Racemates revisited: heterochiral assemblies and the example of dl-thalidomide

Abstract

The existence of racemic compounds, comprised of pairs of opposite enantiomers as discrete molecular entities, has been accepted for over a century. However, their ability to remain as associated dimers when in solution is uncertain, if not generally doubted. In this article, data has been assembled to provide evidence for the presence of intact dimeric heterochiral assemblies in solution and presents DL-thalidomide as a probable example of this phenomenon.

Keywords::

• Racemic compounds
• racemic dimers
• enantiomeric associates

Acknowledgement

The authors are grateful to Prof. John Lindon and Prof. Jeremy Nicholson for their constructive review of the manuscript and their comments.

Declaration of interest

The authors report no conflicts of interest. The authors alone are responsible for the content and writing of the article.