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Synthesis and structural study of 2-(haloalkyl)-3-methylchromones

Monatshefte für Chemie - Chemical Monthly volume 150, pages 1929–1940 (2019)Cite this article

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Abstract

The novel 2-(difluoromethyl)-3-methylchromone, 2-(dichloromethyl)-3-methylchromone, and 3-methyl-2-(perfluoroethyl)chromone were synthesized by a one-pot method and characterized through MS spectrometry, cyclic voltammetry, and vibrational (IR, Raman), UV–Vis, fluorescence, and NMR (1H, 13C, and 19F) spectroscopy. The crystal structure of 2-(difluoromethyl)-3-methylchromone and 2-(dichloromethyl)-3-methylchromone determined by X-ray diffraction methods were used to calculate their intermolecular interactions and crystal lattice energies together with the Hirshfeld surface analysis.

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Acknowledgements

The authors thank Universidad Nacional de La Plata (UNLP), CONICET, Departamento de Ciencias Básicas de la Universidad Nacional de Luján (Argentina) and DAAD (Germany) for financial support. S.E.U and J.L.J specially thanks Deutscher Akademischer Austauschdienst (DAAD) for an equipment grant and financial support. CDAL thanks SENESCYT for the fellowship and financial support. This work was supported by UNLP (11/X830 and 11/X848), CONICET (PIP: 0359 and 1529), and by ANPCyT (PME06 2804 and PICT06 2315) of Argentina. S.E.U., G.A.E., and O.E.P, are Research Fellows of CONICET; J.L.J. is a Researcher of Comisión de Investigaciones Científicas de la Provincia de Buenos Aires (CICPBA), Argentina.

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Authors and Affiliations

  1. Centro de Investigación de Alimentos, CIAL, Facultad de Ciencias de la Ingeniería e Industrias, Universidad UTE, EC171029, Quito, Ecuador

    Christian D. Alcívar León & Luis A. Ramos Guerrero

  2. Facultad de Ciencias Químicas, Universidad Central del Ecuador, Francisco Viteri y Gilberto Sobral s/n, Ciudad Universitaria, Quito, Ecuador

    Pablo M. Bonilla Valladares

  3. Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata e IFLP (CONICET, CCT-La Plata), C. C. 67, 1900, La Plata, Argentina

    Gustavo A. Echeverría & Oscar E. Piro

  4. CEQUINOR (CONICET-UNLP), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 e/60 y 64 Nº 1465, 1900, La Plata, Argentina

    Sonia E. Ulic

  5. Departamento de Ciencias Básicas, Universidad Nacional de Luján, Rutas 5 y 7, Luján, 6700, Buenos Aires, Argentina

    Sonia E. Ulic

  6. UPL (UNIDAD PLAPIMU-LASEISIC, UNLP-CIC), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 esq. 115, 1900, La Plata, Argentina

    Jorge L. Jios

  7. Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059, Rostock, Germany

    Peter Langer

  8. Leibniz Institut für Katalyse, Universität Rostock e. V. (LIKAT), Albert-Einstein-Str. 29a, 18059, Rostock, Germany

    Peter Langer

Authors
  1. Christian D. Alcívar León
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  2. Luis A. Ramos Guerrero
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  3. Pablo M. Bonilla Valladares
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  4. Gustavo A. Echeverría
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  5. Oscar E. Piro
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  6. Sonia E. Ulic
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  7. Jorge L. Jios
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  8. Peter Langer
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Correspondence to Sonia E. Ulic or Jorge L. Jios.

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Alcívar León, C.D., Ramos Guerrero, L.A., Bonilla Valladares, P.M. et al. Synthesis and structural study of 2-(haloalkyl)-3-methylchromones. Monatsh Chem 150, 1929–1940 (2019). https://doi.org/10.1007/s00706-019-02512-5

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  • DOI: https://doi.org/10.1007/s00706-019-02512-5

Keywords

  • Haloalkylchromones
  • Spectroscopic properties
  • Single crystal X-ray diffraction
  • Quantum chemical calculations
  • Hirshfeld surface analysis