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

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 determine...

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Bibliographic Details
Published inCentral European journal of chemistry Vol. 7; no. 1; pp. 14 - 19
Main Authors Todorov, Petar T., Petrova, Rosica N., Naydenova, Emilia D., Shivachev, Boris L.
Format Journal Article
LanguageEnglish
Published Heidelberg SP Versita 01.03.2009
Versita
De Gruyter
Subjects
Biochemistry
Biological and Medical Physics
Biophysics
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Crystal structure
DFT calculations
Geochemistry
Hydrogen bonds
Research Article
Spirohydantoins
Hydrogen bonds
Spirohydantoins
DFT calculations
Crystal structure
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Summary: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.
ISSN:1895-1066
2391-5420
1644-3624
2391-5420
DOI:10.2478/s11532-008-0087-3