Synthesis and some features of phase behavior of chiral p-alkoxyphenyl glycerol ethers

Fayzullin, Robert R.; Antonovich, Olga A.; Zakharychev, Dmitry V.; Бредихина, З. А.; Kurenkov, A. V.; Бредихин, А. А.

doi:10.1134/s1070428015020116

Cited by 4 publications

(5 citation statements)

References 18 publications

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“…All this may indicate a similarity in the molecular microenvironment and thereby the isostructural nature of crystals of the compared phases. As discussed in the introduction, we did not observe the eutectic melting for the samples with intermediate enantiomeric compositions of diol 1 , which is not typical for conglomerate or racemic compound forming systems. On the basis of this, we hypothesize that diol 1 forms an almost ideal solid solution of the enantiomers (β-phase rac - 1 ) that is stable at high temperatures.…”

Section: Resultsmentioning

confidence: 53%

“…The synthesis of the racemic and enantiopure samples of diol 1 and the procedure of solubility experiments , were described in detail in our previous work.…”

Section: Methodsmentioning

confidence: 99%

“…Thus, we presumed that the members of the whole family of the explored glycerol derivatives, from para-methoxy-to para-nheptyloxyphenyl glycerol ether, forms a solution of enantiomers in crystalline state. 26 Interestingly, another notable group of glycerol ethers, which shows so-called preferential enrichment phenomenon, falls into a solid solution class as well. 27 In this work, we set out to investigate in depth the nature of the racemic substance, the features of phase behavior, and the crystal structure of para-methoxyphenyl glycerol ether 1, the simplest representative of the above-mentioned homologous series.…”

Section: ■ Introductionmentioning

confidence: 99%

“…At the same time, we did not observe the eutectic melting of the samples of intermediate composition. Thus, we presumed that the members of the whole family of the explored glycerol derivatives, from para -methoxy- to para - n -heptyloxyphenyl glycerol ether, forms a solution of enantiomers in crystalline state . Interestingly, another notable group of glycerol ethers, which shows so-called preferential enrichment phenomenon, falls into a solid solution class as well …”

Section: Introductionmentioning

confidence: 99%

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Intricate Phase Behavior and Crystal Structure Features of Chiral para-Methoxyphenyl Glycerol Ether Forming Continuous and Partial Solid Solutions

Fayzullin

Zakharychev

Gubaidullin

et al. 2016

Crystal Growth & Design

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Heterogeneous equilibria, crystallization, and polymorphism of chiral para-methoxyphenyl glycerol ether 1 have been inspected, and, as a result, the binary phase diagram and the Gibbs free energy vs temperature plot were constructed and analyzed. This enantiomeric system forms a stable racemic compound, which turns into an almost ideal continuous solution of the enantiomers in the crystalline phase at elevated temperatures. At room temperature the system represents a stoichiometric racemic compound and two symmetrical eutectoid invariants with partial solid solutions based on the enantiomers. Crystal structures of the true racemate, the pseudoracemate, and the pure enantiomer were investigated by single crystal X-ray diffraction. The true racemate crystallizes in the Pc space group with Z′ = 2. The pseudoracemate was solved in the Pbcn group with the only independent molecule equally disordered into two mirror-related positions. The enantiomeric crystals belong to the P21212 group and are characterized by six symmetry independent molecules (Z′ = 6), two of which undergo disordering. We also discussed possible connection between the phase behavior features and the details of the crystal structure, in particular, bilayer supramolecular organization, pseudosymmetry, high Z′, and disordered packing. General considerations about the crystalline nature of solid solutions of enantiomers were also made.

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Section: Resultsmentioning

confidence: 53%

“…The synthesis of the racemic and enantiopure samples of diol 1 and the procedure of solubility experiments , were described in detail in our previous work.…”

Section: Methodsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Intricate Phase Behavior and Crystal Structure Features of Chiral para-Methoxyphenyl Glycerol Ether Forming Continuous and Partial Solid Solutions

Fayzullin

Zakharychev

Gubaidullin

et al. 2016

Crystal Growth & Design

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“…This involves comparing compounds within a kindred or homologous series of chiral substances. [29][30][31][32][33][34][35] Comparison of the energy characteristics of crystal phases with the features of their crystal structures, as determined by X-ray diffraction, can also provide valuable information for this assessment.…”

Section: Introductionmentioning

confidence: 99%

Solubility- and melting-based approaches to evaluate the inner-crystal enantiophobia and enantiophilia undergoing a structural change within a homologous series, exemplified by chiral glycerol ethers

Zakharychev,

Fayzullin

2024

CrystEngComm

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Structural aspects of partial solid solution formation: two crystalline modifications of a chiral derivative of 1,5-dihydro-2H-pyrrol-2-one under consideration

et al. 2017

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The purposeful change of crystallization conditions for rac-3-chloro-5-hydroxy-1-(4-methylbenzyl)-4-[(4-methylphenyl)sulfanyl]-1,5-dihydro-2H-pyrrol-2-one 1 leads to two different crystal modifications, namely, a racemic compound in the triclinic space group P1 with Z′ = 1 (α-1) and a partial solid solution based on a racemic compound in the monoclinic space group P2 1 with Z′ = 4 (β-1). The first modification, α-1, is characterized by a higher density of the molecular packing in the crystal, while the second one, β-1, by a stronger system of hydrogen bonds and the presence of positional and substitutional disorder simultaneously.The analysis of the crystal structure of modifications α and β allowed us to define some structural aspects of the partial solid solution formation. Namely, the tendency to build a stronger hydrogen bond system enables the solution of enantiomers of 1 to be formed in the crystalline phase, whereas the propensity of the molecules to adopt a more favorable transoid conformation limits the solubility of the minor enantiomer.

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Synthesis and some features of phase behavior of chiral p-alkoxyphenyl glycerol ethers

Cited by 4 publications

References 18 publications

Intricate Phase Behavior and Crystal Structure Features of Chiral para-Methoxyphenyl Glycerol Ether Forming Continuous and Partial Solid Solutions

Intricate Phase Behavior and Crystal Structure Features of Chiral para-Methoxyphenyl Glycerol Ether Forming Continuous and Partial Solid Solutions

Solubility- and melting-based approaches to evaluate the inner-crystal enantiophobia and enantiophilia undergoing a structural change within a homologous series, exemplified by chiral glycerol ethers

Structural aspects of partial solid solution formation: two crystalline modifications of a chiral derivative of 1,5-dihydro-2H-pyrrol-2-one under consideration

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