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Crystal and molecular structure of the “asymmetric” ethylenediamine-N,N-di-3-propionic acid monohydrate

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Abstract

A new complexing agent the “asymmetric” ethylenediamine-N,N-di-3-propionic acid (as.EDDP) is obtained. The crystal structure of the new compound is determined by single-crystal X-ray diffraction. C8H16N2O4·H2O crystals are monoclinic; space group P21/c, a = 12.7416(4) Å, b = 6.5470(2) Å, c = 12.1908(4) Å, β = 93.100(1)°, Z = 4, ρ x = 1.454 mg/m3, and R 1 (I > 2.0σ(I)) = 0.0326. In the solid form, the as.EDDP molecule has a double betaine structure:

The intramolecular hydrogen bonds with the betaine proton of the tertiary nitrogen atom are formed with the participation of one oxygen atom of the carboxyl group of each 3-propionic fragment, which forms two N(1)-H(1N)-bonded six-membered H-cycles. The intermolecular hydrogen bonds are formed between the three hydrogen atoms of the protonated primary nitrogen atom and the oxygen atoms of the 3-propionic fragments of three other as.EDDP molecules. The water molecule participates in the formation of intermolecular hydrogen bonds with the oxygen atom of one carboxyl group of the molecule.

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References

  1. R. C. Courtney, S. Chaberek Jr., and A. E. Martell, J. Am. Chem. Soc., 75, 4814 (1953).

    Article  CAS  Google Scholar 

  2. N. M. Dyatlova, V. Ya. Temkina, and I. D. Kolpakova, Complexing Agents [in Russian], Khimiya, Moscow (1970).

    Google Scholar 

  3. L. K. Neudachina, Y. G. Yatluk, and N. V. Baranova, Russ. Chem. Bull., 55, No. 5, 828 (2006).

    Article  CAS  Google Scholar 

  4. H. Kodama and C. Fujisawa, Curr. Drug Metab., 13, No. 3, 237 (2012).

    Article  CAS  Google Scholar 

  5. H. Itabashi, Y. Shigeta, H. Kawamoto, and H. Akaiwa, Anal. Sci., 16, No. 11, 1179 (2000).

    Article  CAS  Google Scholar 

  6. L. M. Shkol’nikova, K. D. Suyarov, A. V. Gasparyan, et al., J. Struct. Chem., 30, No. 6, 944–956 (1989).

    Article  Google Scholar 

  7. V. V. Glodjovic, G. P. Radic, S. M. Stanic, et al., J. Serb. Chem. Soc., 76, No. 7, 995 (2011).

    Article  CAS  Google Scholar 

  8. M. Mori, B. H. Gahwiler, and U. Gerber,, J. Physiology, 539, No. 1, 191 (2002).

    Article  CAS  Google Scholar 

  9. Bruker, Programs APEX II, Version 2.0-1; SAINT, Version 7.23A; SADABS, Version 2004/1; XPREP, Version 2005/2; SHELXTL, Version 6.1, Bruker AXS Inc., Madison, WI, USA (2005).

  10. G. M. Sheldrick, Acta Crystallogr., A64, 112 (2008).

    Article  Google Scholar 

  11. A. V. Gasparyan, L. M. Shkol’nikova, N. V. Tsirul’nikova, et al., J. Struct. Chem., 26, No. 3, 447–451 (1985).

    Article  Google Scholar 

  12. F. J. Strieter, D. H. Templeton, R. F. Scheuerman, and R. L. Sass, Acta Crystallogr., 15, 1233–1239 (1962).

    Article  Google Scholar 

Download references

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Authors and Affiliations

  1. Institute of Chemical Reagents and High-Purity Chemical Substances, Moscow, Russia

    O. N. Podmareva & N. V. Tsirul’nikova

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

    Z. A. Starikova

Authors
  1. O. N. Podmareva
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  2. Z. A. Starikova
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  3. N. V. Tsirul’nikova
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Correspondence to O. N. Podmareva.

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Original Russian Text © 2013 O. N. Podmareva, Z. A. Starikova, N. V. Tsirul’nikova

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Translated from Zhurnal Strukturnoi Khimii, Vol. 54, No. 6, pp. 1071–1076, November–December, 2013.

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Podmareva, O.N., Starikova, Z.A. & Tsirul’nikova, N.V. Crystal and molecular structure of the “asymmetric” ethylenediamine-N,N-di-3-propionic acid monohydrate. J Struct Chem 54, 1101–1106 (2013). https://doi.org/10.1134/S0022476613060140

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  • DOI: https://doi.org/10.1134/S0022476613060140

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