Temperature dependence of the alpha-ester rearrangement reaction

Geoffrey S. Tyndall; Andre S. Pimentel; J. J. Orlando

doi:10.1021/jp048537c

Temperature dependence of the alpha-ester rearrangement reaction

Geoffrey S. Tyndall, Andre S. Pimentel, J. J. Orlando

Experimental Science Section

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21 Scopus citations

Abstract

Measurements have been made of the oxidation products of methyl formate and methyl acetate as a function of temperature (253-324 K). Both processes show the occurrence of the α-ester rearrangement channel RC(O)OCH ₂O→ RC(O)OH + HCO, which has an activation energy of ∼10 kcal mol ^-1. Reaction of hydroxyl radicals with methyl formate occurs with roughly equal efficiency at both of the carbon atoms, while OH-reaction with methyl acetate leads to 30-40% attack at the acetate group.

Original language	English
Pages (from-to)	6850-6856
Number of pages	7
Journal	Journal of Physical Chemistry A
Volume	108
Issue number	33
DOIs	https://doi.org/10.1021/jp048537c
State	Published - Aug 19 2004

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title = "Temperature dependence of the alpha-ester rearrangement reaction",

abstract = "Measurements have been made of the oxidation products of methyl formate and methyl acetate as a function of temperature (253-324 K). Both processes show the occurrence of the α-ester rearrangement channel RC(O)OCH 2O→ RC(O)OH + HCO, which has an activation energy of ∼10 kcal mol -1. Reaction of hydroxyl radicals with methyl formate occurs with roughly equal efficiency at both of the carbon atoms, while OH-reaction with methyl acetate leads to 30-40\% attack at the acetate group.",

author = "Tyndall, \{Geoffrey S.\} and Pimentel, \{Andre S.\} and Orlando, \{J. J.\}",

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journal = "Journal of Physical Chemistry A",

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T1 - Temperature dependence of the alpha-ester rearrangement reaction

AU - Tyndall, Geoffrey S.

AU - Pimentel, Andre S.

AU - Orlando, J. J.

PY - 2004/8/19

Y1 - 2004/8/19

N2 - Measurements have been made of the oxidation products of methyl formate and methyl acetate as a function of temperature (253-324 K). Both processes show the occurrence of the α-ester rearrangement channel RC(O)OCH 2O→ RC(O)OH + HCO, which has an activation energy of ∼10 kcal mol -1. Reaction of hydroxyl radicals with methyl formate occurs with roughly equal efficiency at both of the carbon atoms, while OH-reaction with methyl acetate leads to 30-40% attack at the acetate group.

AB - Measurements have been made of the oxidation products of methyl formate and methyl acetate as a function of temperature (253-324 K). Both processes show the occurrence of the α-ester rearrangement channel RC(O)OCH 2O→ RC(O)OH + HCO, which has an activation energy of ∼10 kcal mol -1. Reaction of hydroxyl radicals with methyl formate occurs with roughly equal efficiency at both of the carbon atoms, while OH-reaction with methyl acetate leads to 30-40% attack at the acetate group.

UR - https://www.scopus.com/pages/publications/4344669507

U2 - 10.1021/jp048537c

DO - 10.1021/jp048537c

M3 - Article

AN - SCOPUS:4344669507

SN - 1089-5639

VL - 108

SP - 6850

EP - 6856

JO - Journal of Physical Chemistry A

JF - Journal of Physical Chemistry A

IS - 33

ER -

Temperature dependence of the alpha-ester rearrangement reaction

Abstract

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