When in the presence of the strong hydrogen bonds, the weak hydrogen bonds gain an importance

Białońska, Agata; Ciunik, Zbigniew

doi:10.1039/b515365d

Cited by 32 publications

(37 citation statements)

References 33 publications

(17 reference statements)

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“…30,31 However, the inclusion crystals with 3,7,8,12,13,14,15,24,29, and 35 have a 32 and pantolactone. 33 All the resultant crystals could be categorized into three structural types of supramolecular isomers composed of common 2 1 helical tape-like assemblies stabilized by weak multiple hydrogen bonds, such as CH/O and CH/ interactions: 29 C10-HÁÁÁO3, C11-HÁÁÁO4 (O3 and O4: methoxy), C23-HÁÁÁO2 (O2: ether), and C20-HÁÁÁ (arene) hydrogen bonds as shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…34 Actually, the same molecular conformation has been observed in all known crystals of brucine, 30 brucine solvates, 30,31,34 brucine complexes, 32,33,[35][36][37] and brucinium salts. [19][20][21][22][23][24][25][26][27][28][29][38][39][40][41][42][43][44][45] Such a conformer of brucine was observed in all the resultant crystals with aliphatic alcohols with no exception. Therefore, it may be assumed that brucine molecule exists in solution as a predominant conformer.…”

Section: Resultsmentioning

confidence: 99%

“…The motifs are stabilized by weak hydrogen bonds, such as CH/O and CH/ interactions. 29 However, to our knowledge, the supramolecular isomerism of the host frameworks of brucine has been discussed ambiguously. Because of these aspects, brucine is a good starting point for extending the applicability of the hierarchical structural analysis to better understand supramolecular isomerism.…”

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confidence: 99%

“…[19][20][21][22][23][24][25][26][27][28][29] According to the studies performed by Gould and Walkinshaw,19,24 brucine forms a characteristic corrugated monolayer sheet as a motif common to its many inclusion crystals, in spite of appearance of supramolecular isomeric host frameworks. The motifs are stabilized by weak hydrogen bonds, such as CH/O and CH/ interactions.…”

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confidence: 99%

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Guest-Induced Supramolecular Isomerism and Chirality of Brucine Inclusion Crystals with Aliphatic Alcohols: A Hierarchical Interpretation

Watabe¹,

Kobayashi²,

Hisaki³

et al. 2007

Bulletin of the Chemical Society of Japan

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Cocrystallization of brucine with a series of aliphatic alcohols was systematically investigated to understand molecular recognition through supramolecular isomerism and chirality. Guest-induced supramolecular isomers of brucine were obtained by cocrystallization and were categorized into three structural types based on the common 2 1 helical tapelike assemblies. These supramolecular isomers were elucidated from the molecular structures on the basis of qualitative hierarchical structural analysis through supramolecular chirality. Moreover, it was found that the supramolecular isomerization occurred depending on the size of the guest molecules. This dependence was clearly evaluated on the relationship between the volume of the guest molecules and the packing coefficient of the void spaces in the host cavities.Crystalline host compounds have attracted much attention in the field of crystal engineering and supramolecular chemistry due to practical and fundamental applications in catalysis, magnetism, electro and non-linear optics, chemical separation, gas-storage, and drug delivery.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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confidence: 99%

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Guest-Induced Supramolecular Isomerism and Chirality of Brucine Inclusion Crystals with Aliphatic Alcohols: A Hierarchical Interpretation

Watabe¹,

Kobayashi²,

Hisaki³

et al. 2007

Bulletin of the Chemical Society of Japan

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“…These studies focus on using molecules with internal dipole moments to localize increased electron density and thus charge on molecular surfaces [1][2][3][4][5][6][7]. Systems of this type can be useful not only for fundamental research but also in the design of advanced materials.…”

Section: Introductionmentioning

confidence: 99%

Electron Localization on Molecular Surfaces by Metal Adsorption

Jalbout¹,

Seligman²

2009

Jnl of Comp & Theo Nano

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Abstract:The ability of metal adsorption to transfer charge to the surface of single molecular carbon sheets is explored in this paper. Though other metals are considered we basically will deal with Lithium We concentrate on fairly small sheets and examined the minimum threshold size of a molecular surface needed to separate metals. From our quantum chemical calculations we deduce that a molecular surface of six benzene rings is needed for Lithium dimers to be separated. We further observe symmetry breaking, when two lithium atoms are adsorbed right opposite to each other on the two sides of the sheet.

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Resolution of sertraline with (R)‐mandelic acid: Chiral discrimination mechanism study

Rohani

Zhu

et al. 2011

Chirality

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The chiral discrimination mechanism in the resolution of sertraline with mandelic acid was investigated by examining the weak intermolecular interactions (such as hydrogen bond, CH/π, and van der Waals interactions) and molecular packing difference in crystal structures of the resulting diastereomeric salts. A new one-dimensional chain-like hydrogen-bonding network and unique supramolecular packing mode are disclosed. The investigation demonstrated that stable hydrogen-bonding pattern, herringbone-like arrangement of aromatic rings, and planar boundary surface in the hydrophobic region are the three most important structural characteristics expected in less soluble diastereomeric salts. The existence and magnitude of hydrogen bond, CH/π interaction, and van der Waals interaction related to three characteristic structures, determine the stability of diastereomeric salt. The hydrogen bond is not necessarily the dominant factor while the synergy and optimization of all weak intermolecular interactions attribute to the chiral recognition.

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When in the presence of the strong hydrogen bonds, the weak hydrogen bonds gain an importance

Cited by 32 publications

References 33 publications

Guest-Induced Supramolecular Isomerism and Chirality of Brucine Inclusion Crystals with Aliphatic Alcohols: A Hierarchical Interpretation

Guest-Induced Supramolecular Isomerism and Chirality of Brucine Inclusion Crystals with Aliphatic Alcohols: A Hierarchical Interpretation

Electron Localization on Molecular Surfaces by Metal Adsorption

Resolution of sertraline with (R)‐mandelic acid: Chiral discrimination mechanism study

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