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@ARTICLE{Rissanen:187515,
      author       = {Rissanen, Matti P. and Kurtén, Theo and Sipilä, Mikko and
                      Thornton, Joel A. and Kangasluoma, Juha and Sarnela, Nina
                      and Junninen, Heikki and Jørgensen, Solvejg and Schallhart,
                      Simon and Kajos, Maija K. and Taipale, Risto and Springer,
                      Monika and Mentel, Thomas F. and Ruuskanen, Taina and
                      Petäjä, Tuukka and Worsnop, Douglas R. and Kjaergaard,
                      Henrik G. and Ehn, Mikael},
      title        = {{T}he {F}ormation of {H}ighly {O}xidized {M}ultifunctional
                      {P}roducts in the {O}zonolysis of {C}yclohexene},
      journal      = {Journal of the American Chemical Society},
      volume       = {136},
      number       = {44},
      issn         = {1520-5126},
      address      = {Washington, DC},
      publisher    = {American Chemical Society},
      reportid     = {FZJ-2015-01144},
      pages        = {15596 - 15606},
      year         = {2014},
      abstract     = {The prompt formation of highly oxidized organic compounds
                      in the ozonolysis of cyclohexene (C6H10) was investigated by
                      means of laboratory experiments together with quantum
                      chemical calculations. The experiments were performed in
                      borosilicate glass flow tube reactors coupled to a chemical
                      ionization atmospheric pressure interface time-of-flight
                      mass spectrometer with a nitrate ion (NO3–)-based
                      ionization scheme. Quantum chemical calculations were
                      performed at the CCSD(T)-F12a/VDZ-F12//ωB97XD/aug-cc-pVTZ
                      level, with kinetic modeling using multiconformer transition
                      state theory, including Eckart tunneling corrections. The
                      complementary investigation methods gave a consistent
                      picture of a formation mechanism advancing by peroxy radical
                      (RO2) isomerization through intramolecular hydrogen shift
                      reactions, followed by sequential O2 addition steps, that
                      is, RO2 autoxidation, on a time scale of seconds.
                      Dimerization of the peroxy radicals by recombination and
                      cross-combination reactions is in competition with the
                      formation of highly oxidized monomer species and is observed
                      to lead to peroxides, potentially diacyl peroxides. The
                      molar yield of these highly oxidized products (having O/C >
                      1 in monomers and O/C > 0.55 in dimers) from cyclohexene
                      ozonolysis was determined as (4.5 ± $3.8)\%.$ Fully
                      deuterated cyclohexene and cis-6-nonenal ozonolysis, as well
                      as the influence of water addition to the system (either H2O
                      or D2O), were also investigated in order to strengthen the
                      arguments on the proposed mechanism. Deuterated cyclohexene
                      ozonolysis resulted in a less oxidized product distribution
                      with a lower yield of highly oxygenated products and
                      cis-6-nonenal ozonolysis generated the same monomer product
                      distribution, consistent with the proposed mechanism and in
                      agreement with quantum chemical modeling.},
      cin          = {IEK-8},
      ddc          = {540},
      cid          = {I:(DE-Juel1)IEK-8-20101013},
      pnm          = {233 - Trace gas and aerosol processes in the troposphere
                      (POF2-233)},
      pid          = {G:(DE-HGF)POF2-233},
      typ          = {PUB:(DE-HGF)16},
      UT           = {WOS:000344516600029},
      pubmed       = {pmid:25283472},
      doi          = {10.1021/ja507146s},
      url          = {https://juser.fz-juelich.de/record/187515},
}