prototropyn.
/prəʊˈtɒtrəpi/, U.S. /proʊˈtɑtrəpi/ Chemistry.
Tautomerism in which the forms differ only in the position of a proton; migration of a proton from one part of a molecule to another.
ΘΚΠ
the world > matter > chemistry > isomerism > [noun] > structural isomerism > tautomerism > types of
prototropy1923
anionotropy1928
mesomerism1928
1923 T. M. Lowry in Jrnl. Chem. Soc. 123 828 Prototropy, or the reversible change of protomers, which differ from one another in the position of a proton or hydrogen nucleus.
1964 N. G. Clark Mod. Org. Chem. xv. 296 The behaviour of ethyl acetoacetate is another example of the phenomenon of tautomerism, in particular of prototropy.
2000 J. L. McLain et al. in B. Meunier Biomimetic Oxidations iii. 105 The oxo-aqua exchange rate was about 103 s−1 for the coordinated water, a process which occurred by prototropy.
Derivatives
protoˈtropic adj. of, relating to, or exhibiting prototropy.
ΘΚΠ
the world > matter > chemistry > isomerism > [adjective] > of or relating to structural isomerism > of or relating to tautomerism > of specific types of
prototropic1925
1925 Jrnl. Chem. Soc. 127 1382 Prototropic changes, which involve only the migration of a proton, are catalysed both by acids and by alkalis, like the hydrolysis of an ester.
1953 C. K. Ingold Struct. & Mech. Org. Chem. x. 579 2-hydroxypyridine, or α-pyridone, as it is usually named after its prototropic tautomer.
1981 P. Sykes Guidebk. to Mechanism in Org. Chem. (ed. 5) x. 272 Prototropic interconversions..lend themselves particularly well to investigation by deuterium labelling.
This entry has been updated (OED Third Edition, September 2007; most recently modified version published online March 2022).
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n.1923