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Synthesis and structural study of ethylmethylsilanediol by quantum chemical calculations and IR and Raman spectroscopies

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Abstract

The intrinsic instability of small alkylsilanediols and their propensity toward self-condensation have been the main determiners of the scarce number of experimental works dealing with their synthesis and vibrational characterization. This is the case of the title compound, ethylmethylsilanediol (EMSD), which preparation and purification is, to the best of our knowledge, firstly reported in the present work. Hence, we also report the first records of the IR and Raman spectra of the molecule that have been thoroughly analyzed and completely assigned with the support of DFT calculations. Further, as a previous step of the vibrational assignment, we accomplished a thorough conformational analysis that allowed indentifying five conformations that represent minima on the potential energy surface (PES) of the molecule, depending on the different arrangement that both, the alkyl side chain and the –OH groups, can adopt. Finally, natural bond orbital (NBO) calculations were implemented to justify the stability order and the calculated geometries for the set of conformers in terms of the stabilization derived from the anomeric effect.

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Acknowledgments

The authors thank Andalussian government for funding (FQM173, FQM182) and the CICT facilities of the University of Jaén. P.G.R.O. thanks Spanish Ministerio de Educación for a Ph.D studentship (AP2009-3949) supporting this work.

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Authors and Affiliations

  1. Physical and Analytical Chemistry Department, University of Jaén, Campus Las Lagunillas, 23071, Jaén, Spain

    M. P. G. Rodríguez Ortega, M. Montejo, F. Márquez & J. J. López González

  2. Inorganic and Organic Chemistry Department, University of Jaen, Campus Las Lagunillas, 23071, Jaen, Spain

    A. Marchal Ingraín

Authors
  1. M. P. G. Rodríguez Ortega
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  2. M. Montejo
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  3. A. Marchal Ingraín
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  4. F. Márquez
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  5. J. J. López González
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Correspondence to J. J. López González.

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Rodríguez Ortega, M.P.G., Montejo, M., Marchal Ingraín, A. et al. Synthesis and structural study of ethylmethylsilanediol by quantum chemical calculations and IR and Raman spectroscopies. J Sol-Gel Sci Technol 61, 258–267 (2012). https://doi.org/10.1007/s10971-011-2622-5

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  • DOI: https://doi.org/10.1007/s10971-011-2622-5

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