https://doi.org/10.15255/KUI.2007.026
Published: Kem. Ind. 56 (5) (2007) 275–292
Paper reference number: KUI-26/2007
Paper type: Review
Download paper:  PDF

Chirality – The forthcoming 160th Anniversary of Pasteur’s Discovery

K. Molčanov and B. Kojić-Prodić

Abstract

The presented review on chirality is dedicated to the centennial birth anniversary of Nobel laureate Vladimir Prelog and 160 years of Pasteur’s discovery of chirality on tartrates. Chirality has been recognized in nature by artists and architects, who have used it for decorations and basic constructions, as shown in the Introduction. The progress of science through history has enabled the gathering of knowledge on chirality and its many ways of application. The key historical discoveries about the rotation of polarized light as a consequence of molecular chirality and findings of Pasteur and Lord Kelvin are described. Chirality can be found in physics of elementary particles and in many fields of chemistry: analytical and organic chemistry, chemistry of natural compounds, medicinal and pharmaceutical chemistry, biochemistry and biotechnology, and molecular biology. The development of knowledge about chirality and its physical background are briefly described. Definitions for geometrical, topological, and conformational chirality are given accompanied by numerous examples of molecules exhibiting such features. The relations between symmetry and chirality in crystallography are exposed. X-ray crystallography is a method of choice for unambiguous determination of molecular architecture, including the absolute configuration of the molecule using Bijvoet’s approach. Two methods of determination of absolute configuration by X-ray diffraction and circular dichroism are briefly discussed. To mark two significant jubilees, the essay is dedicated to the role of chirality in stereochemistry. Stereochemistry is not a branch of chemistry but rather a view at chemistry, as considered by E. L. Eliel; this approach is respected in the essay presented. This very approach leads to various aspects of chirality and brings to the consistency of many definitions. The future will bring us knowledge on the role of chirality in communications among molecules, which guide our life processes. The synthesis of various dynamically chiral supramolecules from achiral molecules and preparations of conjugated homochiral polymers will offer new types of biosensors, artificial enzymes and some sophisticated materials. The research of isotopic chirality by quantum-chemical methods reveals some parity-violating effects and shed more light on the physical bases of molecular chirality.

This work is licensed under a Creative Commons Attribution 4.0 International License

Keywords

geometric chirality, topological chirality, symmetry, achirality, absolute configuration, absolute conformation, anomalous dispersion of X-rays, Bijvoet pairs, circular dichroism