A readily observed base-catalyzed isotopic exchange in a 2,4-dinitroalkyl benzene

Nick Backstrom; C. I F Watt

doi:10.1016/j.tetlet.2009.02.002

A readily observed base-catalyzed isotopic exchange in a 2,4-dinitroalkyl benzene

Nick Backstrom
, C. I F Watt

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

Abstract

The behaviour of solutions of the sodium salt of 4-(2,4-dinitrophenyl)pentanoic acid in D2O is readily monitored by 1H NMR spectroscopy. In the presence of excess NaOD, these show exchange of hydrogen at the 3-position of the benzene ring with kOD = 1.23(0.03) × 10-4 M-1 s-1 at 25 °C. Rates of exchange using solutions with triethylamine buffers show no dependence on buffer concentration and an estimate of the acid dissociation constant, pKa ≈ 29.3, of the dinitrobenzene is made. Under the conditions, there is no detectable exchange at the benzylic position. © 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3234-3236
Number of pages	2
Journal	Tetrahedron Letters
Volume	50
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2009.02.002
Publication status	Published - 1 Jul 2009

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title = "A readily observed base-catalyzed isotopic exchange in a 2,4-dinitroalkyl benzene",

abstract = "The behaviour of solutions of the sodium salt of 4-(2,4-dinitrophenyl)pentanoic acid in D2O is readily monitored by 1H NMR spectroscopy. In the presence of excess NaOD, these show exchange of hydrogen at the 3-position of the benzene ring with kOD = 1.23(0.03) × 10-4 M-1 s-1 at 25 °C. Rates of exchange using solutions with triethylamine buffers show no dependence on buffer concentration and an estimate of the acid dissociation constant, pKa ≈ 29.3, of the dinitrobenzene is made. Under the conditions, there is no detectable exchange at the benzylic position. {\textcopyright} 2009 Elsevier Ltd. All rights reserved.",

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year = "2009",

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doi = "10.1016/j.tetlet.2009.02.002",

language = "English",

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T1 - A readily observed base-catalyzed isotopic exchange in a 2,4-dinitroalkyl benzene

AU - Backstrom, Nick

AU - Watt, C. I F

PY - 2009/7/1

Y1 - 2009/7/1

N2 - The behaviour of solutions of the sodium salt of 4-(2,4-dinitrophenyl)pentanoic acid in D2O is readily monitored by 1H NMR spectroscopy. In the presence of excess NaOD, these show exchange of hydrogen at the 3-position of the benzene ring with kOD = 1.23(0.03) × 10-4 M-1 s-1 at 25 °C. Rates of exchange using solutions with triethylamine buffers show no dependence on buffer concentration and an estimate of the acid dissociation constant, pKa ≈ 29.3, of the dinitrobenzene is made. Under the conditions, there is no detectable exchange at the benzylic position. © 2009 Elsevier Ltd. All rights reserved.

AB - The behaviour of solutions of the sodium salt of 4-(2,4-dinitrophenyl)pentanoic acid in D2O is readily monitored by 1H NMR spectroscopy. In the presence of excess NaOD, these show exchange of hydrogen at the 3-position of the benzene ring with kOD = 1.23(0.03) × 10-4 M-1 s-1 at 25 °C. Rates of exchange using solutions with triethylamine buffers show no dependence on buffer concentration and an estimate of the acid dissociation constant, pKa ≈ 29.3, of the dinitrobenzene is made. Under the conditions, there is no detectable exchange at the benzylic position. © 2009 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2009.02.002

DO - 10.1016/j.tetlet.2009.02.002

M3 - Article

SN - 1873-3581

VL - 50

SP - 3234

EP - 3236

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

A readily observed base-catalyzed isotopic exchange in a 2,4-dinitroalkyl benzene

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