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Molecules with Multiple Chiral Centers

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...

SN2 Reaction: Stereochemistry

S_N2 Reaction: Stereochemistry

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.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...

Prochirality

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...

SN1 Reaction: Stereochemistry

S_N1 Reaction: Stereochemistry

This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...

Chirality

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...

Stereoisomerism of Cyclic Compounds

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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Related Experiment Video

Updated: Jul 22, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Unimolecular Chiral Stepping Inversion Machine.

Yonghui Sun¹, Lijuan Liu¹, Linnan Jiang¹

¹College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China.

Journal of the American Chemical Society

|July 24, 2023

Summary

This study presents a novel unimolecular chiral stepping inversion molecular machine (SIMM) that achieves reversible chiral inversion using redox stimuli. This molecular machine offers a new pathway for developing advanced stimulus-responsive chiral systems.

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Area of Science:

Molecular machines
Supramolecular chemistry
Chirality

Background:

Intelligent molecular machines responsive to light, electricity, and temperature are of significant interest.
Stimulus-responsive molecular machines are crucial for advancements in chemistry, materials science, and biology.

Purpose of the Study:

To construct and investigate a unimolecular chiral stepping inversion molecular machine (SIMM).
To demonstrate redox-triggered chiral inversion and reversible switching of CD signaling.

Main Methods:

Synthesis of a SIMM via coupling dibromo pillar[5]arene and a tetrathiafulvalene (TTF) derivative.
Electrochemical experiments to study redox properties.
Circular dichroism (CD) spectroscopy to monitor chiral switching.

Main Results:

The SIMM exhibits chiral stepping inversion triggered by a two-electron redox potential.
Redox processes induce reversible switching of SIMM's CD signal.
Chiral inversion was achieved and reversed using chemical oxidants and reducing agents.

Conclusions:

This work demonstrates unimolecular chiral stepping inversion in response to redox stimuli.
The developed SIMM provides a new platform for stimulus-responsive chirality.
This research opens new avenues for designing advanced molecular machines.