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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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According to Charles Cooley, we base our image on what we think other people see (Cooley 1902). We imagine how we must appear to others, then react to this speculation. We don certain clothes, prepare our hair in a particular manner, wear makeup, use cologne, and the like—all with the notion that our presentation of ourselves is going to affect how others perceive us. We expect a certain reaction, and, if lucky, we get the one we desire and feel good about it. But more than that, Cooley...

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Related Experiment Video

Updated: Jan 22, 2026

A Protocol for Computer-Based Protein Structure and Function Prediction

A Protocol for Computer-Based Protein Structure and Function Prediction

Published on: November 3, 2011

Predictive chirality sensing via Schiff base formation.

Samantha L Pilicer¹, Michele Mancinelli², Andrea Mazzanti²

¹Department of Chemistry, Georgetown University, 37th and O Streets, Washington, DC 20057, USA. cw27@georgetown.edu.

Organic & Biomolecular Chemistry

|June 28, 2019

Summary

New chiral sensors determine absolute configuration and quantify enantiomeric excess (ee) of chiral amines. Sterically crowded designs enable practical CD signal prediction for accurate analysis.

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Area of Science:

Analytical Chemistry
Organic Chemistry
Spectroscopy

Background:

Chiroptical sensors are crucial for analyzing chiral molecules.
Existing sensors often lack the ability to determine absolute configuration and quantify enantiomeric excess (ee).
Development of novel sensors is needed for precise chiral analysis.

Purpose of the Study:

To develop and evaluate stereodynamic N-aryl aminobenzaldehyde sensors for chiral amine analysis.
To enable rational determination of absolute configuration of chiral substrates.
To achieve quantitative enantiomeric excess (ee) analysis of chiral amines.

Main Methods:

Synthesis of stereodynamic N-aryl aminobenzaldehyde sensors.
Chiral amine binding via Schiff base formation.
Circular Dichroism (CD) spectroscopy for signal detection.
Computational analysis to understand sensor behavior and predict CD signals.

Main Results:

The sensors form covalent Schiff bases with chiral amine substrates.
Covalent binding induces conformational bias, generating characteristic CD signals.
Sterically crowded sensor designs facilitate practical CD prediction for absolute configuration determination.
The amplitude of CD signals allows for quantitative ee analysis of nonracemic amine samples.

Conclusions:

Stereodynamic N-aryl aminobenzaldehyde sensors offer a rational approach to determining absolute configuration of chiral amines.
These sensors provide a reliable method for quantitative enantiomeric excess (ee) analysis.
Sterically hindered sensor design is key for accurate and practical chiroptical sensing applications.