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  • Synchrotron photoionization measurements of OH-initiated cyclohexene oxidation: ring-preserving products in OH + cyclohexene and hydroxycyclohexyl + O2 reactions.

Synchrotron photoionization measurements of OH-initiated cyclohexene oxidation: ring-preserving products in OH + cyclohexene and hydroxycyclohexyl + O2 reactions.

The journal of physical chemistry. A (2012-05-29)
Amelia W Ray, Craig A Taatjes, Oliver Welz, David L Osborn, Giovanni Meloni
ABSTRACT

Earlier synchrotron photoionization mass spectrometry experiments suggested a prominent ring-opening channel in the OH-initiated oxidation of cyclohexene, based on comparison of product photoionization spectra with calculated spectra of possible isomers. The present work re-examines the OH + cyclohexene reaction, measuring the isomeric products of OH-initiated oxidation of partially and fully deuterated cyclohexene. In particular, the directly measured photoionization spectrum of 2-cyclohexen-1-ol differs substantially from the previously calculated Franck-Condon envelope, and the product spectrum can be fit with no contribution from ring-opening. Measurements of H(2)O(2) photolysis in the presence of C(6)D(10) establish that the addition-elimination product incorporates the hydrogen atom from the hydroxyl radical reactant and loses a hydrogen (a D atom in this case) from the ring. Investigation of OH + cyclohexene-4,4,5,5-d(4) confirms this result and allows mass discrimination of different abstraction pathways. Products of 2-hydroxycyclohexyl-d(10) reaction with O(2) are observed upon adding a large excess of O(2) to the OH + C(6)D(10) system.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Cyclohexene, contains 100 ppm BHT as inhibitor, ≥99.0%
Sigma-Aldrich
Cyclohexene, inhibitor-free, ReagentPlus®, 99%
Supelco
Cyclohexene, analytical standard

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