Structural effects and hydrogen bonds on N

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• 作者：Sonia Torrico Vallejos ; Mauricio F. Erben ; Rol ; Boese ; Oscar E. Piro ; Eduardo E. Castellano ; Carlos O. Della Vé ; dova
• 关键词：Hydrogen bonding ; X-ray structure ; Urea ; Conformational study
• 刊名：Journal of Molecular Structure
• 出版年：2009
• 出版时间：29 January 2009
• 年：2009
• 卷：918
• 期：1-3
• 页码：146-153
• 全文大小：413 K

文摘

Pure N,N′-di(methoxycarbonylsulfenyl)urea, [CH₃OC(O)SNH]₂CO, is quantitatively prepared by the hydrolysis reaction of CH₃OC(O)SNCO and characterized by ¹H NMR, GC–MS and FTIR spectroscopy techniques. Structural and conformational properties are analyzed using a combined approach with data obtained from X-ray diffraction, vibrational spectra and theoretical calculation methods. The IR and Raman spectra for normal and deuterated species are reported. The crystal structure of [CH₃OC(O)SNH]₂CO was determined by X-ray diffraction methods. The substance crystallizes in the orthorhombic P2₁2₁2 space group with a = 9.524(2), b = 12.003(1), c = 4.481(1) Å, and Z = 2 moieties in the unit cell. The molecule is sited on a twofold crystallographic axis (C₂) parallel to c and shows the anti–anti conformation (S–N single bonds antiperiplanar with respect to the opposite C–N single bonds in sulfenyl-ureasic group). Neighboring molecules are arranged in a chain motif that extends along the C₂-axis and is held by bifurcated NHOHN intermolecular bonds. A local planar symmetry is observed in the crystal for the central –SN(H)C(O)N(H)S– skeleton. Experimental and calculated data allow to trace this structural feature to the occurrence of N–HOC hydrogen bonding interactions. Calculated vibrational and structural properties are in good agreement with the experimentally determined features.