Abstract
The stability of S,S-diamino-λ4-sulfanes R2S(NHR′)2 (R = Me, CH2=CHCH2, Ph, CH2=CH, F; R′ = Me, SO2Me, SO2CF3) to decomposition into the sulfimide R2S=NR′ and amine (sulfonamide) R′NH2 was analyzed by MP2/6-311G(d,p) theoretical calculations. Factors stabilizing diamino-λ4-sulfanes with a tetravalent four-coordinate sulfur atom are the high total electronegativity of the R and R′ substituents and the lack of conjugation with the R substituents. The results of calculations are fully consistent with the experimental data.
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References
Michaelis, A., Justus Liebigs Ann. Chem., 1873, vol. 170, p. 1.
Smith, W.C., Tullock, A.W., Muetterties, E.L., Hasek, W.R., Fawcett, F.S., Engelhardt, V.A., and Coffman, D.D., J. Am. Chem. Soc., 1959, vol. 81, p. 3165.
Tullock, A.W., Fawcett, F.S., Smith, W.C., and Coffman, D.D., J. Am. Chem. Soc., 1960, vol. 82, p. 539.
Markovsky, L. and Pashinnik, V., Reviews on Heteroatom Chemistry, Oae, S., Ohno, A., and Furukawa, N., Eds., Tokyo: MYU, 1989, vol. 2, p. 112.
Szabó, D., Kuti, M., Kapovits, I., Rábai, J., Kucsman, Á., Argay, G., Czugler, M., Kálmán, A., and Párkányi, L., J. Mol. Struct., 1997, vol. 415, p. 1.
Szabó, D., Kapovits, I., Kucsman, Á., Huszthy, P., Argay, G., Czugler, M., Fülöp, V., Kálmán, A., Koritsánsky, T., and Párkányi, L., J. Mol. Struct., 1993, vol. 300, p. 23.
Adzima, L.J., Chiang, C.C., Paul, I.C., and Martin, J.C., J. Am. Chem. Soc., 1978, vol. 100, p. 953.
Adam, T., Ruff, F., Kapovits, I., Szabo, D., and Kucsman, A., J. Chem. Soc., Perkin Trans. 2, 1998, p. 1269.
Moskalik, M.Yu., Astakhova, V.V., and Shainyan, B.A., Russ. J. Org. Chem., 2013, vol. 49, p. 761.
Roesky, H.W. and Schönfelder, L., Chem. Ber., 1982, vol. 115, p. 1460.
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, Revision A.01, Wallingford CT: Gaussian, 2009.
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Original Russian Text © B.A. Shainyan, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 4, pp. 491–494.
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Shainyan, B.A. Stability of S,S-diamino-λ4-sulfanes. Russ J Org Chem 51, 472–475 (2015). https://doi.org/10.1134/S1070428015040028
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DOI: https://doi.org/10.1134/S1070428015040028