Lock‐And‐Key Processes at Crystalline Interfaces: Relevance to the Spontaneous Generation of Chirality

Weissbuch, Isabelle; Popovitz‐Biro, Ronit; Leiserowitz, Leslie; Lahav, Meir

doi:10.1002/9780470511411.ch6

Cited by 25 publications

(23 citation statements)

References 67 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A consequence of chiral recognition of enantiomeric additive molecules at the enantiotopic faces of centrosymmetric crystal has been observed not only during growth but also during crystal dissolution, as illustrated by the formation of enantiomorphous etch‐pits at the {010} faces of α‐gly crystals dissolved in the presence of enantiopure α‐amino acids except proline, Figure 6 10. 11…”

Section: “Mirror‐symmetry Breaking” With Organic Centrosymmetric Cmentioning

confidence: 99%

Achiral Organic, Inorganic, and Metal Crystals as Auxiliaries for Asymmetric Transformations

Weissbuch¹,

Leiserowitz²,

Lahav³

2011

Israel Journal of Chemistry

Self Cite

View full text Add to dashboard Cite

The use of achiral crystalline architectures as intermediate auxiliaries for the performance of “absolute” asymmetric transformations is reviewed. Such architectures are delineated, in some cases, by pairs of homochiral surfaces of opposite handedness. This phenomenon is more common among organic crystals that frequently appear in triclinic, monoclinic, orthorhombic, or tetragonal space groups. Consequently, the chiral surfaces of such crystals have been shown to display enantiomeric recognition for molecules of the environment, a process that has been instrumental in the conversion of achiral host crystals into enantiomorphous solid‐solutions, for a successful performance of “absolute” asymmetric transformations and for the control of crystal polymorphism. Mixed crystals of reduced symmetry display properties such as second harmonic generation or pyroelectricity. On the other hand, achiral faces delineate metals, which crystallize in cubic space‐groups of high symmetry. However, by slicing such crystals in particular directions, they might express homochiral high Miller index faces that contain homochiral kink sites, which have been successfully exploited in electrochemical separations of sugars and for the resolution of enantiomers by enantioselective desorption. Representative examples of each class of materials are described.

show abstract

Section: “Mirror‐symmetry Breaking” With Organic Centrosymmetric Cmentioning

confidence: 99%

Achiral Organic, Inorganic, and Metal Crystals as Auxiliaries for Asymmetric Transformations

Weissbuch¹,

Leiserowitz²,

Lahav³

2011

Israel Journal of Chemistry

Self Cite

View full text Add to dashboard Cite

show abstract

“…g glycine can be formed from acidic or basic aqueous solution, because at high or low pH, the zwitterions become protonated or de-protonated, respectively, making cyclic dimer formation unfavourable [7]. An alternative explanation is that at high and low pH, charged glycine species inhibits the growth of a-Glycine [8]. The growth of b-Glycine from water-alcohol mixtures is thought to be due to the inhibition of the growth of both a and g glycine via specific alcohol interactions [9].…”

Section: Introductionmentioning

confidence: 96%

Gel growth of α and γ glycine and their characterization

Sankar

Manikandan

Ram

et al. 2010

Journal of Crystal Growth

View full text Add to dashboard Cite

“…"Crystal design or engineering" enables, in principle, a direct handling of the structure, size, and shape of crystals entering into the elaboration of materials [1,2]. This appears as a complex issue where several different mechanisms are involved in the control of the final crystal properties [3,4]. Classical means of controling size, morphology, and polymorphic expression of crystals make use of parameters such as temperature, pH, supersaturation, and solvent quality [5].…”

Section: Introductionmentioning

confidence: 99%