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An XRD Study of Molecular and Crystalline Structures of (Z)-3-(Benzoxazol-2-Ylthio)-3-Phenyl-2-Propenonitrile and an 1H NMR Study of Its E/Z Isomerization in Solutions

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Abstract

According to X-ray diffraction data, crystalline 3-(benzoxazol-2-ylthio)-3-phenyl-2-propenonitrile is a substantially nonplanar Z-isomer. The resulting single crystal has layered structure as a result of π–π stacking. 1H NMR data testify small amounts of E-isomer in the samples dissolved in chloroform.

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References

  1. G. Evindar and R. A. Batey. J. Org. Chem., 2006, 71, 1802.

    Article  CAS  PubMed  Google Scholar 

  2. S. Ramineni, R. K. Kannasani, and V. V. S. Peruri. Green Chem. Lett. Rev., 2014, 7,85.

    Article  CAS  Google Scholar 

  3. M. O. Chaney, P. V. Demarco, N. D. Jones, and J. L. Occolowitz. J. Am. Chem. Soc., 1974, 96, 1932.

    Article  CAS  PubMed  Google Scholar 

  4. S. P. B. Ovenden, J. L. Nielson, C. H. Liptrot, R. H. Willis, D. M. Tapiolas, A. D. Wright, and C. A. Motti. J. Nat. Prod., 2011, 74,65.

    Article  CAS  PubMed  Google Scholar 

  5. T. Kusumi, T. Ooi, M. R. Walchli, and H. Kakisawa. J. Am. Chem. Soc., 1988, 110, 2954.

    Article  CAS  Google Scholar 

  6. J. Boyer, E. Arnoult, M. Médebielle, J. Guillemont, J. Unge, and D. Jochmans. J. Med. Chem., 2011, 54, 7974.

    Article  CAS  PubMed  Google Scholar 

  7. G. Singh, M. Kaur, C. Mohan, and S. Prashar. Indo Am. J. Pharm. Res., 2013, 3, 6113.

    Google Scholar 

  8. S. Sato, T. Kajiura, M. Noguchi, K. Takehana, T. Kobayasho, and T. Tsuji. Antibiot., 2001, 54,102.

    Article  CAS  Google Scholar 

  9. R. M. Samia, A. A. Fawzia, E.-H. A. M. Soad, E. S. M. Mona, B. H. Mona, and S. A. Manal. Eur. J. Med. Chem., 2005, 40,949.

    Article  CAS  Google Scholar 

  10. K. Seth, S. K. Garg, R. Kumar, P. Purohit, V. S. Meena, R. Goyal, U. C. Banerjee, and A. K. Chakraborti. ACS Med. Chem. Lett., 2014, 5,512.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. L. V. Andriyankova, N. D. Abramova, and E. I. Kositsyna. Bull. Acad. Sci. USSR. Div. Chem. Sci., 1990, 1390.

    Google Scholar 

  12. V. V. Nosyreva, L. V. Andriyankova, A. G. Mal'kina, A. V. Afonin, and B. A. Trofimov. Russ. J. Org. Chem., 2001, 37,906.

    Article  Google Scholar 

  13. L. V. Andriyankova, S. A. Zhivet'ev, A. G. Mal'kina, P. N. Kudryakova, E. I. Kositsyna, L. N. Il'icheva, I. A. Ushakov, A. V. Afonin, and B. A. Trofimov. Russ. J. Org. Chem., 2002, 38, 1738.

    Article  Google Scholar 

  14. L. V. Andriyankova, S. A. Zhivet'ev, A. G. Mal'kina, M. A. Andriyankov, A. V. Afonin, and B. A. Trofimov. Chem. Heterocycl. Compd., 2002, 1115.

    Google Scholar 

  15. G. M. Sheldrick. Acta Crystallogr., 2008, D64,112.

    Article  CAS  Google Scholar 

  16. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Cliford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. M. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople. Gaussian 09, Revision E.01, Gaussian Inc., Wallingford CT, 2009.

    Google Scholar 

  17. A. D. Becke. J. Chem. Phys., 1993, 98, 5648.

    Article  CAS  Google Scholar 

  18. C. T. Lee, W. T. Yang, and R. G. Parr. Phys. Rev. B, 1988, 37,785.

    Article  CAS  Google Scholar 

  19. R. Krishnan, J. S. Binkley, R. Seeger, and J. A. Pople. J. Chem. Phys., 1980, 72,650.

    Article  CAS  Google Scholar 

  20. J. Tomasi, B. Mennucci, and R. Cammi. Chem. Rev., 2005, 105, 2999.

    Article  CAS  PubMed  Google Scholar 

  21. G. Scalmani and M. J. Frisch. J. Chem. Phys., 2010, 132,15.

    Article  CAS  Google Scholar 

  22. R. Ditchfield. Mol. Phys., 1974, 27,789.

    Article  CAS  Google Scholar 

  23. K. Wolinski, J. F. Hilton, and P. Pulay. J. Am. Chem. Soc., 1990, 112, 8251.

    Article  CAS  Google Scholar 

  24. A. M. Sarotti and S. C. Pellegrinet. J. Org. Chem., 2009, 74, 7254.

    Article  CAS  PubMed  Google Scholar 

  25. A. V. Afonin, D. V. Pavlov, I. A. Ushakov, E. Yu. Schmidt, and A. I. Mikhaleva. Magn. Reson. Chem., 2009, 47,879.

    Article  CAS  PubMed  Google Scholar 

  26. A. V. Afonin, D. V. Pavlov, A. I. Albanov, E. P. Levanova, and G. G. Levkovskaya. Magn. Reson. Chem., 2011, 49,740.

    Article  CAS  PubMed  Google Scholar 

  27. C. Janiak. J. Chem. Soc., Dalton Trans., 2000, 3885.

    Google Scholar 

  28. L. V. Andriyankova, L. P. Nikitina, K. V. Belyaeva, A. G. Mal'kina, A. V. Afonin, A. V. Vashchenko, V. I. Smirnov, and B. A. Trofimov. Chem. Heterocycl. Compd., 2014,876.

    Google Scholar 

  29. K. V. Belyaeva, L. V. Andriyankova, L. P. Nikitina, A. V. Afonin, I. A. Ushakov, I. Yu. Bagryanskaya, and B. A. Trofimov. Tetrahedron, 2014, 70, 1091.

    Article  CAS  Google Scholar 

  30. K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, A. V. Vashchenko, and B. A. Trofimov. Russ. Chem. Bull., 2017, 2258.

    Google Scholar 

  31. A. V. Afonin, A. V. Vashchenko, A. I. Albanov, V. I. Nosyreva, A. G. Mal'kina, and B. A. Trofimov. Magn. Reson. Chem., 2017, 55,563.

    Article  CAS  PubMed  Google Scholar 

  32. B. A. Trofimov, L. V. Andriyankova, S. I. Shaikhudinova, T. I. Kazantseva, A. G. Mal'kina, and A. V. Afonin. Synthesis, 2002,853.

    Google Scholar 

  33. L. V. Andriyankova, A. G. Mal'kina, A. V. Afonin, and B. A. Trofimov. Mendeleev Commun., 2003,186.

    Google Scholar 

  34. L. V. Andriyankova, A. G. Mal'kina, L. P. Nikitina, K. V. Belyaeva, I. A. Ushakov, A. V. Afonin, M.V. Nikitin, and B. A. Trofimov. Tetrahedron., 2005, 61, 8031.

    Article  CAS  Google Scholar 

  35. B. A. Trofimov, L. V. Andriyankova, R. T. Tlegenov, A. G. Mal'kina, A. V. Afonin, L. N. Il'icheva, and L. P. Nikitina. Mendeleev Commun., 2005, 33.

    Google Scholar 

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia

    A. V. Afonin, A. V. Vashchenko, L. P. Nikitina & A. G. Mal’kina

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  1. A. V. Afonin
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  2. A. V. Vashchenko
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  3. L. P. Nikitina
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  4. A. G. Mal’kina
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Correspondence to A. V. Afonin.

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Original Russian Text © 2018 A. V. Afonin, A. V. Vashchenko, L. P. Nikitina, A. G. Mal′kina.

Translated from Zhurnal Strukturnoi Khimii, Vol. 59, No. 7, pp. 1640–1647, September-October, 2018.

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Afonin, A.V., Vashchenko, A.V., Nikitina, L.P. et al. An XRD Study of Molecular and Crystalline Structures of (Z)-3-(Benzoxazol-2-Ylthio)-3-Phenyl-2-Propenonitrile and an 1H NMR Study of Its E/Z Isomerization in Solutions. J Struct Chem 59, 1580–1587 (2018). https://doi.org/10.1134/S0022476618070090

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  • DOI: https://doi.org/10.1134/S0022476618070090

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