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Related Concept Videos

Chirality02:25

Chirality

28.7K
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...
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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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Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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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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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...
4.7K
Chirality in Nature02:30

Chirality in Nature

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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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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Inherently Chiral Bambus[4]urils.

Amar Ramchandra Mohite1, Ofer Reany1

  • 1Department of Natural Sciences, The Open University of Israel, Ra'anana 4353701, Israel.

The Journal of Organic Chemistry
|June 12, 2020
PubMed
Summary
This summary is machine-generated.

Researchers designed new asymmetric bambusurils (BU[4]s) with unique chiral properties. These novel macrocycles were characterized, revealing four possible diastereoisomers and enabling effective enantiomeric separation and analysis using NMR spectroscopy.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Stereochemistry

Background:

  • Bambusurils (BU[4]s) are macrocyclic compounds with potential applications in molecular recognition.
  • Previous studies focused on symmetric BU[4]s, limiting exploration of stereoisomeric diversity.
  • Asymmetric substitution offers a route to novel chiral architectures within the BU[4] framework.

Purpose of the Study:

  • To design and synthesize a new class of asymmetric bambusurils (BU[4]s) with varying N-alkyl substituents.
  • To characterize the structural and stereochemical properties of these novel BU[4]s.
  • To develop and apply methods for resolving and analyzing chiral BU[4] stereoisomers.

Main Methods:

  • Synthesis of asymmetric N,N'-disubstituted glycoluril subunits.
  • Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy and X-ray crystallography.
  • Chiral High-Performance Liquid Chromatography (HPLC) for enantiomeric separation.
  • 1H NMR spectroscopy with (R)-BINOL as a chiral solvating agent for enantiopurity analysis.

Main Results:

  • Successful synthesis and full characterization of asymmetric bambusurils (BU[4]s).
  • Identification of four possible macrocyclic diastereoisomers: two achiral and two inherently chiral.
  • X-ray crystallography confirmed the influence of N-substituent arrangement on macrocycle symmetry.
  • Chiral HPLC resolved Pr4Me4BU[4] into its enantiomers.
  • NMR spectroscopy with a chiral solvating agent effectively observed all four inherently chiral BU[4] pairs.

Conclusions:

  • Asymmetric substitution in bambusurils leads to the formation of inherently chiral macrocycles.
  • NMR spectroscopy with chiral solvating agents provides a rapid and powerful method for assessing enantiopurity in chiral cavitands.
  • This approach complements traditional chromatographic techniques for chiral analysis.