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Properties of Enantiomers and Optical Activity

Properties of Enantiomers and Optical Activity

It is essential to understand the difference between chiral and achiral interactions and the implications thereof in optical activity and their applications. Just as our feet, which are chiral, interact uniquely with chiral objects, such as a pair of shoes, but identically with achiral socks, enantiomers of a molecule exhibit different properties only when they interact with other chiral media. An example of a significant implication from this facet is the phenomenon known as optical activity,...

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.
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Molecules with Multiple Chiral Centers

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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...

Chirality in Nature

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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.

Fischer Projections

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Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines.

Prochirality

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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

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Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

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First Principles Simulations of Optical Rotation of Chiral Molecular Crystals.

Emmanuel Forson¹, Taylor Parsons¹, Marco Caricato¹

¹Department of Chemistry, University of Kansas, Lawrence, Kansas, USA.

|August 5, 2024

Summary

Simulations of optical rotation (OR) in crystals show promise, matching experimental data for some compounds. Discrepancies in others suggest revisiting experiments and improving hydrogen atom positioning for accurate OR predictions.

Keywords:

chiral crystals density functional theory optical rotation periodic boundary conditions

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Area of Science:

Computational Chemistry
Solid-State Physics
Crystallography

Background:

Optical rotation (OR) is a crucial chiroptical property for characterizing chiral molecules and materials.
Accurate theoretical prediction of OR in molecular crystals is challenging due to complex intermolecular interactions and structural details.

Purpose of the Study:

To simulate and evaluate the optical rotation of five molecular crystals using density functional theory with periodic boundary conditions (DFT-PBC).
To compare simulation results with experimental data and identify factors influencing prediction accuracy.

Main Methods:

Density functional theory calculations with periodic boundary conditions (DFT-PBC) were employed.
Simulations were performed for tartaric acid, benzil, pentaerythritol, aspartic acid, and glutamic acid crystals.
Hydrogen atom positions were optimized in some calculations, deviating from fixed experimental X-ray data.

Main Results:

Semi-quantitative agreement between calculated and experimental OR was achieved for tartaric acid, benzil, and pentaerythritol.
Calculated OR for aspartic acid and glutamic acid was qualitatively consistent but two orders of magnitude smaller than experimental values.
Optimizing hydrogen atom positions improved simulation accuracy compared to using fixed experimental X-ray data.

Conclusions:

DFT-PBC simulations offer a viable approach for studying OR in molecular crystals, highlighting the importance of intermolecular interactions.
Discrepancies in certain crystals suggest potential issues with experimental data, particularly hydrogen atom placement, warranting experimental re-evaluation.
Further development of theoretical methods is needed to fully capture the nuances of OR in crystalline materials.