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Stereochemistry and spectroscopic analysis of bis-Betti base derivatives of 2,3-dihydroxynaphthalene

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Abstract

Density functional theory (DFT) was used to study the stereochemistry, thermodynamic stability, and spectra of recently synthesized bis-Betti base derivatives of 2,3-dihydroxynaphthalene obtained through multicomponent reactions of 2,3-dihydroxynaphthalene with aminoisoxazole and benzaldehyde derivatives. The stereochemistry of the products was investigated by theoretically calculating the infrared (IR) and proton nuclear magnetic resonance (1H NMR) spectra of the diastereomers and comparing them to the corresponding experimental data. The thermochemical properties of the reactions, including the enthalpy, internal energy, entropy, and Gibbs free energy, were also calculated. The diastereoselectivity of the reactions was estimated from the equilibrium distribution of diastereomers. According to the results, the synthesis of bis-Betti bases is exothermic and accompanied by a decrease in entropy. The energy difference between the diastereomers is quite small, but the Gibbs free energy change for the equilibrium syn \( \rightleftharpoons \) anti favors the anti over syn configuration. These results are in good agreement with experimental observations.

Calculated and experimental IR spectrum for bis-Betti base 2 (mixture of anti and syn configurations)

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Acknowledgment

The corresponding author would like to thank the research council of Damghan University for supporting this work.

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Authors and Affiliations

  1. School of Chemistry, Damghan University, Damghan, 36716-41167, Iran

    Mehdi Zamani

  2. Department of Chemistry, Malek-ashtar University of Technology, Shahin-shahr, 83145/115, Iran

    Mehdi Shafiee & Mohammad Hossein Keshavarz

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  1. Mehdi Zamani
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  2. Mehdi Shafiee
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  3. Mohammad Hossein Keshavarz
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Correspondence to Mehdi Zamani.

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Zamani, M., Shafiee, M. & Keshavarz, M.H. Stereochemistry and spectroscopic analysis of bis-Betti base derivatives of 2,3-dihydroxynaphthalene. J Mol Model 22, 86 (2016). https://doi.org/10.1007/s00894-016-2936-x

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  • DOI: https://doi.org/10.1007/s00894-016-2936-x

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