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Related Concept Videos

Prochirality02:05

Prochirality

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...
Chirality02:25

Chirality

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...
Chirality in Nature02:30

Chirality in Nature

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. The...
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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...
Naming Enantiomers02:21

Naming Enantiomers

The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three steps:...
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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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A Micropatterning Assay for Measuring Cell Chirality
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Development of an axial chirality switch.

Stefan Reichert1, Bernhard Breit

  • 1Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität Freiburg i. Brsg., Albertstr. 21, 79104 Freiburg i. Brsg., Germany.

Organic Letters
|February 8, 2007
PubMed
Summary

Researchers developed a novel axial chiral system exhibiting solvent-dependent atropisomerism. The study demonstrates precise control over axial chirality through strategic solvent selection, confirmed by spectroscopy.

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Area of Science:

  • Organic Chemistry
  • Stereochemistry

Background:

  • Axial chirality is a key stereochemical concept.
  • Controlling atropisomerism in molecular systems is challenging.

Purpose of the Study:

  • To develop and synthesize a new axial chiral system.
  • To investigate solvent-dependent atropisomerism.
  • To demonstrate control of axial chirality via solvent choice.

Main Methods:

  • Synthesis of a novel axial chiral compound.
  • Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Circular Dichroism (CD) spectroscopy.

Main Results:

  • Successful development and synthesis of the new axial chiral system.
  • Demonstration of solvent-dependent atropisomerism.
  • Confirmation of axial chirality control by solvent selection.

Conclusions:

  • The new system exhibits controllable axial chirality.
  • Solvent choice is a viable strategy for modulating atropisomerism.
  • NMR and CD spectroscopy are effective tools for studying such systems.