Marco A. Obregón-Mendoza¹, María Miriam Estévez-Carmona¹, Carolina Escobedo-Martínez², Manuel Soriano-García^1*, Raúl G. Enríquez^1*

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¹ Instituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, México City, México.
² Departamento de Farmacia, División de Ciencias Naturales y Exactas del Campus Guanajuato, Universidad de Guanajuato, México.
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Abstract: 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-nitrophenyl)propane-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 (1)^o, 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 (2)^o [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.

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