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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Letter Article

A Rationale for the Ortho Effect in Electrophilic Aromatic Substitutions

Author(s): Timothy Eckert*, Grace Harmeyer, Steven Legate and Steven Mathe

Volume 17, Issue 9, 2020

Page: [655 - 658] Pages: 4

DOI: 10.2174/1570178617666200207103755

Price: $65

Abstract

The ortho effect arises in certain electrophilic aromatic substitutions when a meta director is meta to an ortho/para director. Among the three expected isomer products, only the two isomers ortho to the meta director are produced normally. To find an explanation for the ortho effect, nitrations of two properly substituted benzenes were explored. Evidence supported an explanation based on resonance involving the meta director.

Keywords: Electrophilic aromatic substitutions, ortho effect, resonance, nitration, directing groups, meta director.

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Graphical Abstract
[1]
Smith, M.B.; March, J. March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure; Wiley: Hoboken, 2013, p. 583.
[2]
Hammond, G.S.; Hawthorne, M.F. Newman, M.S. Steric Effects in Organic Chemistry; Wiley: New York, 1956, p. 181.
[3]
Ingold, C.K. Aromatic Substitution. Structure and Mechanism in Organic Chemistry, 2nd ed; Cornell University Press: Ithaca, 1969.
[4]
Holleman, A.F. Die direkte Einführung von Substituenten in den Benzolkern, 1st ed; Verlag: Veit, Leipzig 1910.
[5]
McDaniel, D.H.; Brown, H.C. J. Org. Chem., 1958, 23, 420.

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