Modeling deoxyribose radicals by neutralization-reionization mass spectrometry. Part 1. Preparation, dissociations, and energetics of 2-hydroxyoxolan-2-yl radical, neutral isomers, and cations

Journal of the American Society for Mass Spectrometry
Shetty VivekanandaFrantisek Turecek

Abstract

Collisional neutralization of several isomeric C(4)H(7)O(2) cations is used to generate radicals that share some structural features with transient species that are thought to be produced by radiolysis of 2-deoxyribose. The title 2-hydroxyoxolan-2-yl radical (1) undergoes nearly complete dissociation when produced by femtosecond electron transfer from thermal organic electron donors dimethyl disulfide and N,N-dimethylaniline in the gas phase. Product analysis, isotope labeling ((2)H and (18)O), and potential energy surface mapping by ab initio calculations at the G2(MP2) and B3-PMP2 levels of theory and in combination with Rice-Ramsperger-Kassel-Marcus (RRKM) kinetic calculations are used to assign the major and some minor pathways for 1 dissociations. The major (approximately 90%) pathway is initiated by cleavage of the ring C-5[bond]O bond in 1 and proceeds to form ethylene and *CH(2)COOH as main products, whereas loss of a hydrogen atom forms 4-hexenoic acid as a minor product. Loss of the OH hydrogen atom forming butyrolactone (2, approximately 9%) and cleavage of the C-3[bond]C-4 bonds (<1%) in 1 are other minor pathways. The major source of excitation in 1 is by Franck-Condon effects that cause substantial differences bet...Continue Reading

References

Nov 1, 1984·International Journal of Radiation Biology and Related Studies in Physics, Chemistry, and Medicine·C von Sonntag
Jun 1, 1995·International Journal of Radiation Biology·A O Colson, M D Sevilla
Feb 12, 2002·Journal of the American Society for Mass Spectrometry·Christopher J PetzoldHilkka I Kenttämaa
Oct 31, 2002·Journal of the American Chemical Society·Frantisek TurecekMiroslav Polásek
Feb 20, 2003·Journal of the American Chemical Society·Luis E Ramírez-ArizmendiHilkka I Kenttämaa
Mar 13, 2003·Journal of the American Chemical Society·Frantisek Turecek, Erik A Syrstad
Jul 1, 1992·Journal of the American Society for Mass Spectrometry·F TurecekS A Shaffer

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Citations

Jan 20, 2006·Journal of Mass Spectrometry : JMS·Xinli YangFrantisek Turecek
Dec 1, 2005·Journal of Mass Spectrometry : JMS·Michael Volný, Frantisek Turecek
May 10, 2005·Journal of Mass Spectrometry : JMS

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