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α-effect

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 log k nuc vs. p K a 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 site.
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'.
Source:
PAC, 1994, 66, 1077 (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1088
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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. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.A00006.
Original PDF version: http://www.iupac.org/goldbook/A00006.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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