Lability

Lability is the opposite of stability. Something is more labile if it is easier to move or change. The term is normally used in science, especially biology and chemistry.

Chemistry

In chemistry, "labile" can mean both an unstable chemical or reaction intermediate, or a stable but reactive chemical.^[1] It is also used to describe atoms or parts of a molecule that can be removed from molecules by chemical reactions,^[2] especially hydrogen atoms.^[3]^[4]

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Sources

↑ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "labile". doi:10.1351/goldbook.L03432
↑ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "acid-labile sulfur". doi:10.1351/goldbook.AT06794
↑ Siskos, Michael; Choudhary, M.; Gerothanassis, Ioannis (2017). "Hydrogen Atomic Positions of O–H···O Hydrogen Bonds in Solution and in the Solid State: The Synergy of Quantum Chemical Calculations with 1H-NMR Chemical Shifts and X-ray Diffraction Methods". Molecules. 22 (3): 415. doi:10.3390/molecules22030415. PMC 6155303. PMID 28272366.
↑ Novakovic, Mihajlo; Battistel, Marcos D.; Azurmendi, Hugo F.; Concilio, Maria-Grazia; Freedberg, Darón I.; Frydman, Lucio (2021). "The Incorporation of Labile Protons into Multidimensional NMR Analyses: Glycan Structures Revisited". Journal of the American Chemical Society. 143 (23): 8935–8948. Bibcode:2021JAChS.143.8935N. doi:10.1021/jacs.1c04512. PMID 34085814.

[1] IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "labile". doi:10.1351/goldbook.L03432

[2] IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "acid-labile sulfur". doi:10.1351/goldbook.AT06794

[3] Siskos, Michael; Choudhary, M.; Gerothanassis, Ioannis (2017). "Hydrogen Atomic Positions of O–H···O Hydrogen Bonds in Solution and in the Solid State: The Synergy of Quantum Chemical Calculations with 1H-NMR Chemical Shifts and X-ray Diffraction Methods". Molecules. 22 (3): 415. doi:10.3390/molecules22030415. PMC 6155303. PMID 28272366.

[4] Novakovic, Mihajlo; Battistel, Marcos D.; Azurmendi, Hugo F.; Concilio, Maria-Grazia; Freedberg, Darón I.; Frydman, Lucio (2021). "The Incorporation of Labile Protons into Multidimensional NMR Analyses: Glycan Structures Revisited". Journal of the American Chemical Society. 143 (23): 8935–8948. Bibcode:2021JAChS.143.8935N. doi:10.1021/jacs.1c04512. PMID 34085814.

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