Structure of (–)-quinic acid

Abell, C.; Allen, Frank H.; Bugg, Timothy D. H.; Doyle, Michael J.; Raithby, P. R.

doi:10.1107/s0108270188002884

Cited by 12 publications

(11 citation statements)

References 5 publications

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“…In (I) ( Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Abell et al, 1988). The cyclohexane ring (C1-C6) adopts a chair conformation.…”

Section: Data Collectionsupporting

confidence: 90%

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1-Hydroxycyclohexanecarboxylic acid

Yang

et al. 2007

Acta Crystallogr E Struct Rep Online

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Key indicators: single-crystal X-ray study; T = 153 K; mean (C-C) = 0.002 Å; R factor = 0.032; wR factor = 0.082; data-to-parameter ratio = 13.0.The title compound, C 7 H 12 O 3 , was synthesized as an intermediate for the synthesis of the selective broad-spectrum nonsystemic acaricide spirodiclofen (trade name Envidor). The cyclohexane ring adopts a chair conformation. The molecules pack in layers, with O-HÁ Á ÁO hydrogen bonds connecting the layers on one side and only van der Waals interactions on the other side. Related literatureFor the biological activity of the title compound, see: Thomas et al. (2003). For a similar structure, see: Abell et al. (1988). Experimental Crystal data C 7 H 12 O 3 M r = 144.17 Monoclinic, P2 1 =c a = 11.790 (2) Å b = 6.7956 (14) Å c = 9.6100 (19) Å = 104.97 (3) V = 743.8 (3) Å 3 Z = 4 Mo K radiation = 0.10 mm À1 T = 153 (2) K 0.24 Â 0.13 Â 0.09 mm Data collection Rigaku R-AXIS RAPID IP area-detector diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T min = 0.917, T max = 0.991 5504 measured reflections 1303 independent reflections 1230 reflections with I > 2(I) R int = 0.022

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Section: Data Collectionsupporting

confidence: 90%

“…For the biological activity of the title compound, see: Thomas et al (2003). For a similar structure, see: Abell et al (1988). Mo K radiation = 0.10 mm À1 T = 153 (2) K 0.24 Â 0.13 Â 0.09 mm…”

Section: Related Literaturementioning

confidence: 99%

1-Hydroxycyclohexanecarboxylic acid

Yang

et al. 2007

Acta Crystallogr E Struct Rep Online

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“…1). The cyclohexanone ring adopts a chair conformation with intra-annular torsion angles in the range 49.9 (2)-58.9 (2) ° [mean 53.9 (2)°], which have the expected values (Abell et al, 1988). The attached 3-hydroxy and 4-phenyl groups are disposed in α-axial and β-equatorial configurations, respectively, while the two ethoxycarbonyl groups adopt syn configurations (Hernández-Ortega et al, 2001).…”

Section: Data Collectionmentioning

confidence: 92%

“…For the synthesis of the title compound, see: Floyd & Miller (1963). For related structures, see: Abell et al (1988); Herná ndez-Ortega et al (2001). For graph-set analysis, see: Etter et al (1990).…”

Section: Related Literaturementioning

confidence: 99%

rac-syn-Diethyl 2-hydroxy-4-oxo-1-phenylcyclohexane-1,2-dicarboxylate

Wang

Meng

2011

Acta Cryst E

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The title compound, C18H22O6, was obtained by the domino oxa–Michael–aldol (DOMA) reaction and has the cyclohexanone ring in a chair conformation with intra-annular torsion angles in the range 49.9 (2)–58.9 (2)°. The two ethoxycarbonyl substituents on the cyclohexanone ring adopt a syn configurations. In the crystal, the molecules self-assemble through duplex intermolecular hydroxy–carbonyl O—H⋯O hydrogen bonds, giving centrosymmetric cyclic dimers [graph set R 2 2(12)] which inter-associate through weak C—H⋯O hydrogen-bonding interactions.

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“…This conformation was also found in the solid state by X-ray diffraction. 28 In order to characterise the complexes formed, a proper assignment of all the proton and carbon NMR signals of the ligand is necessary, for various pH conditions. The proton and carbon chemical shifts, as well as the proton-proton coupling constants, are shown in Tables 2 and 3, for different pH values.…”

Section: Structure Of D-(؊)quinic Acid In Aqueous Solutionmentioning

confidence: 99%

NMR and X-ray diffraction studies of the complexation of D-(–)quinic acid with tungsten(vi) and molybdenum(vi)

Ramos

Pereira

Beja

et al. 2002

J. Chem. Soc., Dalton Trans.

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By using multinuclear ( 1 H, 13 C, 17 O, 95 Mo, 183 W) magnetic resonance spectroscopy (1D and 2D), quinic acid is found to form 2 homologous complexes with both tungsten() and molybdenum(), in aqueous solution. Two isomeric 1 : 2 (metal : ligand) complexes involving the carboxylate and the adjacent OH groups are present in the pH range 2-11. One of the W() complexes with quinic acid, WO 2 (C 7 H 10 O 6 ) 2 2Ϫ has been isolated in the solid state and characterised by X-ray diffraction, the tungsten atom being six-coordinated in an approximate square bipyramidal geometry. This structure is identical to that proposed for the most stable complex in solution. In the presence of hydrogen peroxide and with both metals, quinic acid forms one 1 : 1 : 2 (metal : ligand : peroxide) species, also involving the carboxylate and the adjacent OH groups.

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Structure of (–)-quinic acid

Cited by 12 publications

References 5 publications

1-Hydroxycyclohexanecarboxylic acid

1-Hydroxycyclohexanecarboxylic acid

rac-syn-Diethyl 2-hydroxy-4-oxo-1-phenylcyclohexane-1,2-dicarboxylate

NMR and X-ray diffraction studies of the complexation of D-(–)quinic acid with tungsten(vi) and molybdenum(vi)

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