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Dostęp zamkniętyDoxycycline hydrate and doxycycline hydrochloride dihydrate – crystal structure and charge density analysis
| dc.abstract.en | High-resolution low-temperature X-ray diffraction experiments for doxycycline monohydrate and hydrochloride dihydrate have been performed. Translation-Libration-Screw (TLS) analysis for both crystal forms as well as the data from neutron diffraction experiment for hydrochloride combined with the Hansen-Coppens formalism resulted in precise charge density distribution models for both the zwitterionic monohydrate and a protonated hydrochloride crystal forms. Their detailed topological analysis suggested that the electron structure of doxycycline's amide moiety undergoes significant changes during protonation due to formation of a very strong resonance-assisted hydrogen bond. A notably increased participation of amide nitrogen atom and hydrogen-accepting oxygen atom in the resonance upon doxycycline protonation was observed. A comparison of TLS- and neutron data-derived hydrogen parameters confirmed the experimental neutron data to be vital for proper description of intra- and inter-molecular interactions in this compound. Finally, calculated lattice and interaction energies quantified repulsive Dox-Dox interactions in the protonated crystal form of the antibiotic, relating with a good solubility of doxycycline hydrochloride relative to its hydrate. |
| dc.affiliation | Uniwersytet Warszawski |
| dc.contributor.author | Makal, Anna |
| dc.contributor.author | Woźniak, Krzysztof |
| dc.contributor.author | Tchoń, Daniel |
| dc.contributor.author | Gutmann, Matthias |
| dc.date.accessioned | 2024-01-24T22:13:18Z |
| dc.date.available | 2024-01-24T22:13:18Z |
| dc.date.issued | 2018 |
| dc.description.finance | Nie dotyczy |
| dc.description.number | 9-10 |
| dc.description.volume | 233 |
| dc.identifier.doi | 10.1515/ZKRI-2018-2058 |
| dc.identifier.uri | https://repozytorium.uw.edu.pl//handle/item/105289 |
| dc.language | eng |
| dc.pbn.affiliation | chemical sciences |
| dc.relation.ispartof | Zeitschrift fur Kristallographie - Crystalline Materials |
| dc.relation.pages | 649-661 |
| dc.rights | ClosedAccess |
| dc.sciencecloud | nosend |
| dc.subject.en | charge density |
| dc.subject.en | doxycycline |
| dc.subject.en | neutron diffraction |
| dc.subject.en | QTAIM analysis |
| dc.subject.en | theoretical calculations |
| dc.title | Doxycycline hydrate and doxycycline hydrochloride dihydrate – crystal structure and charge density analysis |
| dc.type | JournalArticle |
| dspace.entity.type | Publication |