Facile Preparation of 1,2-Diols from Chalcones: An NMR Spectroscopy and X-Ray Crystallography StudyReportar como inadecuado




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Structures of 2-naphthalen-2-ylmethyl-2,3-dihydro-1H-indene-1,2-diol C20H18O2, compound 1 and 1-3,4-dimethoxyphenyl-3-methoxy-3-4-nitrophenylpropane-1,2-diol chloroform C18H21NO7·CHCl3 compound 2 were established by spectral and X-ray diffraction studies. Compound 1 crystallizes in the orthorhombic space group P212121 with unit cell parameters a = 5.2177 6, b = 13.903 2, c = 21.121 2 A, Z = 4. Compound 2 crystallizes in the triclinic space group P-1 with unit cell parameters a = 9.238 1, b = 9.879 1, c = 12.636 1 A, α = 102.004 1, β = 92.356 1, γ = 90.779 1o, Z = 2. These two new molecules arise from a facile preparation of 1,2-diols from chalcones and have been fully characterized. Based on the crystallographic information obtained for compound 1, the relative configuration for the chiral centers is 1S and 2S. In structure 1, both hydroxyl groups adopt an anti-conformation with a torsion angle O1-C1-C2-O2 value of 93.1 2o in molecule 2, both hydroxyl groups adopt a trans-conformation with a torsion angle O1-C1-C2-O2 value of -171.0 2。. In both structures, the molecules in the crystal are linked by intermolecular hydrogen bonds O-H···O and C-H···O interactions and adjacent molecules are interconnected by intermolecular weak C-H···π and C-H···Cl interactions which give additional support to molecular packing stability.

KEYWORDS

C20H18O2, C18H21NO7·CHCl3 Diols, Chal-cones

Cite this paper

Obregón-Mendoza, M. , Estévez-Carmona, M. , Escobedo-Martínez, C. , Soriano-García, M. and Enríquez, R. 2015 Facile Preparation of 1,2-Diols from Chalcones: An NMR Spectroscopy and X-Ray Crystallography Study. International Journal of Organic Chemistry, 5, 137-146. doi: 10.4236-ijoc.2015.53015.





Autor: Marco A. Obregón-Mendoza1, María Miriam Estévez-Carmona1, Carolina Escobedo-Martínez2, Manuel Soriano-García1*, Raúl G. Enr

Fuente: http://www.scirp.org/



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