Carbamoylated oximes 1 form 1:1 molecular complexes 4 with N,N-dialkyl-N′-phenylurea when stirred in THF or ether at room temperature for short time in good yields. The molecular complexes 4a–e were isolated and characterized by analytical and spectral means. X-ray crystallographic analysis for complex 4a was performed. In this paper, we report the use of complex 4a and its moieties as building blocks to form non-interacting polymeric zigzag chains by inter- and intramolecular hydrogen bonds along b-axis, and details of supramolecular architecture of 4a. There is a intramolecular H–H interaction between hydrogen of urea NH and neighboring hydrogen of diisopropyl's CH linked to the other urea nitrogen. In addition, to obtain the most favorable orientation of the moieties of the title complex, PM3 semi-empirical quantum mechanical calculations were performed and then results from X-ray crystallography and computational modeling were compared.
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N,N-Diethyl-N′-phenylurea and acetophenone oxime were refluxed in THF for 24 h and no trace of 1 was obtained however when the reaction was performed in the presence of equimolar amount of DMAD the reaction proceeds for short time and the products were dimethyl N,N-dialkylaminomaleate and corresponding phenylcarbamoylated acetophenone oxime (for more information see: Coşkun, N.; Arıkan, N. Turk. J. Chem., 2003, 27, 15).
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We are grateful to Uludağ and Dokuz Eylül Universities's Research Funds for their financial supports (respective project numbers: 2001-2 and 04.KB.FEN.100). In addition, Hasan Karabıyık would like to thank TÜBİTAK (The Scientific and Technical Research Council of Turkey) for partial financial support.
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Coşkun, N., Parlar, A., Karabıyık, H. et al. Supramolecular architecture of phenylcarbamoylated acetone oxime 1,1-diisopropyl-3-phenylurea] complex. Struct Chem 17, 431–438 (2006). https://doi.org/10.1007/s11224-006-9063-8
- Molecular complex
- Hydrogen bonding
- H–H interaction
- Carbamoylated oxime