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New Reaction of Dimethylformamide with Acrylic Acid

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Abstract

A new homogeneous reaction of dimethylformamide (DMF) with acrylic acid was studied. The reaction afforded previously unknown 3-[2-carboxyethyl(dimethyl)azaniumyl]propanoate and carbon monoxide. The product structure was determined by 1H and 13C NMR spectroscopy, X-ray diffraction, and elemental analysis, and evolution of gaseous carbon monoxide was confirmed by GC/MS. The kinetic parameters of the described reaction and its overall order were determined.

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References

  1. Chen, X., Xin, Y., Yu, F., and Lan, Z., J. Surfactants Deterg., 2017, vol. 20, p. 1121. https://doi.org/10.1007/s11743-017-1987-z

    Article  CAS  Google Scholar 

  2. Chen, Sh., Chen, Sh., Jiang, S., Mo, Y., Tang, J., and Ge, Z., Surf. Sci., 2011, vol. 605, p. 25. https://doi.org/10.1016/j.susc.2011.03.013

    Article  Google Scholar 

  3. Li, L., Zhao, Y., Zhou, H., Ning, A., Zhang, F., and Zhao (Kent), Z., Tetrahedron Lett., 2017, vol. 58, p. 321. https://doi.org/10.1016/j.tetlet.2016.12.021

    Article  CAS  Google Scholar 

  4. Zhang, S., Yang, X., Tang, B., Yuan, L., Wang, K., Liu, X., Zhu, X., Li, J., Ge, Z., and Chen, S., Chem. Eng. J., 2018, vol. 336, p. 123. https://doi.org/10.1016/j.cej.2017.10.168

    Article  CAS  Google Scholar 

  5. Cai, C., Li, X., Wang, Y., Liu, M., Shi, X., Xia, J., and Shen, M., Chem. Eng. J., 2019, vol. 362, p. 842. https://doi.org/10.1016/j.cej.2019.01.072

    Article  CAS  Google Scholar 

  6. Zhao, G., Dong, X., and Sun, Y., Langmuir, 2019, vol. 35, p. 1846. doi https://doi.org/10.1021/acs.langmuir.8b01921

    Article  CAS  Google Scholar 

  7. Hussain, S.M.Sh., Kamal, M.Sh., and Fogang, L.T., J. Mol. Liq., 2018, vol. 266, p. 43. https://doi.org/10.1016/j.molliq.2018.06.031

    Article  Google Scholar 

  8. Zhen-Jie, M., Xuesong, D., Zhi-Yan, C., and Bao-Hang, H., ACS Appl. Mater. Interfaces, 2018, vol. 10, p. 41350. https://doi.org/10.1021/acsami.8b14671

    Article  Google Scholar 

  9. Wang, M., Xiao, Y., Lin, L., Zhu, X., Du, L., and Shi, X., Bioconjugate Chem., 2018, vol. 29, p. 1081. https://doi.org/10.1021/acs.bioconjchem.7b00747

    Article  Google Scholar 

  10. Rumyantsev, M.S., Kazantsev, O.A., Rumyantsev, S.A., and Kalagaev, I.Yu., Comput. Theor. Chem., 2018, vol. 1129, p. 16. https://doi.org/10.1016/j.comptc.2018.02.017

    Article  CAS  Google Scholar 

  11. APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A), Bruker Advanced X-ray Solutions, Madison, Wisconsin: Bruker AXS, 2006.

    Google Scholar 

  12. Sheldrick, G.M., SADABS, Program for Empirical X-ray Absorption Correction, Delft: Bruker-Nonius, 2004.

    Google Scholar 

  13. Sheldrick, G.M., SHELXTL, Structure Determination Software Suite, v. 6.1, Madison, Wisconsin: Bruker AXS, 2000.

    Google Scholar 

  14. Farrugia, L.J., J. Appl. Crystallogr., 1999, vol. 32, p. 837. https://doi.org/10.1107/S0021889899006020

    Article  CAS  Google Scholar 

  15. Spek, A.L., J. Appl. Crystallogr., 2003, vol. 36, p. 7. https://doi.org/10.1107/S0021889802022112

    Article  CAS  Google Scholar 

  16. Macrae, C.F., Edgington, P.R., McCabe, P., Pidcock, E., Shields, G.P., Taylor, R., Towler, M., and van de Streek, J., J. Appl. Crystallogr., 2006, vol. 39, p. 453. https://doi.org/10.1107/S002188980600731X

    Article  CAS  Google Scholar 

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Correspondence to A. G. Akhmadullina.

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The authors declare the absence of conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 12, pp. 1870–1876.

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Akhmadullina, A.G., Akhmadullin, R.M., Gazizov, A.S. et al. New Reaction of Dimethylformamide with Acrylic Acid. Russ J Org Chem 55, 1864–1868 (2019). https://doi.org/10.1134/S107042801912008X

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  • DOI: https://doi.org/10.1134/S107042801912008X

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