Features of mechanism of free radical initiation in polymers under exposure to nitrogen oxides
E. Y. Davydov
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia
Search for more papers by this authorI. S. Gaponova
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia
Search for more papers by this authorT. V. Pokholok
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia
Search for more papers by this authorA. P. Vorotnikov
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia
Search for more papers by this authorCorresponding Author
G. B. Pariiskii
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia.Search for more papers by this authorG. E. Zaikov
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia
Search for more papers by this authorE. Y. Davydov
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia
Search for more papers by this authorI. S. Gaponova
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia
Search for more papers by this authorT. V. Pokholok
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia
Search for more papers by this authorA. P. Vorotnikov
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia
Search for more papers by this authorCorresponding Author
G. B. Pariiskii
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia.Search for more papers by this authorG. E. Zaikov
Emanuel Institute of Biochemical physics, Russian Academy of Sciences, 4 Kosygin Street. 119334 Moscow, Russia
Search for more papers by this authorAbstract
The mechanism of interactions of NO, NO2, NO3 as well as dimers of NO2 with functional groups of organic molecules and polymers is considered. It is shown that nitrogen oxides are active initiators of radical reactions as a result of which various molecular products of nitration and stable nitrogen-containing radicals are formed. Features of the initiation mechanism determining the composition of molecular and radical products of conversions of the compounds on exposure to nitrogen oxides have been revealed. Copyright © 2008 John Wiley & Sons, Ltd.
REFERENCES
- 1 Graham RA, Johnston HS. J. Phys. Chem. 1978; 82(3): 254.
- 2 Johnston HS, Graham RA. Can. J. Chem. 1974; 52(8): 1415.
- 3 Stroud C, Madronich S, Atlas E, Ridley B, Flocke F, Tallot AW, Fried A, Wert B, Shetter R, Lefler B, Coffey M, Heik B. Atmos. Environ. 2003; 37(24): 3351.
- 4 Tong DQ, Kang D, Aneja VP, Ray JD. Atmos. Environ. 2005; 39(2): 315.
- 5 Titov AI. Tetrahedron 1963; 19: 557.
- 6 Topchiev AV. Nitration of Hydrocarbons and Other Organic Compounds. Academy of Sciences of the USSR: Moscow, 1956.
- 7 Novikov SS, Shveyhgeymer GA, Sevastyanova VV, Shlyapochnikov VA. Chemistry of Aliphatic Alicyclic Nitro Compounds. Khimiya: Moscow, 1974.
- 8 Pariiskii GB, Gaponova IS, Davydov EYa. Russ. Chem. Rev. 2000; 69(11): 985.
- 9 Pariiskii GB, Gaponova IS, Davydov E Ya, Pokholok TV. Aging of Polymers, Polymer Blends and Polymer Composites, GE Zaikov, AL Buchachenko, VB Ivanov (eds). Nova Science Publishers: New York, 2002; 31–43.
- 10 Vasserman AM, Kovarsky AL. Spin Labels and Spin Probes in Physical Chemistry of Polymers. Nauka: Moscow, 1986.
- 11 Gaponova IS, Davydov E Ya, Pariiskii GB, Pustoshny VP. Vysokomol. Soed., Ser. A 2001; 43(1): 98.
- 12 Pokholok TV, Gaponova IS, Davydov EYa, Pariiskii GB. Polym. Degrad. Stab. 2006; 91(10): 2423.
- 13 Bonner FT, Stedman G. Methods in Nitric Oxide Research, M Feelish, JS Stamler (eds). Wiley: Chichester, 1996; 3–17.
- 14 Rånby B, Rabek JF. Photodegradation, Photo-oxidation and Photostabilization of Polymers. Wiley: London, 1975.
- 15 Park JSB, Walton JC. J. Chem. Soc. Perkin Trans. 1997; 2: 2579.
- 16 Gaponova IS, Pariiskii GB, Toptygin DYa. Vysokomolek. Soed. 1988; 30(2): 262.
- 17 Gaponova IS, Pariiskii GB, Toptygin DYa. Khim. Fiz. 1997; 16(10): 49.
- 18 Neta P, Huie RE. J. Phys. Chem. 1986; 90(19): 4644.
- 19 Vencatachalapathy B, Ramamurthy R. J. Photochem. Photobiol. A: Chem. 1996; 93: 1.
- 20 Japar SM, Niki HH. J. Phys. Chem. 1975; 79(16): 1629.
- 21 Atkinson R, Plum CN, Carter WPL, Winer AM, Pitts JN. J. Phys. Chem. 88(6): 1210.
- 22 Itho O, Akiho S, Iino M. J. Org. Chem. 1989; 54(10): 2436.
- 23 Pikaev AK, Sibirskaya GK, Shyrshov EM, Glazunov PYa, Spicyn VI. Dokl. Akad. Nauk SSSR 1974; 215(3): 645.
- 24 Hayon E, Saito E. J. Chem Phys. 1965; 43(12): 4314.
- 25 Dagliotti L, Hayon E. J. Phys. Chem. 1967; 71(12): 3802.
- 26 Glass PW, Martin TW. J. Am. Chem. Soc. 92(17): 5084.
- 27 Wine PH, Mauldin RL, Thorn RP. J. Phys. Chem. 1988; 92(5): 1156.
- 28 Davydov EYa, Afanas'eva EN, Gaponova IS, Pariiskii GB. Org. Biomol. Chem. 2004; 2(9): 1339.
- 29 Davydov EYa, Gaponova IS, Pariiskii GB. Vysokomolek. Soed., Ser. A 2003; 45(4): 581.
- 30 Naghash HJ, Massah A, Erfan A. Eur. Polym. J. 2002; 38(1): 147.
- 31 Jellinek HHG. Aspects of Degradation and Stabilization of Polymers. Elsevier: New York, 1978; Chapter 9.
- 32 Giamalva DH, Kenion GB, Pryor WA. J. Am. Chem. Soc. 1987; 109(23): 7059.
- 33 Golding P, Powell JL, Ridd JH. J. Chem. Soc. Perkin Trans. 1996; 2: 813.
- 34 Gyor M, Rockenbauer A, Tüdos F. Tetrahedron Lett. 1986; 27(39): 4795.
- 35 Pokholok TV, Pariiskii GB. Vysokomolek. Soed., Ser. A 1977; 39(7): 1152.
- 36 Smirnov AI, Degtyarev EN, Yakimchenko OE, Lebedev YaS. Pribory Tekhn. Eksperim. 1991; 1: 195.
- 37 Degtyarev EN, Pokholok TV, Pariiskii GB, Yakimchenko OE. Zh. Fiz. Khim. 1994; 68(3): 461.
- 38 McKee ML. J. Am. Chem. Soc. 1995; 117(8): 1629.
- 39 White EH. J. Am. Chem. Soc. 1955; 77(20): 6008.
- 40 Davydov EYa, Gaponova IS, Pariiskii GB, Pokholok TV. Polym. Sci., Ser. A 2006; 48(4): 375.
- 41 Feuer H. The Chemistry of the Nitro and Nitroso Groups. Wiley: New York, 1969.
- 42 Davydov EYa, Gaponova IS, Pariiskii GB. J. Chem. Soc. Perkin Trans. 2 2002; 1359.
- 43 Gabr I, Symons MCR. J. Chem. Soc. Faraday Trans. 1996; 92(10): 1767.
- 44 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson BG, Chen M, Wong W, Andres JL, Head-Gordon M, Replogle ES and Pople JA. Gaussian 98. Pittsburgh, PA, Gaussian Inc., 1998.
- 45 Greatorex D, Kemp J. J. Chem. Soc. Faraday Trans. 1972; 68(1): 121.
- 46 Suzuki H, Iwaya M, Mori T. Tetrahedron Lett. 1997; 38(32): 5647.
- 47 Bellamy LJ. The Infra-red Spectra of Complex Molecules. Methuen: London, 1957.
- 48 Bosch E, Kochi JK. J. Org. Chem. 1994; 59(12): 3314.
- 49 Bockman TM, Karpinski ZJ, Sankararaman S, Kochi JK. J. Am. Chem. Soc. 1992; 114(6): 1970.
