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Quantum chemical study of the reaction of ethylene carbonate with methanol associates

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Abstract

Quantum chemical study of the reaction of ethylene carbonate with methanol associates at the B3LYP/6-311++G(df,p) level of theory revealed two probable mechanisms. The one-step mechanism involves SN2 substitution at the sp 2-hybridized carbonyl carbon atom, while the two-step mechanism implies nucleophilic addition to the carbonyl group with formation of tetrahedral intermediate and subsequent elimination. All the examined reactions go through asymmetric concerted transition states.

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References

  1. Aricò, F. and Tundo, P., Russ. Chem. Rev., 2010, vol. 79, no. 6, p. 479.

    Article  Google Scholar 

  2. Żukowska, G.Z., Marcinek, M., Drzewiecki, S., Kryczka, J., Syzdek, J., Adamczyk-Woźniak, A., Wieczorek, W., and Sporzyński, A., J. Power Sources, 2010, vol. 195, p. 7506.

    Article  Google Scholar 

  3. Chang, Y.-M. and Shu, C.-M., J. Therm. Anal. Calorim., 2008, vol. 93, p. 135.

    Article  CAS  Google Scholar 

  4. Wen, L., Xin, C.-Y., and Yang, S.-C., Appl. Energy, 2010, vol. 87, p. 115.

    Article  CAS  Google Scholar 

  5. Pacheco, M. and Marshall, C., Energy Fuels, 1997, vol. 11, p. 2.

    Article  CAS  Google Scholar 

  6. Selva, M., Pure Appl. Chem., 2007, vol. 79, p. 1855.

    Article  CAS  Google Scholar 

  7. Zhao, T., Han, Y., and Sun, Y., Fuel Process. Technol., 2000, vol. 62, p. 187.

    Article  CAS  Google Scholar 

  8. Ren, J., Liu, S., Li, Z., and Xie, K., Catal. Commun., 2011, vol. 12, p. 357.

    Article  CAS  Google Scholar 

  9. Wang, M., Wang, H., Zhao, N., Wei, W., and Sun, Y., Ind. Eng. Chem. Res., 2007, vol. 46, p. 2683.

    Article  CAS  Google Scholar 

  10. Wang, M., Zhao, N., Wei, W., and Sun, Y., Ind. Eng. Chem. Res., 2005, vol. 44, p. 7596.

    Article  CAS  Google Scholar 

  11. Zhang, J., Wang, F., Wei, W., Xiao, F., and Sun, Y., Korean J. Chem. Eng., 2010, vol. 27, p. 1744.

    Article  CAS  Google Scholar 

  12. Wang, J.-Q., Sun, J., Cheng, W.-G., Shi, C.-Y., Dong, K., Zhang, X.-P., and Zhang, S.-J., Catal. Sci. Technol., 2012, vol. 2, p. 600.

    Article  CAS  Google Scholar 

  13. Sankar, M., Madhavan Nair, C., Murty, K.V.G.K., and Manikandan, P., Appl. Catal., A, 2006, vol. 312, p. 108.

    Article  CAS  Google Scholar 

  14. Bhanage, B.M., Fujita, S., Ikushima, Y., and Arai, M., Green Chem., 2003, vol. 5, p. 429.

    Article  CAS  Google Scholar 

  15. Selva, M., Fabris, M., Lucchini, V., Perosa, A., and Noe, M., Org. Biomol. Chem., 2010, vol. 8, p. 5187.

    Article  CAS  Google Scholar 

  16. Soo’s, L., Dea’k, GY., Ke’ki, S., and Zsuga, M., J. Polymer. Sci., Part A: Polym. Chem., 1999, vol. 37, p. 545.

    Article  Google Scholar 

  17. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J. Gaussian 09, Wallingford CT: Gaussian, 2009.

    Google Scholar 

  18. Bushuev, Yu.G. and Dubinkina, T.A., Zh. Fiz. Khim., 1996, vol. 70, p. 1628.

    Google Scholar 

  19. Samuilov, A.Ya., Zenitova, L.A., Samuilov, Ya.D., and Konovalov, A.I., Russ. J. Org. Chem., 2008, vol. 44, p. 1316.

    Article  CAS  Google Scholar 

  20. Samuilov, A.Ya., Zenitova, L.A., Levin, Ya.A., Kurdyukov, A.I., and Samuilov, Ya.D., Russ. J. Phys. Chem. A, 2008, vol. 82, p. 1999.

    Article  CAS  Google Scholar 

  21. Samuilov, A.Ya., Zenitova, L.A., Samuilov, Ya.D., and Konovalov, A.I., Russ. J. Org. Chem., 2009, vol. 45, p. 68.

    Article  CAS  Google Scholar 

  22. Samuilov, A.Ya., Kamalov, T.A., Balabanova, F.B., Samuilov, Ya.D., and Konovalov, A.I., Russ. J. Org. Chem., 2010, vol. 46, p. 1452.

    Article  CAS  Google Scholar 

  23. Samuilov, A.Ya., Kamalov, T.A., Balabanova, F.B., Samuilov, Ya.D., and Konovalov, A.I., Russ. J. Org. Chem., 2012, vol. 48, p. 158.

    Article  CAS  Google Scholar 

  24. Samuilov, A.Ya., Balabanova, F.B., Samuilov, Ya.D., and Konovalov, A.I., Russ. J. Org. Chem., 2012, vol. 48, p. 164.

    Article  CAS  Google Scholar 

  25. Samuilov, A.Ya., Balabanova, F.B., Samuilov, Ya.D., and Konovalov, A.I., Russ. J. Org. Chem., 2012, vol. 48, p. 1512.

    Article  CAS  Google Scholar 

  26. Samuilov, A.Ya., Balabanova, F.B., Valeev, A.R., Samuilov, Ya.D., and Konovalov, A.I., Russ. J. Org. Chem., 2013, vol. 49, p. 28.

    Article  CAS  Google Scholar 

  27. Samuilov, A.Ya., Valeev, A.R., Balabanova, F.B., Samuilov, Ya.D., and Konovalov, A.I., Russ. J. Org. Chem., 2013, vol. 49, p. 1723.

    Article  CAS  Google Scholar 

  28. Katon, J.F. and Conen, M.D., Can. J. Chem., 1975, vol. 53, p. 1378.

    Article  CAS  Google Scholar 

  29. Gontrani, L., Russina, O., Marincola, F.C., and Caminiti, R., J. Chem. Phys., 2009, vol. 31, no. 244 503.

    Google Scholar 

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Authors and Affiliations

  1. Kazan National Research Technological University, ul. K. Marksa 68, Kazan, 420015, Tatarstan, Russia

    A. Ya. Samuilov, F. B. Balabanova, A. R. Valeev & Ya. D. Samuilov

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia

    A. I. Konovalov

Authors
  1. A. Ya. Samuilov
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  2. F. B. Balabanova
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  3. A. R. Valeev
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  4. Ya. D. Samuilov
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  5. A. I. Konovalov
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Correspondence to A. Ya. Samuilov.

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Original Russian Text © A.Ya. Samuilov, F.B. Balabanova, A.R. Valeev, Ya.D. Samuilov, A.I. Konovalov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 12, pp. 1757–1764.

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Samuilov, A.Y., Balabanova, F.B., Valeev, A.R. et al. Quantum chemical study of the reaction of ethylene carbonate with methanol associates. Russ J Org Chem 50, 1738–1745 (2014). https://doi.org/10.1134/S1070428014120033

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  • DOI: https://doi.org/10.1134/S1070428014120033

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