~naphthoquinone is orthorhombic, space group P2~212 ~, with a = 6.145 (2), b = 26.820 (4), c = 7.768 (2) A, Z = 4. The structure has been determined by direct methods and refined to R = 0.047 for the 1376 reflexions recorded with an automatic singlecrystal diffractometer. The molecular structure of each component shows no difference from that found in the pure complex product. The structure appears in the form of 'molecular sheets' parallel to the (010) plane and linked by van der Waals bonds. In a sheet along the [001 ] direction, there are alternate hydroquinone and naphthoquinone molecules bound to each other. The molecules are almost parallel. The C=O group of naphthoquinone is over the phenyl ring of hydroquinone and the OH group of hydroquinone is over the primary ring of naphthoquinone (distance of about 3-2 A). There are very strong interactions between these two molecules and hydrogen bonds between these columns along the [201 ] direction. Each molecule of one species is bound to two molecules of the other species (O. • -O = 2.73 A).

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The crystal structure of the triclinic modification of quinhydrone

Cited by 96 publications

References 1 publication

Self-assembled calix[4]arenequinhydrone on the platinum electrode by cathodic reduction of calix[4]arenediquinone

Self-assembled calix[4]arenequinhydrone on the platinum electrode by cathodic reduction of calix[4]arenediquinone

The key shift method. II. Application to superstructures of molecular crystals

Structure cristalline de complexes moléculaires en série naphtoquinonique. I. Structure du complexe 1:1 entre la naphtoquinone-1,4 et l'hydroquinone

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