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Central European Journal of Chemistry

, Volume 7, Issue 1, pp 14–19 | Cite as

Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins

  • Petar T. Todorov
  • Rosica N. Petrova
  • Emilia D. Naydenova
  • Boris L. ShivachevEmail author
Research Article

Abstract

The crystal structures of 3-amino-cycloheptanespiro-4′-imidazolidine-2′,5′-dione (I) {systematic name: 3-amino-1,3-diazaspiro[4.6] undecane-2,4-dione} and 3-amino-cyclooctanespiro-4′-imidazolidine-2′,5′-dione (II) {systematic name: 3-amino-1,3-diazaspiro[4.7] dodecane-2,4-dione}, have been determined. In both compounds the polar hydantoin groups cause molecules to aggregate via N-H...O and N-H...N interactions, forming a layer structure, in which the cycloalkane rings project outwards from the central, more polar, region. The observed molecular structure is compared with that calculated by density functional theory methods.

Keywords

Spirohydantoins Crystal structure Hydrogen bonds DFT calculations 

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Copyright information

© © Versita Warsaw and Springer-Verlag Berlin Heidelberg 2009

Authors and Affiliations

  • Petar T. Todorov
    • 1
  • Rosica N. Petrova
    • 2
    • 3
  • Emilia D. Naydenova
    • 1
  • Boris L. Shivachev
    • 3
    • 4
    Email author
  1. 1.Department of Organic ChemistryUniversity of Chemical Technology and MetallurgySofiaBulgaria
  2. 2.Department of Advanced Materials Science and Engineering, Faculty of EngineeringYamaguchi UniversityUbeJapan
  3. 3.Central Laboratory of Mineralogy and CrystallographyBulgarian Academy of SciencesSofiaBulgaria
  4. 4.Department of Structural BiologyUniversity of Pittsburgh School of MedicinePittsburghUSA

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