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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...
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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.
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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.
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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...
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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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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.
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Chiral inheritance effect in the reactive cystine-based coassembly system.

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This summary is machine-generated.

Researchers developed efficient condensed-state reactions in self-assemblies using aromatic cystine derivatives. This enables controlled molecular rearrangement and cascade reactions, impacting nanoarchitecture structures and chiral expression.

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Area of Science:

  • Materials Science
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Controlled chemical reactions are crucial for smart material design.
  • Reactions in condensed states are typically less efficient than in solution due to limited diffusion and molecular collisions.

Purpose of the Study:

  • To investigate templating effects in self-assemblies undergoing multiple reactions.
  • To achieve efficient chemical transformations in the solid or aggregated state.
  • To explore chiral expression and inheritance in topochemical evolutions.

Main Methods:

  • Utilized an aromatic cystine derivative to form self-assemblies.
  • Triggered disulfide bond cleavage and subsequent molecular rearrangement using a reductant.
  • Incorporated a guest molecule (pentafluoropyridine) for cascade reactions via π-hole/π interactions.

Main Results:

  • Achieved quantitative disulfide bond cleavage and molecular rearrangement in aggregates.
  • Demonstrated an efficient cascade two-step reaction (reduction and nucleophilic substitution) in the condensed state.
  • Observed templating and inheritance of macroscopic chiral expression and chiroptical activities.

Conclusions:

  • Introduced a new class of efficient reactions in self-assembled states with flexible guest control.
  • Unveiled the chiral inheritance effect in topochemical evolutions within self-assembled systems.
  • Highlighted the potential for designing advanced smart materials through controlled condensed-state reactions.