32 Chemists
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04

Tartaric Acid, Lactic Acid, Louis Pasteur, Jacobus van ’t Hoff, and Joseph Le Bel

Synopsis

Despite Kekulé’s success with the structure of benzene, general recognition that molecules possess a fixed three-dimensional structure did not become widely adopted until the work of van ’t Hoff and Le Bel.

They independently proposed the tetrahedral carbon atom. This model was used to successfully explain the results of Pasteur’s famous experiments separating the enantiomers of tartaric acid. Hermann Kolbe’s nasty ad hominem editorial lambasting van ’t Hoff is an example of the difficulty some scientists have in dealing with change.

Tartaric acid

Structure of (2R,3R)-tartaric acid
(2R,3R)-tartaric acid
L-(+)-tartaric acid — the naturally occurring form.
Structure of (2S,3S)-tartaric acid
(2S,3S)-tartaric acid
D-(−)-tartaric acid — the enantiomer.
Structure of (2R,3S)-tartaric acid
(2R,3S)-tartaric acid
The meso form.
Structure of sodium ammonium tartrate
Sodium ammonium tartrate
The salt Pasteur separated by hand.

Lactic acid

Structure of L-lactic acid
L-lactic acid
The naturally occurring form.
Structure of D-lactic acid
D-lactic acid
The enantiomer.
Structure of 3-hydroxypropanoic acid
3-Hydroxypropanoic acid
Wislicenus’ lactic acid isomer.

Bibliography

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  9. 9Ramberg, P. J. "Johannes Wislicenus, Atomism, and the Philosophy of Chemistry," Bull. Hist. Chem. 1994, 15/16, 45-51. Source
  10. 10Ramberg, P. J.; Somsen, G. J. "The Young J. H. van 't Hoff: The Background to the Publication of his 1874 Pamphlet on the Tetrahedral Carbon Atom, Together with a New English Translation," Annals of Science 2001, 58, 51-74. Source
  11. 11Ramberg, P. J. Chemical Structure, Spatial Arrangement: The Early History of Stereochemistry, 1874-1914; Routledge, 2003.
  12. 12Riddell, F. G.; Robinson, M. J. T. "J. H. van't Hoff and J. A. Le Bel—their historical context," Tetrahedron 1974, 30, 2001-2007. Source
  13. 13Rocke, A. J. Image & Reality: Kekule, Kopp, and the Scientific Imagination; University of Chicago, 2010.
  14. 14van der Spek, T. M. "Selling a Theory: The Role of Molecular Models in J. H. van 't Hoff's Stereochemistry Theory," Annals of Science 2006, 63, 157-177. Source
  15. 15Vantomme, G.; Crassous, J. "Pasteur and chirality: A story of how serendipity favors the prepared minds," Chirality 2021, 33, 597-601. Source
  16. 16Weyer, J. "A Hundred Years of Stereochemistry—The Principal Development Phases in Retrospect," Angew. Chem. Int. Ed. Engl. 1974, 13, 591-598. Source
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