Determination of absolute configuration—An overview related to this Special Issue

Abstract

Rapid progress in asymmetric synthesis stimulated a further development of methods and techniques for the determination of absolute configuration of chiral molecules. In recent years the direct methods, i.e. X-ray diffraction analysis, circular dichroism (vibrational and electronic), Raman optical activity, optical rotation measurements, as well as indirect methods for relative configuration assignment with the use of NMR spectroscopy or enzymatic transformations, are receiving increasing attention not only by specialists in the field but also by synthetic and structural chemists alike. This paper provides a short overview of the methods currently used, as well as references to contributions collected in this Thematic Issue of Chirality.

Probing chiral solute-water hydrogen bonding networks by chirality transfer effects: A vibrational circular dichroism study of glycidol in water

“…[11][12][13] VCD spectroscopy, in combination with the DFT calculations, has emerged as a very promising tool for absolute configuration determinations of chiral organic compounds. [14][15][16][17][18] More recently, it has been recognized that VCD spectra are highly sensitive to specific hydrogen bonding environments. Such hydrogen bonding interactions can cause not only the shapes but also the signs of the related VCD bands to alter.…”

Complementarity of electronic and vibrational circular dichroism based on stereochemical studies of vic-diols

“…In the light of the above, the combined application of both these methods may bring detailed stereochemical information about molecules studied and substantially increase the credibility of unequivocal configurational assignment [10,11]. Such an approach is particularly useful for monitoring and characterizing even the smallest changes of molecular skeleton in solution and solid phase.…”

Synthesis of Cryptochiral (R,R)‐2,3‐Dideuterooxirane as Stereochemical Reference Compound and Chemical Correlation with D‐(+)‐Glyceraldehyde

“…Van't Hoff and Le Bel realized that molecular handedness in organic compounds can be explained by the tetrahedral structure of tetrasubsituted sp 3 ‐hybridized carbon atoms, which form stereogenic centers. [3,4] However, the determination of absolute configurations is a nontrivial problem and can be a challenging task . The knowledge of the absolute configuration is of great importance, e.g., in the lock‐and‐key relationship or structure‐specific targeting in drug development .…”