The possibility of a two-step oxidation of the surface of C20 fullerene by a single molecule of nitric (V) acid

Document Type : Research Article

Authors

1 Department of Chemistry, Qaemshahr Branch, IslamicAzadUniversity, Qaemshahr, Iran

2 Institute of Organic Chemistry and Technology, Cracow University of Technology, Cracow, Poland

3 Department of EnvironmentalHealth, Faculty of Health, Mazandaran University of Medical Sciences, Sari, Iran

Abstract

< p>Oxidation of fullerenes, carbon nanotubes, and graphene, is one of the first proposed and successful approaches for further functionalization of these nano dimension carbon allotropes. Also, the C20 fullerene, as the smallest known carbon cage, is one of the most important species, in the future of nanotechnology. In this regard, the potential energy surface (PES) study suggests that reaction between nitric (V) acid and C20 fullerene, first leads to the production of a relatively meta-stable kinetically allowed intermediate via a [2+3] cycloaddition. After the intermediate is produced, it would subsequently be decomposed to a C20O open-shell fullerene and a HNO2molecule. Such oxidations were observed via the reaction between strong acids and some of the nano-sized carbon allotropes like carbon nanotube CNTs or spherical fullerenes. The results showed that the produced intermediate directly changes to the final product of oxidation, in a fast process.

Keywords

References

[1] N. Levy, J.D Rose, The aliphatic nitro-compounds, Chem. Soc. 1 (1947) 358-395.
[2] G. Klopman, H.S. Rosenkranz, Structural basis of carcinogenicity in rodents of genotoxicants and non-genotoxicants, Mutat. Res. Fundam. Mol. Mech. Mutagen.126 (1984) 227-238.
[3] L.R. Maxwell, V.M. Mosley, Molecular structure of nitrogen dioxide and nitric acid by electron diffraction, J. Chem. Phys.8 (1940) 738-742.
[4] J.H. Boyer, B.G.K. Torssell, G.A. Olah, R. Malhotra, S.C. Narong, Organic Nitro Chemistry Series, 2001.
[5] a) R. Jasiński, In the searching for zwitterionic intermediates on reaction paths of [3+2] cycloaddition reactions between 2, 2, 4, 4-tetramethyl-3-thiocyclobutanone S-methylide and polymerizable olefins. RSC. Adv. 122 (2015) 101045-101048;
b) R. Jasiński, E. Jasińska, E. Dresler, A DFT computational study of the molecular mechanism of [3+ 2] cycloaddition reactions between nitroethene and benzonitrile N-oxides, J. Mol. Model.  23 (2017) 1-13.
[6] R. Ballini, N. Araújo, M.V. Gil, E. Román, J.A. Serrano, Conjugated Nitrodienes. Synthesis and Reactivity, Chem. Rev.113 (2013) 3493-3515.
[7] R. Huisgen,1, 3‐dipolar cycloadditions. Past and future,Angew. Chem. Int. Ed2(1963) 565-598.
[8] P. Perez, L.R. Domingo, A. Aizman, R. Contreras, Quantitative characterization of the global electrophilicity pattern
of some reagents involved in 1, 3-dipolar cycloaddition reactions,Theory.Comput. Chem.19 (2007) 139-201.
[9] P. Pérez, L.R. Domingo, M.J. Aurell, R. Contreras,  Quantitative characterization of the global electrophilicity pattern of some reagents involved in 1,3-dipolar cycloaddition reactions,Tetrahedron59 (2003) 3117-3125.
[10] R. Jasiński, 1,3-Dipolar cycloaddition reactions: mechanistic aspects and application in organic synthesis, RTN, Radom, 2015.
[11] S.A. Bakunov, S.M. Bakunova, T. Wenzler, M. Ghebru, K.A. Werbovetz, R. Brun, R.R. Tidwell, Synthesis and
antiprotozoal activity of cationic 1,4-diphenyl-1 H-1, 2,3-triazoles, J. Med. Chem.53 (2009) 254-272.
[12] Z. Zeng, R. Wang, B. Twamley, D.A. Parrish, J.N.M. Shreeve, Polyamino-Substituted Guanyl-Triazole Dinitramide Salts with Extensive Hydrogen Bonding: Synthesis and Properties as New Energetic Materials, Chem. Mater.20 (2008) 6176-6182.
[13] Y. Kanbur, Z. Küçükyavuz, Synthesis and characterization of surface modified fullerene, Fuller. Nanotub. Car. N. 20 (2012) 119-126.
[14] F. Avilés, J.V. Cauich-Rodríguez, L. Moo-Tah, A. May-Pat, R. Vargas-Coronado, Evaluation of mild acid oxidation treatments for MWCNT functionalization, Carbon 47 (2009) 2970-2975.
[15] a) E. Vessally, S.A. Siadati, A. Hosseinian, L. Edjlali, Selective sensing of ozone and the chemically active gaseous species of the troposphere by using the C20 fullerene and graphene segment, Talanta 162 (2017) 505-510;
b) S.A. Siadati, E. Vessally, A. Hosseinian, L. Edjlali,Possibility of sensing, adsorbing, and destructing the Tabun-2D-skeletal (Tabun nerve agent) by C20 fullerene and its boron and nitrogen doped derivatives, Syn. Met. 220 (2016) 606-611;
c) S.A. Siadati, A Theoretical Study on the Possibility of Functionalization of C20 Fullerene via its Diels-Alder Reaction with 1, 3-Butadiene, Lett. Org. Chem.13 (2016) 2-6;
d) S.A. Siadati, N. Navabeh, Investigation of the possibility of functionalization of C20 fullerene by benzene via Diels–Alder reaction, Physica E: Low-dimens. Syst. 84 (2016) 55-59.
[16] a) S.A. Siadati, M.S. Amini-Fazl, E. Babanezhad, The possibility of sensing and inactivating the hazardous air pollutant species via adsorption and their [2+3] cycloaddition reactions with C 20 fullerene, Sens.Actuat. B Chem. 237 (2016) 591-596;
b) S.A. Siadati, A. Mirabi, Diels–Alder versus 1, 3-dipolar cycloaddition pathways in the reaction of C20 fullerene and 2-furan nitrile oxide, Prog. React. Kin. Mech. 40 (2015) 383-390;
c) P. Pakravan, S.A. Siadati, The possibility of using C20 fullerene and graphene as semiconductor segments for detection, and destruction of cyanogen-chloride chemical agent, J Mol. Graph. Model. 75 (2017) 80-84.
[17] M.T. Baei,Diels–Alder versus 1, 3-dipolar cycloaddition pathways in the reaction of C20 fullerene and 2-furan nitrile oxide,Heteroatom. Chem. 24 (2013) 516-523.
[18] S. Dasgupta, B. Torok, Environmentally benign synthesis of heterocyclic compounds by combined microwave-assisted heterogeneous catalytic approaches, Org. Prep. Proced. Int.40 (2008) 1-65.
[19]A.S. Chhatre,R.A. Joshi,B.D. Kulkarni, Microemulsions as media for organic synthesis: selective nitration of phenol to ortho-nitrophenol using dilute nitric acid,J. Colloid Interface Sci.158 (1993) 183-187.
[20] Y.P. An, C.L. Yang, M.S. Wang, X.G. Ma, D.H. Wang,First-principles study of structure and quantum transport properties of C20 fullerene,J Chem. Phys. 131 (2009) 24311.
[21] Frisch, M. J. et al. Gaussian 03, Revision B.04 Gaussian: Pittsburgh PA, 2003.
[22] A.D. Becke,Density-functional exchange-energy approximation with correct asymptotic behavior,Phys. Rev.A38 (1988) 3098-3100.
[23] C. Lee,W. Yang,R.G. Parr,Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,Phys. Rev. B371 (1988) 785-789.
[24] V.B. Delchev,M.V. Nenkova,Theoretical modeling of the ground state intramolecular proton transfer in cytosine: DFT level study,Acta.Chim.Slov.55 (2008) 132-137.
[25] R. Jasiński,On the question of zwitterionic intermediates in 1, 3-dipolar cycloadditions between hexafluoroacetone and sterically crowded diazocompounds,J Fluor. Chem.176 (2015) 35-39.
[26] R. Jasiński,Nitroacetylene as dipolarophile in [2+ 3] cycloaddition reactions with allenyl-type three-atom components: DFT computational study,Monatsh. Chem.146 (2015) 591-599.
[27] R. Jasiński,M. Ziółkowska,O.M. Demchuk,A. Maziarka,Regio-and stereoselectivity of polar [2+ 3] cycloaddition reactions between (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone and selected (E)-2-substituted nitroethenes,Central Eur. J Chem.12 (2014) 586-593.
[28] C. Peng, P.Y. Ayala, H.B. Schlegel,M.J. Frisch,Using redundant internal coordinates to optimize equilibrium geometries and transition states,J Comput. Chem.17 (1996) 49-56.
[29] C. Peng,H.B. Schlegel, Combining synchronous transit and quasi-newton methods to find transition states,Isr. J Chem.33 (1996) 449-454.
[30] C. Gonzalez,H.B. Schlegel,An improved algorithm for reaction path following,J Chem. Phys.90 (1989) 2154-2162.
[31] C. Gonzalez,H.B. Schlegel,the Atoms Boron through Neon and Hydrogen,J Phys. Chem. 94 (1990) 5523-5527.
[32] A.E. Reed,L.A. Curtiss,F. Weinhold, Inter molecular Interactions from a Natural Bond Orbital, Donor- Acceptor Viewpoint,Chem.Rev.88 (1988) 899-926.
[33] J.E. Carpenter,F.J. Weinhold,Analysis of the geometry of the hydroxyl methyl radical by the “different hybrids for different spins” natural bond orbital procedure, J Mol. Struct. (Theochem)169 (1988) 41-62.
 [34] L. Pauling, Atomic Radii and Interatomic Distances in Metals, J Am. Chem. Soc.69 (1947) 542-545.
[35] L.R. Domingo, A new C–C bond formation model based on the quantum chemical topology of electron density, RSC Adv. 4 (2014) 32415-32428.
[36] V. Barone, M. Cossi, Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model, J Phys. Chem. A 102 (1998) 1995-2001.
[37] S.A. Lopez, M.E. Munk, K.N. Houk, Mechanisms and transition states of 1, 3-dipolar cycloadditions of phenyl azide with enamines: a computational analysis, J Org. Chem. 78 (2013) 1576-1582.
[38] S.A. Siadati, Beyond the alternatives that switch the mechanism of the 1, 3-dipolar cycloadditions from concerted to stepwise or vice versa: a literature review, Prog. React. Kinet. Mech. 41 (2016) 331-344.
[39] S.A. Siadati, An example of a stepwise mechanism for the catalyst-free 1, 3-dipolar cycloaddition between a nitrile oxide and an electron rich alkene, Tetrahedron Lett.56 (2015) 4857-4863.
[40] R. Jasiński, In the searching for zwitterionic intermediates on reaction paths of [3+ 2] cycloaddition reactions between 2, 2, 4, 4-tetramethyl-3-thiocyclobutanone S-methylide and polymerizable olefin, RSC. Adv., 5 (2015) 101045-101048.
[41] B. Mohtat, S.A. Siadati, M.A. Khalilzadeh, D. Zareyee, The concern of emergence of multi-station reaction pathways that might make stepwise the mechanism of the 1, 3-dipolar cycloadditions of azides and alkynes, J Mol. Struct. 1155 (2018) 58-64.
 
 
 
 
 
 
 

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History

  • Receive Date: 24 January 2019
  • Revise Date: 14 February 2019
  • Accept Date: 20 February 2019

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