Theoretical enthalpies of formation and structural characterisation of halogenated nitromethanes and isomeric halomethyl nitrites

[1] Asatryan, R., Bozzelli, J. W., & Simmie, J. M. (2008). Thermochemistry of methyl and ethyl nitro, RNO2, and nitrite, RONO, organic compounds. Journal of Physical Chemistry A, 112, 3172–3185. DOI: 10.1021/jp710960u. http://dx.doi.org/10.1021/jp710960u10.1021/jp710960uSearch in Google Scholar

[2] Barss, W. M. (1957). Structure of gaseous chloropicrin as determined by electron diffraction. Journal of Chemical Physics, 27, 1260–1267. DOI: 10.1063/1.1743987. http://dx.doi.org/10.1063/1.174398710.1063/1.1743987Search in Google Scholar

[3] Bergner, A., Dolg, M., Küchle, W., Stoll, H., & Preuss, H. (1993). Ab initio energy-adjusted pseudopotentials for elements of groups 13–17. Molecular Physics, 80, 1431–1441. DOI: 10.1080/00268979300103121. http://dx.doi.org/10.1080/0026897930010312110.1080/00268979300103121Search in Google Scholar

[4] Bull, J. N., Maclagan, R. G. A. R., & Harland, P. W. (2010). On the electron affinity of nitromethane (CH3NO2). Journal of Physical Chemistry A, 114, 3622–3629. DOI: 10.1021/jp9113317. http://dx.doi.org/10.1021/jp911331710.1021/jp9113317Search in Google Scholar

[5] Cox, A. P., & Waring, S. (1972). Microwave spectrum and structure of nitromethane. Journal of Chemical Society Faraday Transactions 2,68, 1060–1071. DOI: 10.1039/f29726801060. 10.1039/f29726801060Search in Google Scholar

[6] Curtiss, L. A., Raghavachari, K., & Pople, J. A. (1993). Gaussian-2 theory using reduced Møller-Plesset orders. Journal of Chemical Physics, 98, 1293–1298, DOI: 10.1063/1.464297. http://dx.doi.org/10.1063/1.46429710.1063/1.464297Search in Google Scholar

[7] Dean, A. M., & Bozzelli, J. W. (1999). Combustion chemistry of nitrogen. In W. C. Gardiner, Jr. (Ed.), Gas-phase combustion chemistry (pp. 125–342). New York, NY, USA: Springer. Search in Google Scholar

[8] Denis, P. A., Ventura, O. N., Le, H. T., & Nguyen, M. T. (2003). Density functional study of the decomposition pathways of nitroethane and 2-nitropropane. Physical Chemistry Chemical Physics, 5, 1730–1738. DOI: 10.1039/b300275f. http://dx.doi.org/10.1039/b300275f10.1039/b300275fSearch in Google Scholar

[9] Foresman, J. B., & Frisch, A. (1996). Exploring chemistry with electronic structure methods (2nd ed.). Pittsburgh, PA, USA: Gaussian Inc. Search in Google Scholar

[10] Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, K. R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Bakken, V., Adamo, V. C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavashari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., 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., Chen, W., Wong, J. L., Gonzalez, C., & Pople, J. (2004). Gaussian 03 [computer software]. Wallingford, CT, USA: Gaussian Inc. Search in Google Scholar

[11] Harland, P. W., & Brooks, P. R. (2010). Crossed-beam studies of electron transfer to oriented trichloronitromethane, CCl3NO2, molecules. Journal of Chemical Physics, 132, 044307. DOI: 10.1063/1.3299280. http://dx.doi.org/10.1063/1.329928010.1063/1.3299280Search in Google Scholar

[12] Jursic, B. S. (1997). Computation of geometries and frequencies of singlet and triplet nitromethane with density functional theory using Gaussian-type orbitals. International Journal of Quantum Chemistry, 64, 263–269. DOI: 10.1002/(SICI)1097-461X(1997)64:2<263::AID-QUA15>3.0.CO;2-A. http://dx.doi.org/10.1002/(SICI)1097-461X(1997)64:2<263::AID-QUA15>3.0.CO;2-A10.1002/(SICI)1097-461X(1997)64:2<263::AID-QUA15>3.0.CO;2-ASearch in Google Scholar

[13] Kirkham Cole, S., Cooper, W. J., Fox, R. V., Gardinali, P. R., Mezyk, S. P., Mincher, B. J., & O’shea, K. E. (2007). Free radical chemistry of disinfection byproducts. 2. Rate constants and degradation mechanisms of trichloronitromethane (Chloropicrin). Environmental Science & Technology, 41, 863–869. DOI: 10.1021/es061410b. http://dx.doi.org/10.1021/es061410b10.1021/es061410bSearch in Google Scholar

[14] Krasner, S. W., Weinberg, H. S., Richardson, S. D., Pastor, S. J., Chinn, R., Sclimenti, N. I., Onstad, G. D., & Thurston, A. D., Jr. (2006). Occurrence of a new generation of disinfection byproducts. Environmntal Science & Technology, 40, 7175–7185. DOI: 10.1021/es060353j. http://dx.doi.org/10.1021/es060353j10.1021/es060353jSearch in Google Scholar

[15] Lu, N., & Thrasher, J. S. (2002). The direct synthesis of trifluoronitromethane, CF3NO2. Journal of Fluorine Chemistry, 117, 181–184. DOI: 10.1016/s0022-1139(02)00183-5. http://dx.doi.org/10.1016/S0022-1139(02)00183-510.1016/S0022-1139(02)00183-5Search in Google Scholar

[16] Luo, Y. R. (2003). Handbook of bond dissociation energies in inorganic compounds. Boca Raton, FL, USA: CRC Press. Search in Google Scholar

[17] Marshall, P., Srinivas, G. N., & Schwartz, M. (2005). A computational study of the thermochemistry of bromine- and iodine-containing methanes and methyl radicals. Journal of Physical Chemistry A, 109, 6371–6379. DOI: 10.1021/jp0518052. http://dx.doi.org/10.1021/jp051805210.1021/jp0518052Search in Google Scholar

[18] Mezyk, S. P., Helgeson, T., Kirkham Cole, S., Cooper, W. J., Fox, R. V., Gardinali, P. R., & Mincher, B. J. (2006). Free radical chemistry of disinfection-byproducts. 1. Kinetics of hydrated electron and hydroxyl radical reactions with halonitromethanes in water. Journal of Physical Chemistry A, 110, 2176–2180. DOI: 10.1021/jp054962+. http://dx.doi.org/10.1021/jp054962+10.1021/jp054962+Search in Google Scholar

[19] Mincher, B. J., Mezyk, S. P., Cooper, W. J., Kirkham Cole, S., Fox, R. V., & Gardinali, P. R., (2010). Free radical chemistry of disinfection-byproducts. 3. Degradation mechanisms of chloronitromethane, bromonitromethane, and dichloronitromethane. Journal of Physical Chemistry A, 114, 117–125. DOI: 10.1021/jp907305g. http://dx.doi.org/10.1021/jp907305g10.1021/jp907305gSearch in Google Scholar

[20] Munakata, H., Kakumoto, T., & Baker, J. (1997). An MP2 and density functional study of the oxides of nitrogen. Journal of Molecular Structure: THEOCHEM, 391, 231–240. DOI: 10.1016/s0166-1280(96)04788-4. http://dx.doi.org/10.1016/S0166-1280(96)04788-410.1016/S0166-1280(96)04788-4Search in Google Scholar

[21] Pagsberg, P., Jodkowski, J. T., Ratajczak, E., & Sillesen, A. (1998). Experimental and theoretical studies of the reaction between CF3 and NO2 at 298 K. Chemical Physics Letters, 286, 138–144, DOI: 10.1016/s0009-2614(98)00074-8. http://dx.doi.org/10.1016/S0009-2614(98)00074-810.1016/S0009-2614(98)00074-8Search in Google Scholar

[22] Pauling, L. (1932). The nature of the chemical bond. IV. The energy of single bonds and the relative electronegativity of atoms. Journal of the American Chemical Society, 54, 3570–3582. DOI: 10.1021/ja01348a011. http://dx.doi.org/10.1021/ja01348a01110.1021/ja01348a011Search in Google Scholar

[23] Plewa, M. J., Wagner, E. D., Jazwierska, P., Richardson, S. D., Chen, P. H., & McKague, A. B. (2004). Halonitromethane drinking water disinfection byproducts: Chemical characterization and mammalian cell cytotoxicity and genotoxicity. Environmental Science & Technology, 38, 62–68. DOI: 10.1021/es030477l. http://dx.doi.org/10.1021/es030477l10.1021/es030477lSearch in Google Scholar PubMed

[24] Riad Manaa, M., & Fried, L. E. (1998). DFT and ab initio study of the unimolecular decomposition of the lowest singlet and triplet states of nitromethane. Journal of Physical Chemistry A, 102, 9884–9889. DOI: 10.1021/jp982003s. http://dx.doi.org/10.1021/jp982003s10.1021/jp982003sSearch in Google Scholar

[25] Richardson, S. D. (2003). Water analysis: Emerging contaminants and current issues. Analytical Chemistry, 75, 2831–2857. DOI: 10.1021/ac0301301. http://dx.doi.org/10.1021/ac030130110.1021/ac0301301Search in Google Scholar

[26] Rosenberg, M., & Sølling, T. I. (2010). Computational investigation of photo induced processes in alkyl nitrites and the product alkoxy radicals. Chemical Physics Letters, 484, 113–118, DOI: 10.1016/j.cplett.2009.11.001. http://dx.doi.org/10.1016/j.cplett.2009.11.00110.1016/j.cplett.2009.11.001Search in Google Scholar

[27] Sander, S. P., Golden, D. M., Kurylo, M. J., Moortgat, G. K., Wine, P. H., Ravishankara, A. R., Kolb, C. E., Molina, M. J., Finlayson-Pitts, B. J., Huie, R. E., & Orkin, V. L. (2006). Chemical kinetics and photochemical data for use in Atmospheric Studies Evaluation Number 15. Pasadena, CA, USA: Jet Propulsion Laboratory, National Aeronautics and Space Administration. (JPL Publication 06-2) Search in Google Scholar

[28] Schwartz, M., Peebles, L. R., Berry, R. J., & Marshall, P. (2003). A computational study of chlorofluoro-methyl radicals. Journal of Chemical Physics, 118, 557–565. DOI: 10.1063/1.1524157. http://dx.doi.org/10.1063/1.152415710.1063/1.1524157Search in Google Scholar

[29] Shao, J. X., Cheng, X. L., & Yang, X. D. (2005). Calculations of the bond dissociation energies for NO2 scission in some nitro compounds. Structural Chemistry, 16, 457–460. DOI: 10.1007/s11224-005-4334-3. http://dx.doi.org/10.1007/s11224-005-4334-310.1007/s11224-005-4334-3Search in Google Scholar

[30] Shen, Q., Brown, J. W., Malona, J. A., Cochran, J. C., & Richardson, A. D. (2006). Molecular structure and conformation of chloronitromethane as determined by gas-phase electron diffraction and theoretical calculations. Journal of Physical Chemistry A, 110, 7491–7495. DOI: 10.1021/jp061100f. http://dx.doi.org/10.1021/jp061100f10.1021/jp061100fSearch in Google Scholar

[31] Temussi, P. A., & Tancredi, T. (1968). The mechanism of isomerization of methyl nitrite. Journal of Physical Chemistry, 72, 3581–3583. DOI: 10.1021/j100856a039. http://dx.doi.org/10.1021/j100856a03910.1021/j100856a039Search in Google Scholar

[32] Turner, P. H., Corkill, M. J., & Cox, A. P. (1979). Microwave spectra and structures of cis- and transmethyl nitrite. Methyl barrier in trans-methyl nitrite. Journal of Physical Chemistry, 83, 1473–1482. DOI: 10.1021/j100474a023. 10.1021/j100474a023Search in Google Scholar

[33] Ventura, O. N., Saenz-Méndez, P., & Bottinelli, F. (2011). Computational study on the partial dechlorination of the pesticide chloropicrin by sulfur species. Theoretical Chemistry Accounts, 130, 955–963. DOI: 10.1007/s00214-011-1057-y. http://dx.doi.org/10.1007/s00214-011-1057-y10.1007/s00214-011-1057-ySearch in Google Scholar

[34] Wade, E. A., Reak, K. E., Parsons, B. F., Clemes, T. P., & Singmaster, K. A. (2002). Photochemistry of chloropicrin in cryogenic matrices. Chemical Physics Letters, 365, 473–479. DOI: 10.1016/s0009-2614(02)01495-1. http://dx.doi.org/10.1016/S0009-2614(02)01495-110.1016/S0009-2614(02)01495-1Search in Google Scholar

[35] Wadt, W. R., & Hay, P. J. (1985). Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi. Journal of Chemical Physics, 82, 284–298. DOI: 10.1063/1.448800. http://dx.doi.org/10.1063/1.44880010.1063/1.448800Search in Google Scholar

[36] Zhu, R. S., & Lin, M. C. (2009). CH3NO2 decomposition/isomerization mechanism and product branching ratios: An ab initio chemical kinetic study. Chemical Physics Letters, 478, 11–16. DOI: 10.1016/j.cplett.2009.07.034. http://dx.doi.org/10.1016/j.cplett.2009.07.03410.1016/j.cplett.2009.07.034Search in Google Scholar