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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...

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...

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...

Chirality in Nature

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.

Chirality at Nitrogen, Phosphorus, and Sulfur

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...

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...

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Related Experiment Video

Updated: May 21, 2025

Author Spotlight: Unveiling the Structural and Dynamic Aspects of Glycan Molecular Recognition

Author Spotlight: Unveiling the Structural and Dynamic Aspects of Glycan Molecular Recognition

Published on: May 17, 2024

Molecular Recognition and Chiral Discrimination from NMR and Multi-Scale Simulations.

Tadeu Luiz Gomes Cabral^1,2, João Pedro Brussolo da Silva¹, Claudio Francisco Tormena¹

¹Physical Organic Chemistry Lab, Chemistry Institute, University of Campinas - UNICAMP, Campinas, São Paulo, 13083-970, Brazil.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|March 20, 2025

Summary

This study uses advanced Nuclear Magnetic Resonance (NMR) and computational methods to understand how chiral molecules like Mandelic Acid are distinguished. The research reveals key interactions enabling enantioselective recognition, crucial for pharmaceutical development.

Keywords:

NMR spectroscopy chirality diffusion molecular dynamics quantum chemical calculations

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Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy

Atomic Scale Structural Studies of Macromolecular Assemblies by Solid-state Nuclear Magnetic Resonance Spectroscopy

Published on: September 17, 2017

Area of Science:

Analytical Chemistry
Computational Chemistry
Stereochemistry

Background:

Chiral molecules are vital in pharmaceuticals and agrochemicals, necessitating effective enantiomer separation and identification.
Distinguishing stereoisomers in solution presents a significant analytical hurdle.
Nuclear Magnetic Resonance (NMR) combined with Matrix-Assisted Diffusion-Ordered Spectroscopy (MAD) offers potential for analyzing chiral mixtures, but underlying interactions require deeper understanding.

Purpose of the Study:

To investigate the enantioselective discrimination of Mandelic Acid (MA) enantiomers using (R)-BINOL and (S)-BINOL.
To elucidate the intermolecular interactions responsible for chiral recognition in these systems.
To integrate experimental MAD data with computational modeling for a comprehensive analysis.

Main Methods:

Experimental Matrix-Assisted Diffusion-Ordered Spectroscopy (MAD) studies.
Molecular dynamics (MD) simulations to analyze diffusion coefficients of chiral complexes.
Quantum mechanical (QM) calculations to determine binding preferences and Gibbs free energies.

Main Results:

MD simulations successfully explained differences in diffusion coefficients between heterochiral complexes.
QM calculations confirmed enantioselective binding preferences of BINOL for MA enantiomers, linked to Gibbs free energy differences.
Identified fundamental interactions and structural criteria governing NMR shielding and diffusion trends.

Conclusions:

The integrated experimental and computational approach provides a thorough understanding of chiral recognition mechanisms.
Demonstrated the heterochiral preference of BINOL for Mandelic Acid enantiomers.
Advances chiral analysis techniques and provides a foundation for future stereoisomer identification and recognition studies.