Elimination reactions of (E)-2,4-dinitrobenzaldehyde O-benzoyloximes promoted by R2NH/R2NH2+ in 70 mol % MeCN(aq). Change of reaction mechanism

Yong Pyun Sang; Rae Cho Bong

doi:10.1021/jo8019412

Elimination reactions of (E)-2,4-dinitrobenzaldehyde O-benzoyloximes promoted by R₂NH/R₂NH₂⁺ in 70 mol % MeCN(aq). Change of reaction mechanism

Yong Pyun Sang, Rae Cho Bong

* Honorary professors

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

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Abstract

(Chemical Equation Presented) Elimination reactions of (E)-2,4-(NO ₂)₂C₆H₃CH=NOC(O)-C₆H ₄X (1) promoted by R₂NH/R₂NH₂ ⁺ in 70 mol % MeCN(aq) have been studied kinetically. The reactions are second-order and exhibit Brönsted β = 0.27-0.32 and |β_lg| = 0.28-0.32. The result can be described by a negligible P_xy interaction coefficient, p_xy = ∂β/ ∂pK_lg = ∂β_lg/∂pK_BH ≈ 0, which describes the interaction between the base catalyst and the leaving group. The negligible p_xy coefficients are consistent with the (E1cb) _irr mechanism.

Original language	English
Pages (from-to)	9451-9453
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	73
Issue number	23
DOIs	https://doi.org/10.1021/jo8019412
Publication status	Published - 2008 Dec 5

ASJC Scopus subject areas

Organic Chemistry

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title = "Elimination reactions of (E)-2,4-dinitrobenzaldehyde O-benzoyloximes promoted by R2NH/R2NH2+ in 70 mol % MeCN(aq). Change of reaction mechanism",

abstract = "(Chemical Equation Presented) Elimination reactions of (E)-2,4-(NO 2)2C6H3CH=NOC(O)-C6H 4X (1) promoted by R2NH/R2NH2 + in 70 mol % MeCN(aq) have been studied kinetically. The reactions are second-order and exhibit Br{\"o}nsted β = 0.27-0.32 and |βlg| = 0.28-0.32. The result can be described by a negligible Pxy interaction coefficient, pxy = ∂β/ ∂pKlg = ∂βlg/∂pKBH ≈ 0, which describes the interaction between the base catalyst and the leaving group. The negligible pxy coefficients are consistent with the (E1cb) irr mechanism.",

author = "Sang, {Yong Pyun} and Bong, {Rae Cho}",

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doi = "10.1021/jo8019412",

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journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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T1 - Elimination reactions of (E)-2,4-dinitrobenzaldehyde O-benzoyloximes promoted by R2NH/R2NH2+ in 70 mol % MeCN(aq). Change of reaction mechanism

AU - Sang, Yong Pyun

AU - Bong, Rae Cho

PY - 2008/12/5

Y1 - 2008/12/5

N2 - (Chemical Equation Presented) Elimination reactions of (E)-2,4-(NO 2)2C6H3CH=NOC(O)-C6H 4X (1) promoted by R2NH/R2NH2 + in 70 mol % MeCN(aq) have been studied kinetically. The reactions are second-order and exhibit Brönsted β = 0.27-0.32 and |βlg| = 0.28-0.32. The result can be described by a negligible Pxy interaction coefficient, pxy = ∂β/ ∂pKlg = ∂βlg/∂pKBH ≈ 0, which describes the interaction between the base catalyst and the leaving group. The negligible pxy coefficients are consistent with the (E1cb) irr mechanism.

AB - (Chemical Equation Presented) Elimination reactions of (E)-2,4-(NO 2)2C6H3CH=NOC(O)-C6H 4X (1) promoted by R2NH/R2NH2 + in 70 mol % MeCN(aq) have been studied kinetically. The reactions are second-order and exhibit Brönsted β = 0.27-0.32 and |βlg| = 0.28-0.32. The result can be described by a negligible Pxy interaction coefficient, pxy = ∂β/ ∂pKlg = ∂βlg/∂pKBH ≈ 0, which describes the interaction between the base catalyst and the leaving group. The negligible pxy coefficients are consistent with the (E1cb) irr mechanism.

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Elimination reactions of (E)-2,4-dinitrobenzaldehyde O-benzoyloximes promoted by R₂NH/R₂NH₂⁺ in 70 mol % MeCN(aq). Change of reaction mechanism

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