Abstract
Amidation of diphenylphosphorylacetic acid gave tridentate ligands Ph2P(O)CH2CON(R)· CH2CH2P(O)Ph2 (R = Me, Bu, Oct) containing a phosphoryl group in the amide moiety. According to the 1H, 13C{1H}, and 31P{1H} NMR spectra, the synthesized compounds exist in CDCl3 solution as two conformers at the ratios of ~2.5 : 1 (R = Me), 2.6 : 1 (R = Bu), and 3.0:1 (R = Oct). These ratios do not change with temperature (heating or cooling).
Similar content being viewed by others
REFERENCES
Rozen, A.M. and Krupnov, B.V., Russ. Chem. Rev., 1996, vol. 65, no. 11, p. 973. https://doi.org/10.1070/RC1996v065n11ABEH000241
Mastryukova, T.A., Artyushin, O.I., Odinets, I.L., and Tananaev, I.G., Ross. Khim. Zh., 2005, vol. 49, no. 2, p. 86.
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
Artyushin, O.I., Sharova, E.V., Odinets, I.L., Lysenko, K.A., Golovanov, D.G., Mastryukova, T.A., Pribylova, G.V., Tananaev, I.G., and Myasoedova, G.V., Russ. Chem. Bull., Int. Ed., 2006, vol. 55, no. 8, p. 1440. https://doi.org/10.1007/s11172-006-0437-2
Bondarenko, N.A., Kharlamov, A.V., and Vendilo, A.G., Russ. Chem. Bull., Int. Ed., 2009, vol. 58, no. 9, p. 1872. https://doi.org/10.1007/s11172-009-0256-3
Evreinov, V.I., Safronova, Z.V., Yarkevich, A.N., Kharitonov, A.V., Bondarenko, N.A., and Tsvetkov, E.N., Russ. J. Gen. Chem., 1999, vol. 69, no. 7, p. 1047.
Shvetsov, I.K., Trukhlyaev, P.S., Kalistratov, V.A., Kulazhko, V.G., Kharitonov, A.V., Antoshin, A.E., and Tsvetkov, E.N., Radiokhimiya, 1989, vol. 3, no. 2, p. 63.
Bondarenko, N.A., Russ. J. Gen. Chem., 1999, vol. 69, no. 7, p. 1016.
Turanov, A.N., Karandashev, V.K., Kharitonov, A.V., Lezhnev, A.N., Safronova, Z.V., Yarkevich, A.N., and Tsvetkov, E.N., Russ. J. Gen. Chem., 1999, vol. 69, no. 7, p. 1068.
Rahman, M.S., Steed, J.W., and Hii, R.R., Synthesis, 2000, vol. 2000, no. 9, p. 1320. https://doi.org/10.1055/s-2000-6422
Matveeva, E.V., Petrovskii, P.V., Klemenkova, Z.S., Bondarenko, N.A., and Odinets, I.L., C. R. Chim., 2010, vol. 13, nos. 8–9, p. 964. https://doi.org/10.1016/j.crci.2010.03.005
Yarkevich, A.N., Petrova, L.N., and Bachurin, S.O., Russ. J. Gen. Chem., 2012, vol. 82, no. 10, p 1659. https://doi.org/10.1134/S1070363212100052
Gordon, A.J. and Ford, R.A., The Chemistʼs Companion: A Handbook of Practical Data, Techniques, and References, New York: Wiley, 1972.
Petrov, E.S., Tsvetkov, E.N., Terekhova, M.I., Malevannaya, R.A., Shatenshtein, A.I., and Kabachnik, M.I., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1976, vol. 25, no. 3, p. 517. https://doi.org/10.1007/BF01106644
Bondarenko, N.A., Rudomino, M.V., and Tsvetkov, E.N., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, vol. 39, no. 5, p. 1076. https://doi.org/10.1007/BF00961729
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
ACKNOWLEDGMENTS
This study was supported by the Ministry of Science and Higher Education of the Russian Federation using the facilities of the joint center at the Kurchatov Institute and Center for Molecular Composition Studies at the Nesmeyanov Institute of Organoelement Compounds (Russian Academy of Sciences).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare the absence of conflict of interest.
Rights and permissions
About this article
Cite this article
Bondarenko, N.A., Belus’, S.K., Artyushin, O.I. et al. New Tridentate Carbamoylmethylphosphine Oxides: Synthesis and NMR Spectra. Russ J Gen Chem 90, 2273–2280 (2020). https://doi.org/10.1134/S1070363220120099
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363220120099