DOI: 10.1021/ja017320i. Evidence for HOOO Radicals in the Formation of Alkyl Hydrotrioxides (ROOOH) and Hydrogen Trioxide (HOOOH) in the Ozonation of C−H Bonds in Hydrocarbons<sup>1</sup>

Evidence for HOOO Radicals in the Formation of Alkyl Hydrotrioxides (ROOOH) and Hydrogen Trioxide (HOOOH) in the Ozonation of C−H Bonds in Hydrocarbons1

10.1021/ja017320i

Crossref journal-article

American Chemical Society (ACS)

Journal of the American Chemical Society (316)

Authors 4

Janez Cerkovnik (first)
Evgen Eržen (additional)
Jože Koller (additional)
Božo Plesničar (additional)

References 35 Referenced 59

{'key': 'ja017320ib00001/ja017320ib00001_1', 'volume-title': 'Vienna, Austria', 'author': 'Cerkovnik J.', 'year': '2000'} / Vienna, Austria by Cerkovnik J. (2000)
{'key': 'ja017320ib00002/ja017320ib00002_1', 'first-page': '53', 'volume': '12', 'author': 'Kaufman M.', 'year': '1983', 'journal-title': 'Prog. React. Kinet.'} / Prog. React. Kinet. by Kaufman M. (1983)
10.1126/science.243.4892.745 / Science by Seinfeld J. H. (1989)
{'key': 'ja017320ib00002/ja017320ib00002_3', 'first-page': '770', 'volume': '243', 'author': 'McElroy M. B.', 'year': '1989', 'journal-title': 'J. Science'} / J. Science by McElroy M. B. (1989)
10.1126/science.1062722 / Science by Wentworth P. (2001)
{'key': 'ja017320ib00003/ja017320ib00003_2', 'volume-title': 'Oxygen Chemistry', 'author': 'Sawyer D. T.', 'year': '1991'} / Oxygen Chemistry by Sawyer D. T. (1991)
{'key': 'ja017320ib00004/ja017320ib00004_1', 'volume-title': 'Organic Peroxides', 'author': 'Plesničar', 'year': '1992'} / Organic Peroxides by Plesničar (1992)
{'key': 'ja017320ib00004/ja017320ib00004_2', 'volume-title': 'Organische Peroxo-Verbindungen', 'volume': '990', 'author': 'de Meijere A.'} / Organische Peroxo-Verbindungen by de Meijere A.
10.1021/ja981568z / J. Am. Chem. Soc. by Plesničar B. (1998)
10.1002/(SICI)1521-3765(20000303)6:5<809::AID-CHEM809>3.0.CO;2-8 / Chem.-Eur. J. by Plesničar B. (2000)
10.1126/science.285.5424.81 / Science by For (1999)
10.1021/jp981786e / J. Phys. Chem. A by Speranza M. (1998)
10.1021/ja00812a042 / J. Am. Chem. Soc. by Hellman T. M. (1974)
10.1021/ja00385a056 / J. Am. Chem. Soc. by For (1982)
10.1021/jo00188a012 / J. Org. Chem. by Pryor W. A. (1984)
10.1063/1.464304 / J. Chem. Phys. by Becke A. D. (1993)
10.1103/PhysRevB.37.785 / Phys. Rev. B by Lee C. (1988)
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A.GAUSSIAN98, Revision A.5; Gaussian: Pittsburgh, PA, 1998.
10.1016/S0009-2614(89)87395-6 / Chem. Phys. Lett. by Raghavachari K. (1989)
10.1021/jp993611q / J. Phys. Chem. A by Fenske J. D. (2000)
10.1021/ja000891a / J. Am. Chem. Soc. by Aloisio S. (2000)
Amour, T. S.; Fiat, D.Bull.Magn.Reson.1979,1, 118. Kintzinger, J.P. InNMR−Basic Principles and Progress; Diehl, P., Fluck, E., Kosfeld, R., Eds.; Springer: Berlin, 1981; Vol. 17, pp 1−64.
10.1021/ja00529a037 / J. Am. Chem. Soc. by Nangia P. S. (1980)
10.1021/ja9503387 / J. Am. Chem. Soc. by Koller J. (1996)
10.1021/jo00250a005 / J. Org. Chem. by Giamalva D. H. (1988)
10.1016/S0166-1280(99)00081-0 / J. Mol. Struct. (Theochem) by Timerghazin Q. K. (1999)
10.1021/ja00423a039 / J. Am. Chem. Soc. by Stary F. E. (1976)
10.1021/ja00504a031 / J. Am. Chem. Soc. by Kovac F. (1979)
10.1021/ja991001y / J. Am. Chem. Soc. by Aloisio S. (1999)
10.1063/1.1680001 / J. Chem Phys. by For (1973)
Binding energies of the HOOO•-HOH complex: B3LYP/6-311++G(2df,2p)(ZPE) = 5.0 kcal/mol; CCSD(T)/6-311++G(2df, 2p)//B3LYP/6-311++G(2df,2p) = 6.5 kcal/mol.24
For comparison, our CCSD(T)/6-311++G(d,p) calculations showed that the trans form of HOOO•was also slightly more stable (ΔE= 0.25 kcal/mol) than the cis isomer: (trans), H−O1= 0.970, O1−O2= 1.535, O2−O3= 1, 244, H−O1−O2= 98.1°, O1−O2−O3= 109.6°, H−O−O−O = 180°,E= −225.63351 au; (cis), H−O1= 0.974, O1−O2= 1.497, O2−O3= 1.261, H−O1−O2= 99.2°, O1−O2−O3= 111.8°, H−O−O−O = −9.9°,E= −225.63311 au.
10.1016/0301-0104(81)85090-2 / Chem. Phys. by Miertus S. (1981)
10.1021/cr960149m / Chem. Rev. by Cramer C. J. (1999)
10.1021/ja00013a034 / J. Am. Chem. Soc. by Plesničar B. (1991)

Dates

Type	When
Created	23 years, 1 month ago (July 26, 2002, 12:45 a.m.)
Deposited	2 years, 4 months ago (March 30, 2023, 3:45 p.m.)
Indexed	3 weeks, 4 days ago (Aug. 5, 2025, 8:47 a.m.)
Issued	23 years, 8 months ago (Dec. 28, 2001)
Published	23 years, 8 months ago (Dec. 28, 2001)
Published Online	23 years, 8 months ago (Dec. 28, 2001)
Published Print	23 years, 7 months ago (Jan. 1, 2002)

Funders 0

None

BibTeX

@article{Cerkovnik_2001, title={Evidence for HOOO Radicals in the Formation of Alkyl Hydrotrioxides (ROOOH) and Hydrogen Trioxide (HOOOH) in the Ozonation of C−H Bonds in Hydrocarbons1}, volume={124}, ISSN={1520-5126}, url={http://dx.doi.org/10.1021/ja017320i}, DOI={10.1021/ja017320i}, number={3}, journal={Journal of the American Chemical Society}, publisher={American Chemical Society (ACS)}, author={Cerkovnik, Janez and Eržen, Evgen and Koller, Jože and Plesničar, Božo}, year={2001}, month=dec, pages={404–409} }

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      "key": "ja017320ib00003/ja017320ib00003_2",
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      "author": "Sawyer D. T.",
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      "key": "ja017320ib00004/ja017320ib00004_1",
      "volume-title": "Organic Peroxides",
      "author": "Plesni\u010dar",
      "year": "1992"
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      "key": "ja017320ib00004/ja017320ib00004_2",
      "volume-title": "Organische Peroxo-Verbindungen",
      "volume": "990",
      "author": "de Meijere A."
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      "first-page": "8005",
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      "journal-title": "J. Am. Chem. Soc."
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      "first-page": "809",
      "DOI": "10.1002/(SICI)1521-3765(20000303)6:5<809::AID-CHEM809>3.0.CO;2-8",
      "volume": "6",
      "author": "Plesni\u010dar B.",
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      "journal-title": "Chem.-Eur. J."
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      "author": "Speranza M.",
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      "journal-title": "J. Phys. Chem. A"
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    {
      "key": "ja017320ib00007/ja017320ib00007_1",
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      "first-page": "1530",
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      "journal-title": "J. Am. Chem. Soc."
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      "journal-title": "J. Org. Chem."
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      "key": "ja017320ib00010/ja017320ib00010_1",
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      "DOI": "10.1063/1.464304",
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      "author": "Becke A. D.",
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      "DOI": "10.1103/PhysRevB.37.785",
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      "key": "ja017320ib00012/ja017320ib00012_1",
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      "first-page": "479",
      "DOI": "10.1016/S0009-2614(89)87395-6",
      "volume": "157",
      "author": "Raghavachari K.",
      "year": "1989",
      "journal-title": "Chem. Phys. Lett."
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    {
      "key": "ja017320ib00013/ja017320ib00013_1",
      "doi-asserted-by": "crossref",
      "first-page": "7246",
      "DOI": "10.1021/jp993611q",
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      "key": "ja017320ib00014/ja017320ib00014_1",
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      "first-page": "9196",
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    },
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      "key": "ja017320ib00015/ja017320ib00015_1",
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    {
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      "doi-asserted-by": "crossref",
      "first-page": "2470",
      "DOI": "10.1021/ja9503387",
      "volume": "118",
      "author": "Koller J.",
      "year": "1996",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ja017320ib00020/ja017320ib00020_1",
      "doi-asserted-by": "crossref",
      "first-page": "3429",
      "DOI": "10.1021/jo00250a005",
      "volume": "53",
      "author": "Giamalva D. H.",
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      "journal-title": "J. Org. Chem."
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    {
      "key": "ja017320ib00022/ja017320ib00022_1",
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      "first-page": "87",
      "DOI": "10.1016/S0166-1280(99)00081-0",
      "volume": "489",
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      "year": "1999",
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      "first-page": "1880",
      "DOI": "10.1021/ja00423a039",
      "volume": "98",
      "author": "Stary F. E.",
      "year": "1976",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ja017320ib00023/ja017320ib00023_2",
      "doi-asserted-by": "crossref",
      "first-page": "2677",
      "DOI": "10.1021/ja00504a031",
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      "author": "Kovac F.",
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      "journal-title": "J. Am. Chem. Soc."
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    {
      "key": "ja017320ib00024/ja017320ib00024_1",
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      "first-page": "8592",
      "DOI": "10.1021/ja991001y",
      "volume": "121",
      "author": "Aloisio S.",
      "year": "1999",
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    {
      "key": "ja017320ib00025/ja017320ib00025_1",
      "doi-asserted-by": "crossref",
      "first-page": "6220",
      "DOI": "10.1063/1.1680001",
      "volume": "59",
      "author": "For",
      "year": "1973",
      "journal-title": "J. Chem Phys."
    },
    {
      "key": "ja017320ib00026/ja017320ib00026_1",
      "unstructured": "Binding energies of the HOOO\u2022-HOH complex:\u2009 B3LYP/6-311++G(2df,2p)(ZPE) = 5.0 kcal/mol; CCSD(T)/6-311++G(2df, 2p)//B3LYP/6-311++G(2df,2p) = 6.5 kcal/mol.24"
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      "key": "ja017320ib00027/ja017320ib00027_1",
      "unstructured": "For comparison, our CCSD(T)/6-311++G(d,p) calculations showed that the trans form of HOOO\u2022was also slightly more stable (\u0394E= 0.25 kcal/mol) than the cis isomer:\u2009 (trans), H\u2212O1= 0.970, O1\u2212O2= 1.535, O2\u2212O3= 1, 244, H\u2212O1\u2212O2= 98.1\u00b0, O1\u2212O2\u2212O3= 109.6\u00b0, H\u2212O\u2212O\u2212O = 180\u00b0,E= \u2212225.63351 au; (cis), H\u2212O1= 0.974, O1\u2212O2= 1.497, O2\u2212O3= 1.261, H\u2212O1\u2212O2= 99.2\u00b0, O1\u2212O2\u2212O3= 111.8\u00b0, H\u2212O\u2212O\u2212O = \u22129.9\u00b0,E= \u2212225.63311 au."
    },
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      "key": "ja017320ib00028/ja017320ib00028_1",
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      "first-page": "117",
      "DOI": "10.1016/0301-0104(81)85090-2",
      "volume": "55",
      "author": "Miertus S.",
      "year": "1981",
      "journal-title": "Chem. Phys."
    },
    {
      "key": "ja017320ib00028/ja017320ib00028_2",
      "doi-asserted-by": "crossref",
      "first-page": "2161",
      "DOI": "10.1021/cr960149m",
      "volume": "99",
      "author": "Cramer C. J.",
      "year": "1999",
      "journal-title": "Chem. Rev."
    },
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      "first-page": "4946",
      "DOI": "10.1021/ja00013a034",
      "volume": "113",
      "author": "Plesni\u010dar B.",
      "year": "1991",
      "journal-title": "J. Am. Chem. Soc."
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