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http://hdl.handle.net/10773/20857
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DC Field | Value | Language |
---|---|---|
dc.contributor.author | Martins, Ines C. B. | pt |
dc.contributor.author | Sardo, Mariana | pt |
dc.contributor.author | Santos, Sergio M. | pt |
dc.contributor.author | Femandes, Auguste | pt |
dc.contributor.author | Antunes, Alexandra | pt |
dc.contributor.author | Andre, Vania | pt |
dc.contributor.author | Mafra, Luis | pt |
dc.contributor.author | Teresa Duarte, M. | pt |
dc.date.accessioned | 2017-12-07T20:01:53Z | - |
dc.date.issued | 2016 | pt |
dc.identifier.issn | 1528-7483 | pt |
dc.identifier.uri | http://hdl.handle.net/10773/20857 | - |
dc.description.abstract | The reactivity of the active pharmaceutical ingredient azelaic acid (AA) with carboxylic acid, alcohol, amine, and amide based co-formers was screened. Five new multicomponent crystal forms of AA were obtained by liquid assisted grinding and conventional solution methods. The obtained forms: (i) a co-crystal with 4,4'-bipyridine (AA:BIP, 1), (ii) an anhydrous and an hydrated molecular salt with piperazine (AA:PIP, 2 and 3), and (iii) two anhydrous molecular salts with morpholine (AA:MORPH, 4) and 1,4-diazobicyclo[2.2.2]octane (AA:DABCO, 5), were fully characterized by X-ray diffraction and solid-state (SS) NMR. In all new forms the carboxylic-carboxylic R-2(2)(8) homosynthon present in AA is broken, and NH2 center dot center dot center dot O-COOH or +NH2 center dot center dot center dot O-COO-hydrogen bonds (HBs) become the fundamental pillars in the new supramolecular arrangements. The X-ray structure of 4 exhibits a static disorder in the hydrogen atoms engaged in an HB between two COOH moieties of AA. Density functional theory geometry optimization of the hydrogen positions followed by GIPAW-DFT calculations of H-1 chemical shifts showed that such disordered atoms refer to O center dot center dot center dot H center dot center dot center dot O hydrogens, roughly equidistant from both proton acceptor and donor atoms. SSNMR detected unusually strong HBs associated with such disordered hydrogens through the presence of H-1 resonances shifted to very high frequencies (up to ca. 20.1 ppm). These results clearly show the advantageous use of both X-ray diffraction and SSNMR techniques for structural elucidation. We concluded that the hydrated piperazine salt 3 readily converted to 2 at ambient RH and that their thermal behavior is strongly determined by both the supramolecular arrangement and strength of HB network. Piperazine salt 2 presents an improved aqueous solubility bestowing a promising opportunity to avoid the use of alcoholic solutions in the final formulations. | pt |
dc.language.iso | eng | pt |
dc.publisher | AMER CHEMICAL SOC | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/3599-PPCDT/122447/PT | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F78854%2F2011/PT | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F65978%2F2009/PT | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F64752%2F2009/PT | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/5876-PPCDTI/135103/PT | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/5876/147216/PT | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/5876/147332/PT | pt |
dc.rights | restrictedAccess | por |
dc.subject | VARIABLE CHAIN-LENGTH | pt |
dc.subject | CO-CRYSTALS | pt |
dc.subject | DICARBOXYLIC-ACIDS | pt |
dc.subject | COCRYSTALS | pt |
dc.subject | CRYSTALLOGRAPHY | pt |
dc.subject | CARBOXYLATES | pt |
dc.subject | DIFFRACTION | pt |
dc.subject | SOLUBILITY | pt |
dc.subject | MECHANISM | pt |
dc.subject | ADDUCTS | pt |
dc.title | Packing Interactions and Physicochemical Properties of Novel Multicomponent Crystal Forms of the Anti-Inflammatory Azelaic Acid Studied by X-ray and Solid-State NMR | pt |
dc.type | article | pt |
dc.peerreviewed | yes | pt |
ua.distribution | international | pt |
degois.publication.firstPage | 154 | pt |
degois.publication.issue | 1 | pt |
degois.publication.lastPage | 166 | pt |
degois.publication.title | CRYSTAL GROWTH & DESIGN | pt |
degois.publication.volume | 16 | pt |
dc.date.embargo | 10000-01-01 | - |
dc.relation.publisherversion | 10.1021/acs.cgd.5b01057 | pt |
dc.identifier.doi | 10.1021/acs.cgd.5b01057 | pt |
Appears in Collections: | CICECO - Artigos |
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