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Related Concept Videos

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,...
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...
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...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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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Related Experiment Video

Updated: Jun 12, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
09:22

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Chiral cyclotrisiloxanes.

Ryoji Tanaka1, Susumu Kowase, Masafumi Unno

  • 1Department of Chemistry and Chemical Biology, Graduate School of Engineering, Gunma University, Kiryu, Japan. polysilane@gmail.com

Dalton Transactions (Cambridge, England : 2003)
|June 24, 2010
PubMed
Summary

Chiral cyclotrisiloxanes were synthesized and separated into enantiomers for the first time. The arrangement of phenyl groups induced specific Cotton effects based on the stereochemistry of the 2-butyl substituent.

Area of Science:

  • Organosilicon Chemistry
  • Stereochemistry
  • Chiroptical Spectroscopy

Background:

  • Chiral cyclotrisiloxanes are an important class of organosilicon compounds.
  • Separation and characterization of enantiomers are crucial for understanding their properties.

Purpose of the Study:

  • To synthesize and resolve the enantiomers of chiral cyclotrisiloxanes.
  • To investigate the chiroptical properties of these novel compounds.

Main Methods:

  • Synthesis of tri(2-butyl)triphenylcyclotrisiloxane.
  • Separation of enantiomers.
  • Chiroptical spectroscopy (Cotton effect measurement).

Main Results:

  • Successful synthesis and enantiomeric separation of chiral cyclotrisiloxanes.

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  • The (R)-2-butyl enantiomer exhibited a positive Cotton effect.
  • The (S)-2-butyl enantiomer showed a negative Cotton effect.

    • Conclusions:

    • The propeller-like arrangement of phenyl groups is responsible for the observed chiroptical activity.
    • The stereochemistry of the 2-butyl group dictates the sign of the Cotton effect.