Back
 IJOC  Vol.5 No.3 , September 2015
Facile Preparation of 1,2-Diols from Chalcones: An NMR Spectroscopy and X-Ray Crystallography Study
Marco A. Obregón-Mendoza1, María Miriam Estévez-Carmona1, Carolina Escobedo-Martínez2, Manuel Soriano-García1*, Raúl G. Enríquez1*
Show more
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.
References

[1]   Corey, E.J. and Winter, R.A.E. (1963) A New, Stereospecific Olefin Synthesis from 1,2-Diols. Journal of the American Chemical Society, 85, 2677-2678.
http://dx.doi.org/10.1021/ja00900a043

[2]   Notz, W. and List, B. (2000) Catalytic Asymmetric Synthesis of Anti-1,2-diols. Journal of the American Chemical Society, 122, 7386-7387.
http://dx.doi.org/10.1021/ja001460v

[3]   Periasamy, M. and Thirumalaikumar, M. (2000) Methods of Enhancement of Reactivity and Selectivity of Sodium Borohydride for Applications in Organic Synthesis. Journal of Organometallic Chemistry, 609, 137-151.
http://dx.doi.org/10.1016/S0022-328X(00)00210-2

[4]   Fuji, H., Ohima, K. and Utimoto, K. (1991) A Facile and Selective 1,2-Reduction of Conjugated Ketones with NaBH4 in the Presence of CaCl2. Chemistry Letters, 20, 1847-1848.
http://dx.doi.org/10.1246/cl.1991.1847

[5]   Baluja, M.G., Municio, A.M. and Vega, S. (1964) Reactivity of lO,p-Unsaturated Ketones toward Sulfhydryl Compounds and Their Antifungal Activity. Chemistry and Industry (London), 50, 2053.

[6]   Dimmock, J.R., Raghavan, S.K., Logan, B.M. and Bigam, G.E. (1983) Antileukemic Evaluation of Some Mannich Bases Derived from 2-Arylidene-1,3-diketones. European Journal of Medicinal Chemistry, 18, 248-254.

[7]   Armarego, W.L.F. and Perrin, D.D. (1997) Purification of Laboratory Chemicals. 4th Edition, Butterworth-Heinemann, Oxford.

[8]   Bruker (2009) APEX2, SAINT and SADABS. Bruker AXS Inc., Madison.

[9]   Sheldrick, G.M. (2007) A Short History of SHELX. Acta Crystallographica, A64, 112-122.
http://dx.doi.org/10.1107/S0108767307043930

[10]   Flack, H.D. (1983) Onenantiomorph-Polarity Estimation. Acta Crystallographica, A39, 876-881.
http://dx.doi.org/10.1107/S0108767383001762

[11]   Brandenburg, K. (2006) DIAMOND. Version 3.1c. Crystal Impact GbR, Bonn.

[12]   Farrugia, L.J. (2012) WinGX and ORTEP for Windows: An Update. Journal of Applied Crystallography, 45, 849-854.
http://dx.doi.org/10.1107/S0021889812029111

[13]   Nardelli, M. (1983) PARST: A System of Fortran Routines for Calculating Molecular Structure Parameters from Results of Crystal Structure Analyses. Computers & Chemistry, 7, 95-98.
http://dx.doi.org/10.1016/0097-8485(83)85001-3

[14]   Nardelli, M. (1995) PARST95—An Update to PARST: A System of Fortran Routines for Calculating Molecular Structure Parameters from the Results of Crystal Structure Analyses. Journal of Applied Crystallography, 28, 659.
http://dx.doi.org/10.1107/S0021889895007138

[15]   Bernstein, J., Davis, R.E., Shimoni, L. and Chamg, N.-L. (1995) Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals. Angewandte Chemie International Edition (English), 34, 1555-1573.
http://dx.doi.org/10.1002/anie.199515551

 
 
Top