Prototropic Equilibrium of Imines. N-Benzylidene Benzylamines

Peter A.S. Smith; Chi Van Dang

doi:10.1021/jo00873a027

Prototropic Equilibrium of Imines. N-Benzylidene Benzylamines

Peter A.S. Smith, Chi Van Dang

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

39 Scopus citations

Abstract

The 1,3-prototropic shift of imines, exemplified in isomerization of unsymmetrically substituted N-benzylidene benzylamines, has been reexamined. Equilibrium constants for para-monosubstituted systems were determined by NMR methods; the constants do not show the anomalies reported in older work, and are adequately correlated by the Hammett equation (ρ = 0.94).

Original language	English (US)
Pages (from-to)	2013-2015
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	41
Issue number	11
DOIs	https://doi.org/10.1021/jo00873a027
State	Published - May 1 1976
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Prototropic Equilibrium of Imines. N-Benzylidene Benzylamines",

abstract = "The 1,3-prototropic shift of imines, exemplified in isomerization of unsymmetrically substituted N-benzylidene benzylamines, has been reexamined. Equilibrium constants for para-monosubstituted systems were determined by NMR methods; the constants do not show the anomalies reported in older work, and are adequately correlated by the Hammett equation (ρ = 0.94).",

author = "Smith, {Peter A.S.} and {Van Dang}, Chi",

year = "1976",

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N2 - The 1,3-prototropic shift of imines, exemplified in isomerization of unsymmetrically substituted N-benzylidene benzylamines, has been reexamined. Equilibrium constants for para-monosubstituted systems were determined by NMR methods; the constants do not show the anomalies reported in older work, and are adequately correlated by the Hammett equation (ρ = 0.94).

AB - The 1,3-prototropic shift of imines, exemplified in isomerization of unsymmetrically substituted N-benzylidene benzylamines, has been reexamined. Equilibrium constants for para-monosubstituted systems were determined by NMR methods; the constants do not show the anomalies reported in older work, and are adequately correlated by the Hammett equation (ρ = 0.94).

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M3 - Article

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JO - Journal of Organic Chemistry

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Prototropic Equilibrium of Imines. N-Benzylidene Benzylamines

Abstract

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