A search for a β effect: the nucleophilicity of the methylene glycolate anion

Shmaryahu Hoz; Dvora Haltovsky

doi:10.1016/S0040-4020(01)88977-8

A search for a β effect: the nucleophilicity of the methylene glycolate anion

Shmaryahu Hoz, Dvora Haltovsky

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

The possible existence of a β-effect (effect of a lone pair of electrons located at a β position of a nucleophile) was investigated by reacting méthyléne glycolate anion with p-nitrophenyl acetate, 2,4-dinitro-fluorobenzene and 2,4-dinitrochlorobenzene in water. For these reactions, no enhanced nucleophile reactivity was found. An upper limit of 2.5 was found for the nucleophilicity n of méthyléne glycolate on the Swain-Scott scale and 6.2±0.2 on Ritchie's N₊ scale.

Original language	English
Pages (from-to)	2049-2052
Number of pages	4
Journal	Tetrahedron
Volume	35
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4020(01)88977-8
State	Published - 1979

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title = "A search for a β effect: the nucleophilicity of the methylene glycolate anion",

abstract = "The possible existence of a β-effect (effect of a lone pair of electrons located at a β position of a nucleophile) was investigated by reacting m{\'e}thyl{\'e}ne glycolate anion with p-nitrophenyl acetate, 2,4-dinitro-fluorobenzene and 2,4-dinitrochlorobenzene in water. For these reactions, no enhanced nucleophile reactivity was found. An upper limit of 2.5 was found for the nucleophilicity n of m{\'e}thyl{\'e}ne glycolate on the Swain-Scott scale and 6.2±0.2 on Ritchie's N+ scale.",

author = "Shmaryahu Hoz and Dvora Haltovsky",

year = "1979",

doi = "10.1016/S0040-4020(01)88977-8",

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AB - The possible existence of a β-effect (effect of a lone pair of electrons located at a β position of a nucleophile) was investigated by reacting méthyléne glycolate anion with p-nitrophenyl acetate, 2,4-dinitro-fluorobenzene and 2,4-dinitrochlorobenzene in water. For these reactions, no enhanced nucleophile reactivity was found. An upper limit of 2.5 was found for the nucleophilicity n of méthyléne glycolate on the Swain-Scott scale and 6.2±0.2 on Ritchie's N+ scale.

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A search for a β effect: the nucleophilicity of the methylene glycolate anion

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