A positive deviation
of an α-nucleophile (a nucleophile bearing an unshared pair of electrons on an atom
adjacent to the nucleophilic site) from a Brønsted-type plot of
constructed for a series of related normal nucleophiles. More generally, it is the
influence of the atom bearing a lone pair of electrons on the reactivity at the adjacent
The use of the term has been extended to include the effect of any substituent on
an adjacent reactive centre, for example in the case of the 'α-silicon effect'.
PAC, 1994, 66, 1077
(Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994))
on page 1088
IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by
A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997).
XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic,
J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. https://doi.org/10.1351/goldbook