Open Access
Molecules, volume 26, issue 11, pages 3444
A combined experimental and theoretical study of nitrofuran antibiotics: Crystal structures, dft computations, sublimation and solution thermodynamics
Publication type: Journal Article
Publication date: 2021-06-05
PubMed ID:
34198944
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
Single crystal of furazolidone (FZL) has been successfully obtained, and its crystal structure has been determined. Common and distinctive features of furazolidone and nitrofurantoin (NFT) crystal packing have been discussed. Combined use of QTAIMC and Hirshfeld surface analysis allowed characterizing the non-covalent interactions in both crystals. Thermophysical characteristics and decomposition of NFT and FZL have been studied by differential scanning calorimetry (DSC), thermogravimetric analysis (TG) and mass-spectrometry. The saturated vapor pressures of the compounds have been measured using the transpiration method, and the standard thermodynamic functions of sublimation were calculated. It was revealed that the sublimation enthalpy and Gibbs energy of NFT are both higher than those for FZL, but a gain in the crystal lattice energy of NFT is leveled by an entropy increase. The solubility processes of the studied compounds in buffer solutions with pH 2.0, 7.4 and in 1-octanol was investigated at four temperatures from 298.15 to 313.15 K by the saturation shake-flask method. The thermodynamic functions of the dissolution and solvation processes of the studied compounds have been calculated based on the experimental data. Due to the fact that NFT is unstable in buffer solutions and undergoes a solution-mediated transformation from an anhydrate form to monohydrate in the solid state, the thermophysical characteristics and dissolution thermodynamics of the monohydrate were also investigated. It was demonstrated that a combination of experimental and theoretical methods allows performing an in-depth study of the relationships between the molecular and crystal structure and pharmaceutically relevant properties of nitrofuran antibiotics.
Citations by journals
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International Journal of Molecular Sciences
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International Journal of Molecular Sciences
2 publications, 28.57%
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1 publication, 14.29%
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IFMBE Proceedings, 1, 14.29%
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1 publication, 14.29%
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1 publication, 14.29%
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Citations by publishers
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3
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
3 publications, 42.86%
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American Chemical Society (ACS)
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American Chemical Society (ACS)
2 publications, 28.57%
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American Institute of Physics (AIP)
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American Institute of Physics (AIP)
1 publication, 14.29%
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ifmbe proceedings
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ifmbe proceedings, 1, 14.29%
ifmbe proceedings
1 publication, 14.29%
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3
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Manin A. N. et al. A combined experimental and theoretical study of nitrofuran antibiotics: Crystal structures, dft computations, sublimation and solution thermodynamics // Molecules. 2021. Vol. 26. No. 11. p. 3444.
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Manin A. N., Drozd K. V., Voronin A., Churakov A. V., PERLOVICH G. L. A combined experimental and theoretical study of nitrofuran antibiotics: Crystal structures, dft computations, sublimation and solution thermodynamics // Molecules. 2021. Vol. 26. No. 11. p. 3444.
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TY - JOUR
DO - 10.3390/molecules26113444
UR - https://doi.org/10.3390%2Fmolecules26113444
TI - A combined experimental and theoretical study of nitrofuran antibiotics: Crystal structures, dft computations, sublimation and solution thermodynamics
T2 - Molecules
AU - Manin, Alex N.
AU - Drozd, Ksenia V
AU - PERLOVICH, GERMAN L.
AU - Voronin, Alexander
AU - Churakov, Andrei V.
PY - 2021
DA - 2021/06/05 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 3444
IS - 11
VL - 26
PMID - 34198944
SN - 1420-3049
ER -
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@article{2021_Manin,
author = {Alex N. Manin and Ksenia V Drozd and GERMAN L. PERLOVICH and Alexander Voronin and Andrei V. Churakov},
title = {A combined experimental and theoretical study of nitrofuran antibiotics: Crystal structures, dft computations, sublimation and solution thermodynamics},
journal = {Molecules},
year = {2021},
volume = {26},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {jun},
url = {https://doi.org/10.3390%2Fmolecules26113444},
number = {11},
pages = {3444},
doi = {10.3390/molecules26113444}
}
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MLA
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Manin, Alex N., et al. “A combined experimental and theoretical study of nitrofuran antibiotics: Crystal structures, dft computations, sublimation and solution thermodynamics.” Molecules, vol. 26, no. 11, Jun. 2021, p. 3444. https://doi.org/10.3390%2Fmolecules26113444.