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Conformational Analysis of Dibutylphosphorylacetic Acid N,N-Dibutylamide in Solution

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Abstract

Polarity of N,N-dibutylamide of dibutylphosphorylacetic acid has been determined and its conformational analysis has been carried out by the methods of dipole moments and quantum chemistry [DFT B3PW91/6-311++G(df,p)+CPCM]. In solution, this acetamide exists as conformational equilibrium of several forms with staggered gauche- and trans-orientations of the substituents relative to the P=O bond, in which intramolecular contacts are formed involving hydrogen atoms of butyl substituents at the nitrogen atom and the oxygen atom of the P=O group.

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REFERENCES

  1. Horwitz, E.P. and Schulz, W.W., The Truex Process: A Vital Tool for Disposal of U.S. Defense Nuclear Waste, in New Separation Chemistry Techniques for Radioactive Waste and Other Specific Applications, Dordrecht: Springer, 1991, p. 21.

  2. Sharova, E.V., Artyushin, O.I., and Odinets, I.L., Russ. Chem. Rev., 2014, vol. 83, no. 2, p. 95. https://doi.org/10.1070/rc2014v083n02abeh004384

    Article  Google Scholar 

  3. Myasoedov, B.F., Kalmykov, S.N., Kulyako, Y.M., and Vinokurov, S.E., Geochem. Int., 2016, vol. 54, no. 13, p. 1156. https://doi.org/10.1134/S0016702916130115

    Article  CAS  Google Scholar 

  4. Leoncini, A., Huskens, J., and Verboom, W., Chem. Soc. Rev., 2017, vol. 46, no. 23, p. 7229. https://doi.org/10.1039/c7cs00574a

    Article  CAS  PubMed  Google Scholar 

  5. Alyapyshev, M.Y., Babain, V., and Ustynyuk, Y.A., Russ. Chem. Rev., 2016, vol. 85, no. 9, p. 943. https://doi.org/10.1070/rcr4589

    Article  CAS  Google Scholar 

  6. Turanov, A.N., Karandashev, V.K., Artyushin, O.I., Sharova, E.V., and Khvostikov, V.A., Russ. J. Inorg. Chem., 2020, vol. 65, no. 8, p. 1226. https://doi.org/10.1134/S0036023620080185

    Article  Google Scholar 

  7. Turanov, A.N., Karandashev, V.K., Artyushin, O.I., Peregudov, A.S., Khvostikov, V.A., and Bondarenko, N.A., Russ. J. Inorg. Chem., 2020, vol. 65, no. 6, p. 905. https://doi.org/10.1134/s0036023620060248

    Article  CAS  Google Scholar 

  8. Turanov, A.N., Karandashev, V.K., Khvostikov, V.A., Artyushin, O.I., and Bondarenko, N.A., Russ. J. Gen. Chem., 2021, vol. 91, no. 3, p. 383. https://doi.org/10.1134/S1070363221030075

    Article  CAS  Google Scholar 

  9. Turanov, A.N., Karandashev, V.K., and Yarkevich, A.N., Russ. J. Inorg. Chem., 2021, vol. 66, no. 4, p. 572. https://doi.org/10.1134/S0036023621040240

    Article  CAS  Google Scholar 

  10. Werner, E.J. and Biros, S.M., Org. Chem. Front., 2019, vol. 6, no. 12, p. 2067. https://doi.org/10.1039/c9qo00242a

    Article  CAS  Google Scholar 

  11. Turanov, A.N., Karandashev, V.K., Yarkevich, A.N., and Khvostikov, V.A., Radiochemistry, 2019, vol. 61, no. 6, p. 694. https://doi.org/10.1134/s1066362219060092

    Article  CAS  Google Scholar 

  12. Bhattacharyya, A. and Mohapatra, P.K., Radiochim. Acta, 2019, vol. 107, nos. 9–11, p. 931. https://doi.org/10.1515/ract-2018-3064

    Article  CAS  Google Scholar 

  13. Pitchaiah, K.C., Sujatha, K., Rao, C.V.S.B., Subramaniam, S., Sivaraman, N., and Rao, P.R.V., Radiochim. Acta, 2015, vol. 103, no. 4, p. 245. https://doi.org/10.1515/ract-2014-2300

    Article  CAS  Google Scholar 

  14. Sujatha, K., Pitchaiah, K., Sivaraman, N., Nagarajan, K., Srinivasan, T., and Rao, P.V., Desal. Water Treat., 2013, vol. 52, p. 470. https://doi.org/10.1080/19443994.2013.808729

    Article  CAS  Google Scholar 

  15. Annam, S., Rao, C.B., Sivaraman, N., Sivaramakrishna, A., and Vijayakrishna, K., React. Funct. Polym., 2018, vol. 131, p. 203. https://doi.org/10.1016/j.reactfunctpolym.2018.07.026

    Article  CAS  Google Scholar 

  16. Kameník, J., Šebesta, F., John, J., Böhmer, V., Rudzevich, V., and Grüner, B., J. Radioanal. Nucl. Chem., 2015, vol. 304, no. 1, p. 313. https://doi.org/10.1007/s10967-014-3543-x

    Article  CAS  Google Scholar 

  17. Artem’ev, A.V., Berezin, A.S., Brel, V.K., Morgalyuk, V.P., and Samsonenko, D.G., Polyhedron, 2018, vol. 148, no. 1, p. 184. https://doi.org/10.1016/j.poly.2018.04.012

    Article  CAS  Google Scholar 

  18. Vasil’ev, A.A., Aleksenko, V.Y., Aleksanyan, D.V., and Kozlov, V.A., Mendeleev Commun., 2013, vol. 23, no. 6, p. 344. https://doi.org/10.1016/j.mencom.2013.11.014

    Article  CAS  Google Scholar 

  19. Yarkevich, A.N., Brel, V., Makhaeva, G.F., Serebryakova, O.G., Boltneva, N.P., and Kovaleva, N.V., Russ. J. Gen. Chem., 2015, vol. 85, no. 7, p. 1644. https://doi.org/10.1134/s1070363215070129

    Article  CAS  Google Scholar 

  20. Rosario-Amorin, D., Dehaudt, J., Caudle, L.J., Dickie, D., and Paine, R.T., Phosphorus, Sulfur, Silicon, Relat. Elem., 2016, vol., 191, no. 3, p. 520. https://doi.org/10.1080/10426507.2015.1091835

    Article  CAS  Google Scholar 

  21. Sharova, E.V., Artyushin, O.I., Nelyubina, Y.V., Lyssenko, K., Passechnik, M.P., and Odinets, I.L., Russ. Chem. Bull., 2008, vol. 57, no. 9, p. 1890. https://doi.org/10.1007/s11172-008-0255-9

    Article  CAS  Google Scholar 

  22. Caudle, L., Duesler, E., and Paine, R., Inorg. Chim. Acta, 1985, vol. 110, no. 2, p. 91. https://doi.org/10.1016/s0020-1693(00)84562-4

    Article  CAS  Google Scholar 

  23. Caudle, L.J., Duesler, E.N., and Paine, R.T., Inorg. Chem., 1985, vol. 24, p. 4441. https://doi.org/10.1021/ic00219a054

    Article  CAS  Google Scholar 

  24. Aleksenko, V.Yu., Sharova, E.V., Artyushin, O.I., Aleksanyan, D.V., Klemenkova, Z.S., Nelyubina, Yu.V., Petrovskii, P.V., Kozlov, V.A., and Odinets, I.L., Polyhedron, 2013, vol. 51, no. 1, p. 168. https://doi.org/10.1016/j.poly.2012.12.025

    Article  CAS  Google Scholar 

  25. Das, D., Sivaramakrishna, A., Gopakumar, G., Rao, C.B., Sivaraman, N., and Vijayakrishna, K., Polyhedron, 2018, vol. 141, p. 215. https://doi.org/10.1016/j.poly.2017.11.036

    Article  CAS  Google Scholar 

  26. Antipin, M.Y., Struchkov, Y.T., Matrosov, E.I., and Kabachnik, M.I., J. Struct. Chem., 1985, vol. 26, no. 3, p. 441. https://doi.org/10.1007/bf00749385

    Article  Google Scholar 

  27. Yaftian, M., Hassanzadeh, L., Eshraghik, M., and Matt, D., Sep. Purif. Technol., 2003, vol. 31, no. 3, p. 261. https://doi.org/10.1016/S1383-5866(02)00203-4

    Article  CAS  Google Scholar 

  28. Kuznetsova, A.A., Chachkov, D.V., Artyushin, O.I., Bondarenko, N.A., and Vereshchagina, Y.A., Molecules, 2021, vol. 26, no. 16. 4832. https://doi.org/10.3390/molecules26164832

  29. Vereshchagina, Y.A., Khanafieva, R.R., Chachkov, D.V., Artyushin, O.I., Sharova, E.V., and Ishmaeva, E.A., Russ. J. Org. Chem., 2016, vol. 52, no. 10, p. 1413. https://doi.org/10.1134/S1070428016100079

    Article  CAS  Google Scholar 

  30. Shvetsov, I.K., Trukhlyaev, P.S., Kalistratov, V.A., Kulazhko, V.G., Haritonov, A.V., Antoshin, A.E., and Tsvetkov, E.N., Radiokhim., 1989, vol. 3, no. 2, p. 63.

    Google Scholar 

  31. Kem, K.M., Nguyen, N.V., and Cross, D.J., J. Org. Chem., 1981, vol. 46, no. 25, p. 5188. https://doi.org/10.1021/jo00338a025

    Article  CAS  Google Scholar 

  32. Ishmaeva, E.A., Timosheva, A.P., Timosheva, N.V., and Vereshchagina, Ya.A., Spravochnik po dipol’nym momentam fosfororganicheskikh soedinenii (Handbook on Dipole Moments of Organophosphorus Compounds), Kazan: Kazan. Univ., 1998.

  33. Tsvetkov, E.N., Bondarenko, N.A., Malakhova, I.G., and Kabachnik, M.I., Synthesis, 1986, vol. 1986, no. 3, p. 198. https://doi.org/10.1055/s-1986-31510

    Article  Google Scholar 

  34. Osipov, O.A., Minkin, V.I., and Garnovskii, A.D., Spravochnik po dipol’nym momentam (Handbook on Dipole Moments), Moscow: Vysshaya Shkola, 1971.

  35. Ishmaeva, E.A., Zimin, M.G., Galeeva, R.M., and Pudovik, A.N., Russ. Chem. Bull., 1971, vol. 20, no. 3, p. 473. https://doi.org/10.1007/bf00852033

    Article  Google Scholar 

  36. Gribov, L.A. and Popov, E.M., Dokl. Akad. Nauk SSSR, 1962, vol. 145, no. 4, p. 761.

    CAS  Google Scholar 

  37. Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648. https://doi.org/10.1063/1.464913

    Article  CAS  Google Scholar 

  38. Perdew, J.P., Burke, K., and Wang, Y., Phys. Rev. (B), 1996, vol. 54, no. 23, p. 16533. https://doi.org/10.1103/PhysRevB.54.16533

    Article  CAS  Google Scholar 

  39. McLean, A.D. and Chandler, G.S., J. Chem. Phys., 1980, vol. 72, no. 10, p. 5639. https://doi.org/10.1063/1.438980

    Article  CAS  Google Scholar 

  40. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, Jr.J.A., 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, 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., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., 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., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., 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, M.W., Gonzalez, C., and Pople, J.A., Gaussian 09, Pittsburgh PA: Gaussian Inc., 2009.

  41. Cossi, M., Rega, N., Scalmani, G., and Barone, V., J. Comp. Chem., 2003, vol. 24, no. 6, p. 669. https://doi.org/10.1002/jcc.10189

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The calculations were performed at Kazan Department of Joint Supercomputer Center of RAS and at Kazan Federal University.

Funding

This study was financially supported by the Russian Foundation for Basic Research (project no. 20-03-00119) and performed partially with the use of the equipment of the Center for Collective Usage of National Research Center “Kurchatov Institute.”

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Authors and Affiliations

  1. Kazan (Volga Region) Federal University, 420008, Kazan, Russia

    A. A. Kuznetsova & Ya. A. Vereshchagina

  2. Kazan Department of Joint Supercomputer Center of Russian Academy of Sciences – Branch of Federal State Institution “Scientific Research Institute for System Analysis of the Russian Academy of Sciences”, 420111, Kazan, Russia

    D. V. Chachkov

  3. Institute of Chemical Reagents and High Purity Chemical Substances of National Research Centre “Kurchatov Institute”, 107076, Moscow, Russia

    K. V. Tcarkova & N. A. Bondarenko

  4. National Research Centre “Kurchatov Institute”, 123182, Moscow, Russia

    K. V. Tcarkova & N. A. Bondarenko

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  1. A. A. Kuznetsova
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  2. D. V. Chachkov
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Correspondence to Ya. A. Vereshchagina.

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To the 100th Anniversary of M.G. Voronkov

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Kuznetsova, A.A., Chachkov, D.V., Tcarkova, K.V. et al. Conformational Analysis of Dibutylphosphorylacetic Acid N,N-Dibutylamide in Solution. Russ J Gen Chem 91, 2581–2587 (2021). https://doi.org/10.1134/S107036322112029X

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