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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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1865-7117
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Volume 73, Issue 5

Issues

Triclinic conformational polymorph of N,N,N′,N′-tetrakis(2-cyanoethyl)-1,2-ethylenediamine (TCED)

Bartłomiej Bereska
  • Institute of Heavy Organic Synthesis “Blachownia”, Speciality Chemicals Department, 47-225 Kędzierzyn-Koźle, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Krystyna Czaja / Błażej Dziuk / Bartosz Zarychta / Krzysztof Ejsmont / Jolanta Iłowska
  • Institute of Heavy Organic Synthesis “Blachownia”, Speciality Chemicals Department, 47-225 Kędzierzyn-Koźle, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Michał Szmatoła
  • Institute of Heavy Organic Synthesis “Blachownia”, Speciality Chemicals Department, 47-225 Kędzierzyn-Koźle, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Agnieszka Bereska
  • Institute of Heavy Organic Synthesis “Blachownia”, Speciality Chemicals Department, 47-225 Kędzierzyn-Koźle, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2018-04-13 | DOI: https://doi.org/10.1515/znb-2018-0015

Abstract

The crystal and molecular structures of two polymorphs of N,N,N′,N′-tetrakis(2-cyanoethyl)-1,2-ethylenediamine have been characterized by X-ray diffraction along with density functional theory (DFT) studies. The molecules differ from each other by conformation. N,N,N′,N′-tetrakis(2-cyanoethyl)-1,2-ethylenediamine has been synthesized by cyanoethylation of ethylenediamine. Cyanoethylation of vicinal diamines is important for the synthesis of hyperbranched polymeric materials applied as catalysts, surfactants and encapsulating agents in drug delivery systems. The molecular geometry of N,N,N′,N′-tetracyanoethyl-1,2-ethylenediamine is similar to that of homologous compounds. DFT calculations were performed to analyze the differences in the molecular geometry of the studied compounds in a crystalline state and for an isolated molecule.

Keywords: catalysis; conformation; crystal structure; X-ray structure determination

References

  • [1]

    E. Buhleier, W. Wehner, F. Vögtle, Synthesis 1978, 9, 155.Google Scholar

  • [2]

    H. B. Mekelburger, W. Jaworek, F. Vögtle, Angew. Chem., Int. Ed. Engl. 1992, 31, 1571.CrossrefGoogle Scholar

  • [3]

    D. A. Tomalia, Aldrichim. Acta 1993, 26, 91.Google Scholar

  • [4]

    H. A. Bruson, Organic Reactions, Vol. 5, John Wiley and Sons, New York, 1949, pp. 79−135.Google Scholar

  • [5]

    J. Nowicki, B. Bereska, E. Dziwiński, M. Organek, J. Iłowska, A. Bereska, Ind. Eng. Chem. Res. 2016, 55, 1827.CrossrefGoogle Scholar

  • [6]

    J. Gao, X.-Y. Xu, T.-T. Xu, J. Ni, Q.-L Liu, J. Struct. Chem. 2006, 47, 383.CrossrefGoogle Scholar

  • [7]

    F. H. Allen, Acta Crystallogr. 2002, B58, 380.Google Scholar

  • [8]

    CrysAlis CCD and CrysAlis Red, Oxford Diffraction Ltd., Abingdon, Oxford (UK) 2008.Google Scholar

  • [9]

    G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112.Google Scholar

  • [10]

    G. M. Sheldrick, Acta Crystallogr. 2015, C71, 3.Google Scholar

  • [11]

    A. D. Becke, Phys. Rev. A. 1988, 38, 3098.CrossrefGoogle Scholar

  • [12]

    A. D. Becke, J. Chem. Phys. 1993, 98, 5648.CrossrefGoogle Scholar

  • [13]

    C. Lee, W. Yang, R. G. Parr, Phys. Rev. B. 1988, 37, 785.CrossrefGoogle Scholar

  • [14]

    M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, 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, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Gaussian, Inc., Wallingford, CT (USA) 2009.Google Scholar

  • [15]

    B. Bereska, K. Czaja, J. Nowicki, J. Iłowska, A. Bereska, M. Muszyńki, M. Szmatoła, R. Grabowski, Chem. Select 2017, 2, 10020.Google Scholar

About the article

Received: 2018-01-16

Accepted: 2018-03-25

Published Online: 2018-04-13

Published in Print: 2018-05-24


Citation Information: Zeitschrift für Naturforschung B, Volume 73, Issue 5, Pages 305–309, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0015.

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