The gas-phase ion chemistry of an enol/aldehyde pair: 2,2-dimesitylethenol and 2,2-dimesitylethanal

Irene Rabin; Silvio E. Biali; Zvi Rappoport; Chava Lifshitz

doi:10.1016/0168-1176(86)87005-7

The gas-phase ion chemistry of an enol/aldehyde pair: 2,2-dimesitylethenol and 2,2-dimesitylethanal

Irene Rabin^*, Silvio E. Biali, Zvi Rappoport, Chava Lifshitz

^*Corresponding author for this work

Institute of Chemistry

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

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Abstract

The gas-phase ion chemistry of 2,2-dimesitylethenol and 2,2-dimesitylethanal was studied by deuterium labelling, by MS/MS techniques involving MIKES, CAD-MIKES and linked scans, by measurements of kinetic energy releases in unimolecular decompositions, and by ionization and appearance energy determinations. The results are discussed in terms of keto-enol tautomerization and specific rearrangements of crowded enols such as reciprocal methyl/hydrogen transfer reactions. Dish-topped metastable peak shapes are obtained for 1,3 hydrogen atom shifts from oxygen to carbon followed by CC cleavages, when the hydroxyl bearing carbon atom is bound to hydrogen.

Original language	English
Pages (from-to)	301-320
Number of pages	20
Journal	International Journal of Mass Spectrometry and Ion Processes
Volume	70
Issue number	3
DOIs	https://doi.org/10.1016/0168-1176(86)87005-7
State	Published - 15 Jul 1986

Bibliographical note

Funding Information:
This research was supported by the United States-Israel Binational Science Foundation (BSF), Israel. The ZAB-2F was purchased through a grant from the Committee for Higher Education, Israel. We are indebted to Mrs. T. Peres for her help in operating the ZAB.

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title = "The gas-phase ion chemistry of an enol/aldehyde pair: 2,2-dimesitylethenol and 2,2-dimesitylethanal",

abstract = "The gas-phase ion chemistry of 2,2-dimesitylethenol and 2,2-dimesitylethanal was studied by deuterium labelling, by MS/MS techniques involving MIKES, CAD-MIKES and linked scans, by measurements of kinetic energy releases in unimolecular decompositions, and by ionization and appearance energy determinations. The results are discussed in terms of keto-enol tautomerization and specific rearrangements of crowded enols such as reciprocal methyl/hydrogen transfer reactions. Dish-topped metastable peak shapes are obtained for 1,3 hydrogen atom shifts from oxygen to carbon followed by CC cleavages, when the hydroxyl bearing carbon atom is bound to hydrogen.",

author = "Irene Rabin and Biali, {Silvio E.} and Zvi Rappoport and Chava Lifshitz",

note = "Funding Information: This research was supported by the United States-Israel Binational Science Foundation (BSF), Israel. The ZAB-2F was purchased through a grant from the Committee for Higher Education, Israel. We are indebted to Mrs. T. Peres for her help in operating the ZAB.",

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AU - Rappoport, Zvi

AU - Lifshitz, Chava

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AB - The gas-phase ion chemistry of 2,2-dimesitylethenol and 2,2-dimesitylethanal was studied by deuterium labelling, by MS/MS techniques involving MIKES, CAD-MIKES and linked scans, by measurements of kinetic energy releases in unimolecular decompositions, and by ionization and appearance energy determinations. The results are discussed in terms of keto-enol tautomerization and specific rearrangements of crowded enols such as reciprocal methyl/hydrogen transfer reactions. Dish-topped metastable peak shapes are obtained for 1,3 hydrogen atom shifts from oxygen to carbon followed by CC cleavages, when the hydroxyl bearing carbon atom is bound to hydrogen.

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The gas-phase ion chemistry of an enol/aldehyde pair: 2,2-dimesitylethenol and 2,2-dimesitylethanal

Abstract

Bibliographical note

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