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Related Concept Videos

Prochirality02:05

Prochirality

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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons00:58

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

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Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
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Stereoisomerism02:52

Stereoisomerism

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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
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Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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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.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
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A Bifunctional Coordination-Chain-Based Hydrogen-Bonded Framework for Quantitative Enantioselective Sensing.

Zongsu Han1, Mengmeng Wang1, Kunyu Wang1

  • 1Department of Chemistry, Key Laboratory of Advanced Energy Materials Chemistry (MOE) and, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 27, 2023
PubMed
Summary

This study presents a new method for enantioselective sensing using a coordination-chain-based framework. This approach enables rapid detection of enantiomers, overcoming challenges in distinguishing similar chemical compounds.

Keywords:
chiral cation exchangecoordination chainenantioselective sensinghydrogen-bonded frameworkquantitative recognition

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Area of Science:

  • Materials Science
  • Analytical Chemistry
  • Supramolecular Chemistry

Background:

  • Enantioselective sensing is critical due to differing biological impacts of enantiomers.
  • Luminescent coordination compounds offer tunable properties for sensing applications.
  • Direct synthesis of chiral, luminescent materials is difficult and costly.

Purpose of the Study:

  • To develop a facile method for creating bifunctional frameworks for enantioselective sensing.
  • To utilize a coordination-chain-based hydrogen-bonded framework as a host for chiral and luminescent centers.
  • To enable high-performance enantioselective sensing of enantiomer mixtures.

Main Methods:

  • A cation exchange reaction was employed to incorporate chiral and luminescent centers into an anionic coordination-chain-based hydrogen-bonded framework.
  • The resulting bifunctional framework was characterized for its sensing capabilities.
  • The framework's ability to distinguish between enantiomers was evaluated.

Main Results:

  • A bifunctional framework with enantioselective sensing properties was successfully synthesized.
  • The host-guest approach via cation exchange proved effective in creating the desired material.
  • The framework demonstrated the ability to sense mixtures of enantiomers.

Conclusions:

  • Anionic coordination-chain-based hydrogen-bonded frameworks can serve as effective hosts for developing bifunctional sensing materials.
  • Facile cation exchange offers a viable strategy for constructing multifunctional frameworks.
  • This work provides a new pathway for rapid enantioselective sensing applications.