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Hydrogen bonding network in a chiral alcohol: (1R,2S,5R)-(−)-menthol. Conformational preference studied by IR–Raman–VCD spectroscopies and quantum chemical calculations

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Abstract

A study of the molecular structure of (1R,2S,5R)-(−)-menthol and the hydrogen bond networks formed by this species in solution is carried out. Molecular structures of monomers and H-bonded dimers and trimers of the title compound are optimized using quantum chemical calculations in the isolated molecule approach. In addition, IR, Raman and VCD techniques are used to study CCl4 solutions and thin films of the target compound. Their corresponding vibrational spectra are then analysed, both theoretically (HF and DFT) and experimentally, to characterize the different monomers (rotamers) and H-bonded oligomer species in menthol solutions as a function of the concentration.

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Acknowledgments

This work was supported by the Junta de Andalucía (project P08-FQM-04096). The authors thank the University of Jaén for continuing financial support and its CICT for instrumental facilities. Juan Ramón Avilés Moreno expresses thanks to the Junta de Andalucía for a Post-Doc grant. We are grateful to a native English Speaker (Jean Louise Sanders) for reviewing the grammar. The authors are also grateful to D. Francisco Hermoso Torres for his help in the laboratory.

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Authors and Affiliations

  1. Grupo de Química Física Teórica y Experimental, Departamento de Química Física y Analítica, Facultad de Ciencias Experimentales, Universidad de Jaén, Edificio B3., Campus Las Lagunillas, 23071, Jaén, Spain

    Juan Ramón Avilés Moreno, Francisco Partal Ureña & Juan Jesús López González

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  1. Juan Ramón Avilés Moreno
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  2. Francisco Partal Ureña
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  3. Juan Jesús López González
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Correspondence to Juan Ramón Avilés Moreno.

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Avilés Moreno, J.R., Partal Ureña, F. & López González, J.J. Hydrogen bonding network in a chiral alcohol: (1R,2S,5R)-(−)-menthol. Conformational preference studied by IR–Raman–VCD spectroscopies and quantum chemical calculations. Struct Chem 24, 671–680 (2013). https://doi.org/10.1007/s11224-012-0118-8

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  • DOI: https://doi.org/10.1007/s11224-012-0118-8

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