Kinetics of the Free-Radical Nonbranched-Chain Addition

Volume 2, Issue 2, April 2017     |     PP. 42-89      |     PDF (1204 K)    |     Pub. Date: June 19, 2017
DOI:    283 Downloads     4899 Views  

Author(s)

Michael M. Silaev, Chemistry Faculty, Lomonosov Moscow State University, Vorobievy Gory, Moscow 119991, Russia

Abstract
The aim of this study was the conclusion of simple kinetic equations to describe ab initio initiated nonbranched-chain processes of the saturated free-radical addition to the double bonds of unsaturated molecules in the binary reaction systems of saturated and unsaturated components. In the processes of this kind the formation rate of the molecular addition products (1:1 adducts) as a function of concentration of the unsaturated component has a maximum. Five reaction schemes are suggested for this addition processes. The proposed schemes include the reaction competing with chain propagation reactions through a reactive free radical. The chain evolution stage in these schemes involves three or four types of free radicals. One of them is relatively low-reactive and inhibits the chain process by shortening of the kinetic chain length. Based on the suggested schemes, nine rate equations (containing one to three parameters to be determined directly) are deduced using quasi-steady-state treatment. These equations provide good fits for the nonmonotonic (peaking) dependences of the formation rates of the molecular products (1:1 adducts) on the concentration of the unsaturated component in binary systems consisting of a saturated component (hydrocarbon, alcohol, etc.) and an unsaturated component (alkene, allyl alcohol, formaldehyde, or dioxygen). The unsaturated compound in these systems is both a reactant and an autoinhibitor generating low-reactive free radicals. A similar kinetic description is applicable to the nonbranched-chain process of the free-radical hydrogen oxidation, in which the oxygen with the increase of its concentration begins to act as an oxidation autoingibitor (or an antioxidant). The energetics of the key radical-molecule reactions is considered.

Keywords
Binary System, Unsaturated Compound, Low-Reactive Radical, Autoinhibitor, Competing Reaction, Non-Branched-Chain Addition, Kinetic Equa-tion, Rate, Parameters, Thermochemical Data, Energy.

Cite this paper
Michael M. Silaev, Kinetics of the Free-Radical Nonbranched-Chain Addition , SCIREA Journal of Chemistry. Volume 2, Issue 2, April 2017 | PP. 42-89.

References

[ 1 ] L. V. Gurvich, G. V. Karachevtsev, V. N. Kondrat'ev, Yu. A. Lebedev, V. A. Medvedev, V. K. Potapov, and Yu. S. Khodeev, “Energii razryva khimicheskikh svyazei. Potentsialy ionizatsii i srodstvo k elektronu” (“Bond Dissociation Energies, Ionization Potentials, and Electron Affinity”), V. N. Kondrat'ev, Editor, Nauka, Moscow, 1974.
[ 2 ] S. W. Benson, “Thermochemical Kinetics: Methods for the Estimation of Thermochemical Data and Rate Parameters”, 2nd Edition, Wiley, New York, 1976.
[ 3 ] J. B. Pedley, R. D. Naylor, and S. P. Kirby, “Thermochemical Data of Organic Com-pounds”, 2nd Edition, Chapman & Hall, London, 1986.
[ 4 ] Yu. D. Orlov, Yu. A. Lebedev, and I. Sh. Saifullin, “Termokhimiya organicheskikh svo-bodnykh radikalov” (“Thermochemistry of Organic Free Radicals”), A. M. Kutepov, Ed-itor., Nauka, Moscow, 2001.
[ 5 ] Ch. Walling, “Free Radicals in Solution”, Wiley, New York, 1956.
[ 6 ] N. M. Emanuel, E. T. Denisov, and Z. K. Maizus, “Tsepnye reaktsii okisleniya uglevo-dorodov v zhidkoi faze” (“Chain Oxidation Reactions of Hydrocarbons in the Liquid Phase”), Nauka, Moscow, 1965.
[ 7 ] V. A. Poluektov, E. I. Babkina, and I. R. Begishev, “On the Dependence of the Rate of a Chain Reaction on the Reactant Ratio”, Dokady Akademii Nauk SSSR, 1974, vol. 215, no. 3, pp. 649–652.
[ 8 ] M. M. Silaev and L. T. Bugaenko, “Mathematical Simulation of the Kinetics of Radiation Induced Hydroxyalkylation of Aliphatic Saturated Alcohols”, Radiation Physics and Chemistry, 1992, vol. 40, no. 1, pp. 1–10.
[ 9 ] M. M. Silaev and L. T. Bugaenko, “Kinetics of the Addition of α-Hydroxyalkyl Radicals to 2-Propen-1-ol and Formaldehyde”, Kinetics and Katalysis, 1994, vol. 35, no. 4, pp. 509–513.
[ 10 ] M. M. Silaev, “Competition Kinetics of Nonbranched Chain Processes of Free-Radical Addition to Double Bonds of Molecules with the Formation of 1:1 Adducts”, Kinetica i Kataliz., 1999, vol. 40, no. 2, pp. 281–284, English Translation in: Kinetics and Catalysis, 1999, vol. 40, no. 2, pp. 256–259.
[ 11 ] M. M. Silaev, “Simulation of the Nonbranched-Chain Addition of Saturated Free Radicals to Alkenes and Their Derivatives Yielding 1:1 Adducts”, Teoreticheskie Osnovy Khimicheskoi Tekhnologii, Vol. 41, No. 3, 2007, pp. 280–295, English Translation in: Theoretical Foundations of Chemical Engineering, 2007, vol. 41, no. 3, pp. 273–278.
[ 12 ] M. M. Silaev, “Simulation of Nonbranched Chain Processes for Producing 1,2-Alkanediols in Alcohol–Formaldehyde Systems”, Teoreticheskie Osnovy Khimicheskoi Tekhnologii, 2007, vol. 41, no. 4, pp. 379–384, English Translation in: Thoretical Foundations Chemical Engineering, 2007, vol. 41, no. 4, pp. 357–361.
[ 13 ] M. M. Silaev, “A New Competitive Kinetic Model of Radical Chain Oxidation: Oxygen as an Autoinhibitor”, Biofizika, Vol. 46, No. 2, 2001, pp. 203–209, English Translation in: Biophysics, Vol. 46, No. 2, 2001, pp. 202–207.
[ 14 ] M. M. Silaev, “Simulation of the Initiated Addition of Hydrocarbon Free Radicals and Hydrogen Atoms to Oxygen via a Nonbranched Chain Mechanism”, Teoreticheskie Osnovy Khimicheskoi Tekhnologii, Vol. 41, No. 6, 2007, pp. 634–642, English Translation in: Theoretical Foundation of Chemical Engineering, Vol. 41, No. 6, 2007, pp. 831–838.
[ 15 ] Y. Bard, “Nonlinear Parameter Estimation”, Academic, New York, 1974.
[ 16 ] L. Bateman, “Alkene Oxidation”, Quarterly Reviews, Vol. 8, No. 2, 1954, pp. 147–167.
[ 17 ] W. H. Urry, F. W. Stacey, E. S. Huyser, and O. O. Juveland, “The Peroxide- and Light-Induced Additions of Alcohols to Alkenes”, Journal of the American Chemical So-ciety, Vol. 76, No. 2, 1954, pp. 450–455.
[ 18 ] Urry, W.H. and Juveland, O.O., “Free Radical Additions of Amines to Alkenes”, Journal of the American Chemical Society, Vol. 80, No. 13, 1958, pp. 3322–3328.
[ 19 ] A. G. Shostenko, P. A. Zagorets, A. M. Dodonov, and A. A. Greish, “γ-Radiation-Induced Addition of Phosphorus Trichloride to Isobutylene”, Khimiya Vysokikh Energii, Vol. 4, No. 4, 1970, p. 357.
[ 20 ] V. Kim, A. G. Shostenko, and M. D. Gasparyan, “Reactivity of Polychloroalkyl Radicals in the Telomerization of CCl4 with 1-Propene and 2-Methyl-1-Propene” (in Russian), Reaction Kinetics and Catalysis Letters, Vol. 12, No. 4, 1979, pp. 479–484.
[ 21 ] V. E. Myshkin, A. G. Shostenko, P. A. Zagorets, K. G. Markova, and A. I. Pchelkin, “Determination of Absolute Rate Constants for the Addition of the Ethyl Radical to Al-kenes”, Teoreticheskaya i Eksperimental’naya Khimiya, Vol. 13, No. 2, 1977, pp. 266–271.
[ 22 ] R. A. Zamyslov, A. G. Shostenko, I. V. Dobrov, and N. P. Tarasova, “Kinetics of γ-Radiation-Induced Reactions of 2-Propanol with Trifluoropropene and Hex-aflu-oropropene”, Kinetika i Katalyz., Vol. 28, No. 4, 1987, pp. 977–979.
[ 23 ] M. M. Silaev, “Dependence of Radiation-chemical γ-Diol Yields on the 2-Propen-1-ol Concentration in the Radiolysis of Aliphatic Saturated C1-C3 Alcohol + 2-Propen-1-ol Systems”, Khimiya Vysokikh Energii, Vol. 24, No. 3, 1990, pp. 282–283.
[ 24 ] M. M. Silaev, “γ-Diol Formation via the Autooxidation of 2-Propen-1-ol Solutions in Saturated Alcohols”, Vestnik Moskovskogo Universiteta, Ser. 2: Khimiya, Vol. 35, No. 1, 1994, pp. 40–42.
[ 25 ] L. T. Bugaenko, M. G. Kuzmin, and L. S. Polak, “High-Energy Chemistry”, Horwood Hall, New York, 1993, p. 112.
[ 26 ] J. K. Thomas, “Pulse Radiolysis of Aqueous Solutions of Methyl Iodide and Methyl Bromide. The Reactions of Iodine Atoms and Methyl Radicals in Water” The Journal of the Physical Chemistry, Vol. 71, No. 6, 1967, pp. 1919–1925.
[ 27 ] J. F. Walker, Formaldehyde, Reinhold, New York, 1953, English Translation under the title Formal’degid, Goskhimizdat, Moscow, 1957, p. 106.
[ 28 ] M. M. Silaev, A. V. Rudnev, and E. P. Kalyazin, “Formaldehyde. III. Concentration of Free Formaldehyde as a Function of Temperature, Polarity of Solvents, and Total Con-centration of Formaldehyde in Solution”, Zhurnal Fizicheskoi Khimii, Vol. 53, No. 7, 1979, pp. 1647–1651.
[ 29 ] Oyama, M., “A Free-Radical Reaction of Primary and Secondary Alcohols with Formal-dehyde”, The Journal of Organic Chemistry, Vol. 30, No. 7, 1965, pp. 2429–2432.
[ 30 ] G. I. Nikishin, D. Lefor, and E. D. Vorob’ev, “Free Radical Reaction of Primary Alcohols with Formaldehyde”, Izvestiya Akademii Nauk SSSR, Ser. Khimiya, No. 7, 1966, pp. 1271–1272.
[ 31 ] M. B. Dzhurinskaya, A. V. Rudnev, and E. P. Kalyazin, “High Temperature UV Photolysis of Formaldehyde in Liquid Methanol”, Vestnik Moskovskogo Universiteta, Ser. 2: Khimiya, Vol. 25, No. 2, 1984, pp. 173–176.
[ 32 ] E. P. Kalyazin, E. P. Petryaev, and O. I Shadyro, “Reaction between Oxyalkyl Radicals and Aldehydes”, Zhurnal Organicheskoi Khimii, Vol. 13, No. 2, 1977, pp. 293–295.
[ 33 ] A. I. Novoselov, A.I., Silaev, M.M., and L. T. Bugaenko, “Effect of Temperature on the Yields of Final Products in the γ-Radiolysis of Formaldehyde Solutions in C1-C3 Alkanols”, Khimiya Vysokich Energii, Vol. 38, No. 4, 2004, pp. 270–272, English Translation in: High Energy Chemistry, Vol. 38, No. 4, 2004, pp. 236–238.
[ 34 ] A. I. Novoselov, M. M. Silaev, and L. T. Bugaenko, “Dependence of Ethanediol Yield on Formaldehyde Concentration in γ-Radiolysis of Methanol–Formaldehyde System at 373–473 K”, Khimiya Vysokikh Energii, Vol. 42, No. 1, 2008, pp. 74–75, English Trans-lation in: High Energy Chemistry, vol. 42, no. 1, 2008, pp. 69–70.
[ 35 ] A. I. Novoselov, M. M. Silaev, and L. T. Bugaenko, “γ-Induced Single-Step Synthesis of Ethylene Glycol from Methanol–Formaldehyde Solution”, Theoreticheskie Osnovy Khimicheskoy Tekhnologii, Vol. 44, No. 4, 2010, pp. 450–453, English Translation in: Theoretical Foundation of Chemical Engineering, Vol. 44, No. 4, 2010, pp. 432–435.
[ 36 ] A. I. Novoselov, M. M. Silaev, and L. T. Bugaenko, “Dependence of 1,2-Propanediol Yield on Formaldehyde Concentration in γ-Radiolysis of Ethanol–Formaldehyde System at 373¬473 K”, Khimiya Vysokikh Energii, Vol. 41, No. 1, 2007, p. 58, English Translation in: High Energy Chemistry, Vol. 41, No. 1, 2007, p. 53.
[ 37 ] S. Ya. Pshezhetskii, A. G. Kotov, V. K. Milinchuk, V. A. Roginskii, and V. I. Tupikov, “EPR svobodnykh radikalov v radiatsionnoi khimii” (“ESR of Free Radicals in Radiation Chemistry”), Khimiya, Moscow, 1972.
[ 38 ] M. M. Silaev, “Estimating the Solvent Concentration in Formaldehyde Solutions at Various Temperatures”, Zhurnal Fizicheskoy Khimii, Vol. 67, No. 9, 1993, p. 1944.
[ 39 ] M. M. Silaev, “Applied Aspects of the γ-Radiolysis of C1-C4 Alcohols and Binary Mixtures on Their Basis”, Khimiya Vysokikh Energii, Vol. 36, No. 2, 2002, pp. 97–101, English Translation in: High Energy Chemistry, Vol. 36, No. 2, 2002, pp. 70–74.
[ 40 ] M. M. Silaev, L. T. Bugaenko, and E. P. Kalyazin, “On the Possibility of Adequately Es-timating the Rate Constants for the Reaction of Hydroxyalkyl Radicals with Each Other Using the Self-Diffusion Coefficients or Viscosities of the Corresponding Alcohols”, Vestnik Moskovskogo. Univiversiteta, Ser. 2: Khimiya, Vol. 27, No. 4, 1986, pp. 386–389.
[ 41 ] O. I. Shadyro, “Radiation-chemical Conversions of Aldehydes in Various Systems”, Ph.D. Thesis (Chemistry), Belarusian State University, Minsk, 1975.
[ 42 ] M. M. Silaev, “Relative Reactivity of α-Hydroxyethyl Radicals for 2-Propene-1-ol and Formaldehyde Double-Bond Addition”, Vestnik Moskovskogo Universiteta, Ser. 2: Khimiya, Vol. 34, No. 3, 1993, p. 311.
[ 43 ] H. Seki, R. Nagai, and M. Imamura, “γ-Radiolysis of a Binary Mixture of Methanol and Water. The Formation of Formaldehyde in the Radiolysis of Liquid Methanol”, Bulletin of the Chemical Society of Japan., Vol. 41, No. 12, 1968, pp. 2877–2881.
[ 44 ] V. Ya. Shtern, “Mekhanizm okisleniya uglevodorodov v gazovoi faze (Mechanism of the Gas-Phase Oxidation of Hydrocarbons)”, Akademiya Nauk SSSR, Moscow, 1960.
[ 45 ] H. L. J. Bäckström, “Der Kettenmechanismus bei der Autoxydation von Aldehyden”, Zeitschrift für physikalische Chemie (B)”, Bd. 25, № 1–2, 1934, Sn. 99–121.
[ 46 ] A. A. Aliev, and V. V. Saraeva, “Isomerization of Peroxy Radicals Resulting from the Radiation-Induced Oxidation of o-Xylene”, Vestnik Moskovskogo Universiteta, Ser. 2: Khimiya, Vol. 34, No. 4, 1983, pp. 371–374.
[ 47 ] E. J. Badin, “The Reaction between Atomic Hydrogen and Molecular Oxygen at Low Pressures. Surface Effects”, Journal of the American Chemistry Society, Vol. 70, No. 11, 1948, pp. 3651–3655.
[ 48 ] A. L. Buchachenko, “Kompleksy radikalov i molekulyarnogo kisloroda s organicheskimi molekulami” (“Complexes of Radicals and Dioxygen with Organic Molecules”), I. P. Beletskaya, Editor, Nauka, Moscow, 1984.
[ 49 ] J. S. Francisco and I. H. Williams, “The Thermochemistry of Polyoxides and Polyoxy Radicals”, International Journal of Chemical Kinetics, Vol. 20, No. 6, 1988, pp. 455–466.
[ 50 ] V. N. Kokorev, N. N. Vyshinskii, V. P. Maslennikov, I. A. Abronin, G. M. Zhidomirov, and Yu. A. Aleksandrov, “Electronic Structure and Chemical Reactions of Peroxides: I. MINDO/3 Calculation of the Geometry and Enthalpy of Formation of the Ground States of Organic and Organoelement Peroxides”, Zhurnal Strukturnoi Khimii, Vol. 22, No. 4, 1981, pp. 9–15.
[ 51 ] A. F. Dmitruk, V. V. Lobanov, and L. I. Kholoimova, “Role of Tetroxide Conformation in the Mechanism of Peroxy Radical Recombination”, Teoreticheskaya i Eksperimental’naya Khimiya, Vol. 22, No. 3, 1986, pp. 363–366.
[ 52 ] V. A. Belyakov, R. F. Vasil'ev, N. M. Ivanova, B. F. Minaev, O. V. Osyaeva, and G. F. Fedorova, “Electronic Model of the Excitation of Chemiluminescence in the Oxidation of Organic Compounds”, Izvestiya Akademii Nauk SSSR, Ser.: Fizika, Vol. 51, No. 3, 1987, pp. 540–547.
[ 53 ] P. Ase, W. Bock, and A. Snelson, “Alkylperoxy and Alkyl Radicals. 1. Infrared Spectra of CH3O2 and CH3O4CH3 and the Ultraviolet Photolysis of CH3O2 in Argon + Oxygen Ma-trices”, The Journal of Physical Chemistry, Vol. 90, No. 10, 1986, pp. 2099–2109.
[ 54 ] G. C. Pimentel and A. L. McClellan, “The Hydrogen Bond”, L. Pauling, Editor, Freeman, San Francisco, 1960, p. 200.
[ 55 ] G. A. Russell, “Deuterium-Isotope Effects in the Autooxidation of Aralkyl Hydrocarbons: Mechanism of the Interaction of Peroxy Radicals”, Journal of the American Chemical Society, Vol. 79, No. 14, 1957, pp. 3871–3877.
[ 56 ] M. M. Silaev, “The Competition Kinetics of Nonbranched Chain Processes of Free-Radical Addition to Double Bonds of Molecules with the Formation of 1:1 Adducts and the In-hibition by the Substrate”, Oxidation Communication, Vol. 22, No. 2, 1999, pp. 159–170.
[ 57 ] M. M. Silaev, “The Competition Kinetics of Radical-Chain Addition”, Zhurnal Fizicheskoi Khimii, Vol. 73, No. 7, 1999, pp. 1180–1184, English Translation in: Russian Journal of Physical Chemistry, Vol. 73, No. 7, 1999, pp. 1050–1054.
[ 58 ] A. P. Darmanyan, D. D. Gregory, Y. Guo, W. S. Jenks, L. Burel, D. Eloy, and P. Jardon, “Quenching of Singlet Oxygen by Oxygen- and Sulfur-Centered Radicals: Evidence for Energy Transfer to Peroxy Radicals in Solution”, Journal of the American Chemistry Society, Vol. 120, No. 2, 1998, pp. 396–403.
[ 59 ] J. R. Kanofsky, “Singlet Oxygen Production from the Reactions of Alkylperoxy Radicals. Evidence from 1268-nm Chemiluminescence”, The Journal of Organic Chemistry, Vol. 51, No. 17, 1986, pp. 3386–3388.
[ 60 ] N. N. Semenov, “Tsepnye reaktsii” (“Chain Reactions”), Goskhimtekhizdat, Leningrad, 1934, pp. 241, 203.
[ 61 ] M. Reznikovskii, Z. Tarasova, and B. Dogadkin, “Oxygen Solubility in Some Organic Liquids”, Zhurnal Obshchei Khimii, Vol. 20, No. 1, 1950, pp. 63–67.
[ 62 ] J. A. Howard and K. U. Ingold, “Absolute Rate Constants for Hydrocarbon Autooxidation. VI. Alkyl Aromatic and Alkeneic Hydrocarbons”, Canadian Journal of Chemistry, Vol. 45, No. 8, 1967, pp. 793–802.
[ 63 ] N. F. Barr and A. O. Allen, “Hydrogen Atoms in the Radiolysis of Water”, The Journal of Physical Chemistry, Vol. 63, No. 6, 1959, pp. 928–931.
[ 64 ] H. A. Smith and A. Napravnik, “Photochemical Oxidation of Hydrogen”, Journal of the American Chemistry Society, Vol. 62, No. 1, 1940, pp. 385–393.
[ 65 ] P. B. Pagsberg, J. Eriksen, and H. C. Christensen, “Pulse Radiolysis of Gaseous Ammo-nia–Oxygen Mixtures”, The Journal of Physical Chemistry, Vol. 83, No. 5, 1979, pp. 582–590.
[ 66 ] M. M. Silaev, “Competitive Mechanism of the Non-branched Radical Chain Oxidation of Hydrogen Involving the Free Cyclohydrotetraoxyl Radical [ОО···Н···ОО]•, Which Inhibits the Chain Process”, “Khimiya Vysokikh Energii, Vol. 37, No. 1, 2003, pp. 27–32, English Translation in: High Energy Chemistry, Vol. 37, No. 1, 2003, pp. 24–28.
[ 67 ] M. M. Silaev, “Simulation of Initiated Nonbranched Chain Oxidation of Hydrogen: Ox-ygen as an Autoinhibitor”, Khimiya Vysokich Energii, Vol. 42, No. 2, 2008, pp. 124–129, English Translation in: High Energy Chemistry, Vol. 42, No. 1, 2008, pp. 95–100.
[ 68 ] D. J. McKay and J. S. Wright, “How Long Can You Make an Oxygen Chain?”, Journal of the American Chemistry Society, Vol. 120, No. 5, 1998, pp. 1003–1013.
[ 69 ] N. P. Lipikhin, “Dimers, Clusters, and Cluster Ions of Oxygen in the Gas Phase”, Uspekhi Khimii, Vol. 44, No. 8, 1975, pp. 366–376.
[ 70 ] S. D. Razumovskii, “Kislorod – elementarnye formy i svoistva” (“Oxygen: Elementary Forms and Properties”), Khimiya, Moscow, 1979.
[ 71 ] K. M. Dunn, G. E. Scuceria, and H. F. Schaefer III, “The infrared spectrum of cyclo-tetraoxygen, O4: a theoretical investigation employing the single and double excitation coupled cluster method”, The Journal of Chemical Physics, Vol. 92, No. 10, 1990, pp. 6077–6080.
[ 72 ] L. Brown and V. Vaida, “Photoreactivity of Oxygen Dimers in the Ultraviolet”, The Journal of Physical Chemistry, Vol. 100, No. 19, 1996, pp. 7849–7853.
[ 73 ] V. Aquilanti, D. Ascenzi, M. Bartolomei, D. Cappelletti, S. Cavalli, M. de Castro-Vitores, and F. Pirani, “Molecular Beam Scattering of Aligned Oxygen Molecules. The Nature of the Bond in the O2–O2 Dimer”, Journal of the American Chemistry Society, Vol. 121, No. 46, 1999, pp. 10794–1080.
[ 74 ] F. Cacace, G. de Petris, and A. Troiani, “Experimental Detection of Tetraoxygen”, An-gewandte Chemie, Internation Edition (in English), Vol. 40, No. 21, 2001, pp. 4062–4065.
[ 75 ] H. S. Taylor, “Photosensitisation and the Mechanism of Chemical Reactions”, Transactions of the Faraday Society, Vol. 21, No. 63 (3), 1926, pp. 560–568.
[ 76 ] A. B. Nalbandyan and V. V. Voevodskii, “Mekhanizm okisleniya i goreniya vodoroda” (“Mechanism of Hydrogen Oxidation and Combustion”), V. N. Kondrat'ev, Editor, Akad. Nauk SSSR, Moscow, 1949.
[ 77 ] S. N. Foner and R. L. Hudson, “Mass spectrometry of the HO2 free radical”, The Journal of Chemical Physics, Vol. 36, No. 10, 1962, p. 2681.
[ 78 ] C. J. Hochanadel, J. A. Ghormley, and P. J. Ogren, “Absorption Spectrum and Reaction Kinetics of the HO2 Radical in the Gas Phase”, The Journal of Chemical Physics, Vol. 56, No. 9, 1972, pp. 4426–4432.
[ 79 ] J. B. Robertson, “A Mass Spectral Search for H2O4 and HO4 in a Gaseous Mixture Con-taining HO2 and O2”, Chemistry and Industry, 1954, no. 48, p. 1485.
[ 80 ] D. Bahnemann and E. J. Hart, “Rate Constants of the Reaction of the Hydrated Electron and Hydroxyl Radical with Ozone in Aqueous Solution”, The Journal of Physical Chem-istry, Vol. 86, No. 2, 1982, pp. 252–255.
[ 81 ] “Vodorodnaya svyaz’: Sbornik statei” (“The Hydrogen Bonding: Collection of Articles”) N. D. Sokolov, Editor, Nauka, Moscow, 1981.
[ 82 ] J. Staehelin, R. E. Bühler, and J. Hoigné, “Ozone Decomposition in Water Studied by Pulse Radiolysis. 2. OH and HO4 as Chain Intermediates”, The Journal of Physical Chemistry, Vol. 88, no. 24, 1984, pp. 5999–6004.
[ 83 ] F. Cacace, G. de Petris, F. Pepi, and A. Troiani, “Experimental Detection of Hydrogen Trioxide”, Science, Vol. 285, No. 5424, 1999, pp. 81–82.
[ 84 ] R. F. Bühler, J. Staehelin, and J. Hoigné, “Ozone Decomposition in Water Studied by Pulse Radiolysis. 1. HO2/O2– and HO3/O3– as Intermediates”, The Journal of Physical Chemistry, Vol. 88, No. 12, 1984, pp. 2560–2564.
[ 85 ] I. V. Trushkov, M. M. Silaev, and N. D. Chuvylkin, “Acyclic and Cyclic Forms of the Radicals , , and : Ab Initio Quantum Chemical Calculations”, Izvestiya Akademii Nauk, Ser.: Khimiya, No. 3, 2009, pp. 479–482, English Translation in: Russian Chemical Bulletin, International Edition, Vol. 58, No. 3, 2009, pp. 489–492.
[ 86 ] A. Mansergas, J. M. Anglada, S. Olivella, M. F. Ruiz-López, “On the Nature of the Unu-sually Long OO Bond in HO3 and HO4 Radicals”, Phys. Chem. Chem. Phys., Vol. 9, No. 44, 2007, pp. 5865–5873.
[ 87 ] W. Wong and D. D. Davis, “A Flash Photolysis Resonance Fluorescence Study of the Reactions of Atomic Hydrogen and Molecular Oxygen: H + O2 + M → HO2 + M”, Inter-national Journal of Chemical Kinetics, Vol. 6, No. 3, 1974, pp. 401–416.
[ 88 ] X. Xu, R. P. Muller, and W. A. Goddard III, “The Gas Phase Reaction of Singlet Dioxygen with Water: a Water-Catalyzed Mechanism”, Proceedings of the National Academy Sci-ences of the United States of America, Vol. 99, No. 6, 2002, pp. 3376–3381.
[ 89 ] E. T. Seidl and H. F. Schaefer III, “Is There a Transition State for the Unimolecular Dis-sociation of Cyclotetraoxygen (O4)?”, The Journal of Chemical Physics, Vol. 96, No. 2, 1992, pp. 1176–1182.
[ 90 ] R. Hernández-Lamoneda and A. Ramírez-Solís, “Reactivity and Electronic States of O4 along Minimum Energy Paths”, The Journal of Chemical Physics, Vol. 113, No. 10, 2000, pp. 4139–4145.
[ 91 ] A. J. C. Varandas and L. Zhang, “Test Studies on the Potential Energy Surface and Rate Constant for the OH + O3 Atmospheric Reaction”, Chemical Physics Letters, Vol. 331, Nos. 5–6, 2000, pp. 474–482.
[ 92 ] “Atmosfera. Spravochnik” (“Atmosphere: A Handbook”), Gidrometeoizdat, Leningrad, 1991.
[ 93 ] H. Okabe, “Photochemistry of Small Molecules”, Wiley, New York, 1978.
[ 94 ] A. K. Pikaev, “Sovremennaya radiatsionnaya khimiya. Radioliz gazov i zhidkostei” (“Modern Radiation Chemistry: Radiolysis of Gases and Liquids”), Nauka, Moscow, 1986.
[ 95 ] A. W. Boyd, C. Willis, and O. A. Miller, “A Re-examination of the Yields in the High Dose Rate Radiolysis of Gaseous Ammonia”, Canadian Journal of Chemistry, Vol. 49, No. 13, 1971, pp. 2283–2289.
[ 96 ] M. M. Silaev, “Competition Mechanism of Substrate-Inhibited Radical Chain Addition to Double Bond”, Neftekhimiya, Vol. 40, No. 1, 2000, pp. 33–40, English Translation in: Peroleum Chemistry, Vol. 40, No. 1, 2000, pp. 29–35.
[ 97 ] M. M. Silaev, “Competition Kinetics of Nonbranched Chain Processes of Free Radical Addition to the C=C, C=O, and O=O Double Bonds of Molecules”, Neftekhimiya, Vol. 43, No. 4, 2003, pp. 302–307, English Translation in: Petroleum Chemistry, vol. 43, no. 4, 2003, pp. 258–273.
[ 98 ] M. M. Silaev, “Low-reactive Free Radicals Inhibiting Nonbranched Chain Processes of Addition”, Biofizika, Vol. 50, No. 4, 2005, pp. 585–600, English Translation in: Biophysics, Vol. 50, No. 4, 2005, pp. 511–524.
[ 99 ] R. T. Sanderson, “Radical Reorganization and Bond Energies in Organic Molecules”, The Journal of Organic Chemistry, Vol. 47, No. 20, 1982, pp. 3835–3839.
[ 100 ] I. V. Vereshchinskii and A. K. Pikaev, “Vvedenie v radiatsionnuyu khimiyu” (“Introduc-tion to Radiation Chemistry”), Spitsyn, V.I., Editor, Akademiya Nauk SSSR, Moscow, 1963, p. 190.