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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,...

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...

Chair Conformation of Cyclohexane

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...

Conformations of Cyclohexane

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...

Naming Enantiomers

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...

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Related Experiment Video

Updated: Jun 22, 2025

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

High Rotational Barrier Atropisomers.

Michael Fragkiadakis¹, Maria Thomaidi¹, Taxiarchis Stergiannakos¹

¹Department of Chemistry, University of Crete, Voutes, Heraklion, 70013, Greece.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|July 4, 2024

Summary

Researchers developed a new method using multicomponent reaction (MCR) chemistry for synthesizing complex atropisomers with high rotational barriers. This advance expands synthetic strategies for these valuable molecules in drug discovery and organic synthesis.

Keywords:

Density functional calculations Multicomponent reactions Noncovalent interactions Pi interactions

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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Published on: February 7, 2019

Area of Science:

Organic Chemistry
Medicinal Chemistry
Computational Chemistry

Background:

Atropisomers are crucial in organic synthesis and drug discovery.
Limited synthetic methods exist for accessing complex atropisomers.

Purpose of the Study:

To develop a novel synthetic strategy for atropisomers using multicomponent reaction (MCR) chemistry.
To investigate the structure-property relationships of newly synthesized atropisomers.

Main Methods:

De novo synthesis of atropisomers via MCR chemistry.
Crystallography, Nuclear Magnetic Resonance (NMR) spectroscopy, and Density Functional Theory (DFT) calculations for molecular analysis.
Monitoring of various intermolecular interactions (π-π, CH-π, heteroatom-π, CD-π).

Main Results:

Successful de novo synthesis of a class of atropisomers with high rotational barriers.
Simultaneous insertion of multiple chiral elements into the atropisomeric structures.
Detailed characterization of molecular interactions and electronic properties.

Conclusions:

MCR chemistry provides an effective strategy for synthesizing complex atropisomers.
The studied atropisomers exhibit unique structural and interaction properties.
Findings support applications in atroposelective synthesis and drug discovery.