Hydrogen-bond patterns and the structures of 1,4-cyclohexanediol: 2:1 <i>cis</i>:<i>trans</i>-1,4-cyclohexanediol

Loehlin, James H.; Lee, Michelle; Woo, Christina M.

doi:10.1107/s0108768108019460

Cited by 3 publications

(2 citation statements)

References 17 publications

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“…For the pure enantiomeric forms of trans -1,2-cyclohexanediol, a crystalline structure belonging to the hexagonal system, made up of biequatorial molecules, and a metastable phase were identified . An orthorhombic crystal is described for the cis -1,2-isomer, and a cubic plastic crystal phase, enantiotropically related to the crystalline one, was also identified. , For 1,4-cyclohexanediols, a 2:1 cis:trans cocrystal was recently described in which the trans isomer is present as the biequatorial conformer …”

Section: Introductionmentioning

confidence: 98%

“…7,8 For 1,4-cyclohexanediols, a 2:1 cis:trans cocrystal was recently described in which the trans isomer is present as the biequatorial conformer. 12 In this work, following our interest in cyclohexane derivatives, a search for trans-1,4-cyclohexanediol polymorphic forms was carried out taking the pure compound as the starting material, and its thermal behavior was investigated from room temperature to fusion.…”

Section: Introductionmentioning

confidence: 99%

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Polymorphism of trans-1,4-Cyclohexanediol: Conformational Isomorphism

Maria

Castro

Bebiano

et al. 2010

Crystal Growth & Design

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In this work, an investigation on the polymorphism of trans-1,4-cyclohexanediol is performed. Polymorph screening is carried out by crystallization from solutions, by sublimation, and by cooling the melt, and a combined approach using differential scanning calorimetry, polarized light thermomicroscopy, and X-ray diffraction is employed in the results interpretation. Three solid forms, I, II, and III (Steiner et al. J. Chem. Soc., Perkin Trans. 2 1998, 371−377), are identified, I and II, for the first time, and their relative stability established. The crystal structure of polymorph II is resolved by single crystal X-ray diffraction: a monoclinic P21/a space group structure. This polymorph, as polymorph III (Steiner et al. J. Chem. Soc., Perkin Trans. 2 1998, 371−377), exhibits unusual conformational isomorphism, that is, the coexistence of the biequatorial and the biaxial conformers in the same crystal structure.

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Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Polymorphism of trans-1,4-Cyclohexanediol: Conformational Isomorphism

Maria

Castro

Bebiano

et al. 2010

Crystal Growth & Design

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Failures of fractional crystallization: ordered co-crystals of isomers and near isomers

Kelley

Fábián

Brock

2011

Acta Crystallogr B Struct Sci

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A list of 270 structures of ordered co-crystals of isomers, near isomers and molecules that are almost the same has been compiled. Searches for structures containing isomers could be automated by the use of IUPAC International Chemical Identifier (InChI™) strings but searches for co-crystals of very similar molecules were more labor intensive. Compounds in which the heteromolecular A···B interactions are clearly better than the average of the homomolecular A···A and B···B interactions were excluded. The two largest structural classes found include co-crystals of configurational diastereomers and of quasienantiomers (or quasiracemates). These two groups overlap. There are 114 co-crystals of diastereomers and the same number of quasiracemates, with 71 structures being counted in both groups; together the groups account for 157 structures or 58% of the total. The large number of quasiracemates is strong evidence for inversion symmetry being very favorable for crystal packing. Co-crystallization of two diastereomers is especially likely if a 1,1 switch of a methyl group and an H atom, or of an inversion of a [2.2.1] or [2.2.2] cage, in one of the diastereomers would make the two molecules enantiomers.

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Threefold helical assembly via hydroxy hydrogen bonds: the 2:1 co-crystal of bicyclo[3.3.0]octane-endo-3,endo-7-diol and bicyclo[3.3.0]octane-endo-3,exo-7-diol

Chan¹,

Bhadbhade²,

Bishop³

2021

Acta Cryst E

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Reduction of bicyclo[3.3.0]octane-3,7-dione yields a mixture of the endo-3,endo-7-diol and endo-3, exo-7-diol (C8H14O2) isomers (5 and 6). These form (5)2·(6) co-crystals in the monoclinic P21/n space group (with Z = 6, Z′ = 1.5) rather than undergoing separation by means of fractional recrystallization or column chromatography. The molecule of 5 occupies a general position, whereas the molecule of 6 is disordered over two orientations across a centre of symmetry with occupancies of 0.463 (2) and 0.037 (2). Individual diol hydroxy groups associate around a pseudo-threefold screw axis by means of hydrogen bonding. The second hydroxy group of each diol behaves in a similar manner, generating a three-dimensional hydrogen-bonded network structure. This hydrogen-bond connectivity is identical to that present in three known helical tubuland diol–hydroquinone co-crystals, and the new crystal structure is even more similar to two homologous aliphatic diol co-crystals.

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Hydrogen-bond patterns and the structures of 1,4-cyclohexanediol: 2:1 cis:trans-1,4-cyclohexanediol

Cited by 3 publications

References 17 publications

Polymorphism of trans-1,4-Cyclohexanediol: Conformational Isomorphism

Polymorphism of trans-1,4-Cyclohexanediol: Conformational Isomorphism

Failures of fractional crystallization: ordered co-crystals of isomers and near isomers

Threefold helical assembly via hydroxy hydrogen bonds: the 2:1 co-crystal of bicyclo[3.3.0]octane-endo-3,endo-7-diol and bicyclo[3.3.0]octane-endo-3,exo-7-diol

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