This contributed volume is based on presentations made at the 2024 Symposium on the sesquicentennial of the independent proposals of the tetrahedral carbon by van 't Hoff and Le Bel (1874), presented to the Division of the History of Chemistry of the American Chemical Society in March 2024. In 1874, the Dutch chemist, Jacobus Henricus van 't Hoff (1852-1911), and the French chemist, Joseph-Achille Le Bel (1847-1930), independently proposed that the phenomenon of optical activity could be rationalized on the basis of non-superimposable mirror image moleculesin particular, the tetrahedral carbon atom. The book features chapters dedicated to the life and work of Le Bel and the history of stereochemistry. The expansion of the van 't Hoff-Le Bel theory to elements beyond carbon, such as metals and chiral centers based on sulfur and selenium, is also explored. Additionally, the book discusses the visualization of organic molecules in three dimensions through molecular models, the limits of bonding and stereochemistry in organic molecules, and the role of crystallography in stereochemistry development. Specific topics include hydrocarbons with severely distorted geometry, the quantum chemical revolution, the effects of substituents on tetrahedral carbons, the Walden inversion, and the Fischer elucidation of monosaccharide configurations. A chapter by Kahr and Rossi includes the only English translation of the undergraduate thesis of the world-renowned author Primo Levi, a Jewish, Italian-born chemist and Holocaust survivor, and provides historical and scientific context. The book also examines the public celebration of stereochemistry through postage stamps. This title offers a comprehensive overview of the evolution and significance of stereochemistry in both chemistry and scientific thought, serving as a valuable resource for students and researchers interested in history of chemistry topics.

Presents the evolution and significance of stereochemistry Provides a comprehensive coverage of the topic Includes contributions from leading experts in this field

Autorentext

Arthur Greenberg, Professor Emeritus at the University of New Hampshire, is an organic chemist interested in unusual (high-energy, distorted) molecules. Prior to joining UNH and serving as dean of Engineering and Physical Sciences (2000-2005), he was the chemistry department chair at the University of North Carolina at Charlotte (1994-2000) and prior to that director of the graduate program in environmental sciences at Rutgers University (1989-1994). He earned his Ph.D. from Princeton University in 1971. He is a Fellow of the ACS and a Fellow of the HIST Division. Most recently he served as Chair of the HIST Division in 2023 and 2024.

He has published more than 140 refereed articles and book chapters, authored four books, and co-authored one book. He is the founding co-editor of the journal Structural Chemistry. Professor Greenberg's most recent book, From Alchemy to Chemistry in Picture and Story, was published by John Wiley and Sons.

David E. Lewis, Professor Emeritus at the University of Wisconsin-Eau Claire, is an organic chemist whose interests are in organic synthesis and the history of organic chemistry in Russia. He was educated (B.Sc., Ph.D., D.Sc.) at the University of Adelaide, South Australia. He built his independent career in the U.S., retiring in 2022. He is the author of over 110 refereed journal articles and book chapters, 12 open-access columns in Synform, and 7 books; he served as the English-language editor of the English translation of a compendium published in Russia: Beloglazkina, E.; Beletskaya, I.; Lewis, D.; Nenajdenko, V. (Eds.) History of Organic Chemistry at Russian Universities. From Origins to the Present Day; NGB Publishing House: Moscow, 2022. His most recent books are The Wolff-Kishner Reduction and Related Reactions, Organic Name Reactions. Biographies, Discovery and Development and Addition, Elimination and Substitution: Markovnikov, Hofmann, Zaitsev and Walden. Discovery and Development, both published by Elsevier. He is the American Associate Editor for Synthetic Communications.

He is a Fellow of the Royal Society of Chemistry and of the Royal Australian Chemical Institute, a HIST Fellow, and former Chair of HIST. He received the 2018 Joseph B. Lambert HIST Award for Outstanding Achievement in the History of Chemistry and the 2019 Markovnikov Medal for Outstanding Achievement in Organic Chemistry (presented by Lomonosov Moscow State University, Russia).

Inhalt

Part I: Introductory Chapters.- Stamps are Planar, Carbon is Not: A Philatelic History of Chemistry.- The History of Stereochemistry: Progress and Prospects.- Part II: Stereochemical Pioneers.- Joseph-Achille Le Bel: Polymath Extraordinary.- Alfred Werner: Coordination Theory and the Stereochemistry of Metal Complexes.- Studies of Chiral Centers Other than Carbon. William Jackson Pope and Kurt Mislow: Pioneers of Stereochemistry.- Missed It by That Much! How Butlerov Almost Proposed the Tetrahedral Carbon.- Rene Just Hauy and the Contribution of Crystallography to 3-Dimensional Chemistry.- Part III: Using Stereochemistry to Study Reactions and Structure.- L'Inversione di Walden: The Undergraduate Thesis of Primo Levi, Chemist and Writer.- ''How Sweet It Is! Emil Fischer's Stereochemical Studies of Glucose.- Part IV: Exploring the Limits of Organic Structure.- Historical Evolution, Stereochemistry, and Structural Limitations for the C=C Bond.- Exploring Variation in Bonding and Structure for Tetrahedral Carbon: [1.1.1]Propellane and Inverted Carbons.- Expansion of the Definition of Stereochemistry to Include Quantum Chemistry. When 'Funny' is Fun but not Funny.- Although sp3 Hybridization is Not Found for The Carbon in Methane Nor in Isoelectronically Related Species. The Concept of Hybridization is Still Useful and Powerful.