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Inversion of configuration in the aminolysis of N-benzenesulfonylbenzimidoyl chloride. Crystal and molecular structure of N2-benzenesulfonyl-N1-(3-nitrophenyl)benzamide

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

The E-molecular configuration of N2-benzenesulfonyl-N1-(3-nitrophenyl)benzamidine has been verified by x-ray structural investigation, which also made it possible to confirm the addition-elimination mechanism which had been proposed earlier for the reactions of N-aryl-sulfonylbenzimidoyl chlorides with aromatic amines in aprotic reaction media. Molecules of (II) are associated with one another in the crystal structure via H-bonds in a chain, while neighboring chains are associated with one another by means of the so-called “stacking” interactions.

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Literature cited

  1. L. M. Litvinenko, V. A. Mikhailov, L. P. Drizhd, and V. A. Savelova, Zh. Org. Khim.,21, 181 (1985).

    Google Scholar 

  2. R. G. Gerr, A. I. Yanovskii, and Yu. T. Struchkov, Kristallografiya,28, 1029 (1983).

    Google Scholar 

  3. D. S. Yufit, Yu. T. Struchkov, V. A. Savelova, et al., Zh. Strukt. Khim.,27, 182 (1986).

    Google Scholar 

  4. J. E. Johnson, E. A. Nalley, Ch. Weidig, and M. Arfan, J. Org. Chem.,46, 3623 (1981).

    Google Scholar 

  5. A. F. Hegarty and A. Chandler, J. Chem. Soc., Chem. Commun., 130 (1980).

  6. A. F. Hegarty, M. T. McCormack, B. J. Hathaway, and L. Hullet, J. Chem. Soc., Perkin Trans., 2, 1136 (1977).

    Google Scholar 

  7. P. Deslongshamps, Tetrahedron,31, 2463 (1975).

    Google Scholar 

  8. Z. Rappoport, Acc. Chem. Res.,14, 7 (1981).

    Google Scholar 

  9. M. Alleaume, A. Gulko, F. H. Herbstein, et al., Acta Crystallogr.,B32, 669 (1976).

    Google Scholar 

  10. H. P. Koch and W. E. Moffitt, J. Chem. Soc., Faraday Trans.,41, 7 (1951).

    Google Scholar 

  11. V. V. Pirozhenko, A. N. Chernega, I. E. Boldeskul, Zh. Obshch. Khim.,53, 373 (1983).

    Google Scholar 

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 783–787, April, 1988.

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Yufit, D.S., Struchkov, Y.T., Mikhailov, V.A. et al. Inversion of configuration in the aminolysis of N-benzenesulfonylbenzimidoyl chloride. Crystal and molecular structure of N2-benzenesulfonyl-N1-(3-nitrophenyl)benzamide. Russ Chem Bull 37, 667–670 (1988). https://doi.org/10.1007/BF01455473

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  • DOI: https://doi.org/10.1007/BF01455473

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