Chirality in adsorption on solid surfaces
1Department of Chemistry and UCR Center for Catalysis, University of California, Riverside, CA 92521, USA. zaera@ucr.edu.
Chemical Society Reviews
|October 19, 2017
Summary
This review explores recent advances in understanding chemical chirality at solid surfaces. Key phenomena like surface reconstruction and enantioselectivity are discussed, offering insights into chiral molecule adsorption and surface modification.
Area of Science:
- Surface Chemistry
- Chirality Studies
- Materials Science
Background:
- Chirality is fundamental to life's biochemistry.
- Solid surfaces play a crucial role in many chiral chemical reactions.
- Understanding surface chirality is vital for applications in synthesis and separation.
Purpose of the Study:
- To review recent advances in chemical chirality at solid surfaces.
- To describe methods for bestowing chirality onto surfaces.
- To analyze molecular-level adsorption of chiral compounds.
Main Methods:
- Surveying literature on adsorption of enantiomers, enantiomeric mixtures, and prochiral molecules.
- Examining studies on model surfaces like metal single crystals and graphite.
- Analyzing phenomena such as surface reconstruction and chiral imprinting.
Main Results:
- Identified phenomena include surface reconstruction and chiral imprinting.
- Observed enhancement or suppression of enantioselectivity in adsorbed layers.
- Discussed methods for creating enantioselective surface sites via supramolecular ensembles or adsorbate:modifier adducts.
Conclusions:
- Surface chirality significantly influences adsorption and reactivity of chiral molecules.
- Strategies for creating enantioselective surfaces are advancing.
- The liquid phase impacts enantioselective processes like crystallization and catalysis.
Related Concept Videos
Chirality
30.0K
Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
30.0K
Chirality in Nature
17.4K
Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
17.4K
Prochirality
5.1K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
5.1K
Molecules with Multiple Chiral Centers
15.3K
Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
15.3K
Chirality at Nitrogen, Phosphorus, and Sulfur
7.1K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
7.1K
Analyte Adsorption and Distribution
2.9K
In certain chromatographic separations, solutes transfer between the mobile phase and the stationary phase via sorption, which typically refers to the process of adsorption. For many chromatographic systems, the sorption process often depends on the polarity of the compounds—an expression of the overall dipole moment within the molecule. During the separation process, there is competition between the solute and solvent for adsorption to the stationary phase. Highly polar compounds and...
2.9K


