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🤔 OH BOY will Organic Chemistry get even harder for struggling students? In this video, we explain the recent discovery of a one-electron carbon-carbon sigma bond. Although some assume this is completely unprecedented, there is long history of one-electron bonds in general. This video explains the context of this scientific advance, what's really new about it, and the detailed chemistry behind it. https://total-synthesis.com/organic-c... 🧑🎓➡️ Free organic chemistry practice problems / totalsynthesis 🚀 Thanks to all channel supporters!!! / totalsynthesis_official 👉 Follow me on Instagram for updates on random research, mechanism quizzes and interesting news! https://total-synthesis.com 00:00 Chemistry textbooks get even more complicated? 00:29 Basics of covalent bonding and one-electron sigma bonds (Lewis, Pauling) 01:55 Specific examples of one-electron bonds 03:24 How do you create and stabilize a one-electron bond? 05:01 Bond length and its impact on through-bond interaction of orbitals 07:29 Organic synthesis of the strange system and one-electron oxidation 08:44 What does a one-electron bond look like? (ESR, X-Ray) 10:28 Closing and thank you! Key references - sorry quite a few of them were slightly wrong in the video: Direct evidence for a carbon–carbon one-electron σ-bond | Nature 634, 347–351 (2024). https://doi.org/10.1038/s41586-024-07... The Atom and the Molecule | J. Am. Chem. Soc. 1916, 38, 762-785 THE NATURE OF THE CHEMICAL BOND. II. THE ONE-ELECTRON BOND AND THE THREE-ELECTRON BOND | J. Am. Chem. Soc. 1931, 53, 3225 An Intramolecular Boron−Boron One-Electron σ-Bond | J. Am. Chem. Soc. 2000, 122, 37, 9054–9055 Interaction of orbitals through space and through bonds | Acc. Chem. Res. 1971, 4, 1, 1–9 Isolation of a Benzene Valence Isomer with One-Electron Phosphorus-Phosphorus Bonds | Science 1998, 279, 2080 Are One-Electron Bonds Any Different from Standard Two-Electron Covalent Bonds? | Acc. Chem. Res. 2017, 50, 2264 Flexible C−C Bonds: Reversible Expansion, Contraction, Formation, and Scission of Extremely Elongated Single Bonds | Angew. Chem. Int. Ed. 2020, 59, 22252 9,10-Dihydrophenanthrene with Two Spiro(dibenzocycloheptatriene) Units: A Highly Strained Caged Hydrocarbon Exhibiting Reversible Electrochromic Behavior | Molecules 2017, 22(11), 1900 Some recommended books on organic synthesis: Clayden, Greeves, Warren; Organic Chemistry (basic organic chemistry knowledge) Wyatt, Warren; Organic Synthesis: The Disconnection Approach (excellent introduction to retrosynthesis) Kurti, Czako; Strategic Applications of Named Reactions in Organic Synthesis (extensive toolkit of functional group reactions and applications thereof with common conditions) Nicolaou; Classics in Total Synthesis 1-3 (the ultimate total synthesis trilogy) Nicolaou; Molecules That Changed the World (the world's most important molecules and their impact on everyday life) Carreira, Kvaerno; Classics in Stereoselective Synthesis (compilation of the groundbreaking methods of stereoselective synthesis and application to synthesis of stereochemically complex structures)