Two Isostructural Explosive Cocrystals with Significantly Different Thermodynamic Stabilities

Landenberger, Kira B.; Bolton, Onas; Matzger, Adam J.

doi:10.1002/anie.201302814

Cited by 173 publications

(122 citation statements)

References 37 publications

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“…Co-crystals [1][2][3][4][5][6] have been the subject of intense research in the last decade, due to their great potential for practical applications in several domains, 7,8 especially when active pharmaceutical ingredients, APIs, are concerned 5,9,10 . Pharmaceutical co-crystals, combining an API and an acceptable co-former, 11 have the potential for enhancing the physical properties of the API, positively impacting its solubility, stability, oral bioavailability and processability, without compromising its biological function 1,9,[12][13][14][15][16][17][18][19][20][21] .…”

Section: Introductionmentioning

confidence: 99%

Co-crystals of diflunisal and isomeric pyridinecarboxamides – a thermodynamics and crystal engineering contribution

et al. 2016

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This version is available at https://strathprints.strath.ac.uk/56947/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output.1 To whom correspondence should be addressed. E-mail: antonio.evora@uc.pt Tel.: Co-crystals of diflunisal and isomeric pyridinecarboxamides a thermodynamics and crystal engineering contribution +351239854450 ABSTRACTDiflunisal is an anti-inflammatory non-steroidal drug, class II of the Biopharmaceutical Classification System, that has recently been the subject of renewed interest due to its potential use in the oral therapy of familial amyloid polyneuropathy. In this work, a thermodynamic based approach is used to investigate binary mixtures (diflunisal + picolinamide) and (diflunisal + isonicotinamide) in order to identify solid forms potentially useful to improve the biopharmaceutical performance of this active pharmaceutical ingredient.Special emphasis is put on the research of co-crystals and on the influence of structural changes in the pyridinecarboxamide co-former molecules on co-crystal formation with diflunisal. The thermodynamic based methodology described by ter Horst et al. in 2010 indicates that the formation of co-crystals is thermodynamically feasible for both systems. The binary solid-liquid phase diagrams are built and allow identifying unequivocally the formation of co-crystals of diflunisal with each of the two isomers and also their stoichiometry: 1:1, (diflunisal:co-former) in the case of pyridine-2-carboxamide, picolinamide, and 2

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Section: Introductionmentioning

confidence: 99%

Co-crystals of diflunisal and isomeric pyridinecarboxamides – a thermodynamics and crystal engineering contribution

et al. 2016

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“…However, it is too sensitive to mechanical stimuli (impact or friction) and shock wave to meet the stringent safety requirements for modern weapons, consequently hampering its further applications [16][17] . Fortunately, Matzger and Millar research groups analyzed the intermolecular interactions of the structures of cocrystals, offering some insights into designing energetic cocrystals 10,[19][20][21] . Additionally, the O atom in carbonyl groups and water molecules is one of the stronger hydrogen bond acceptor, which readily 4 forms a hydrogen bond with a weak donor.…”

Section: Introductionmentioning

confidence: 99%

Cocrystal explosive hydrate of a powerful explosive, HNIW, with enhanced safety

et al. 2014

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A novel cocrystal explosive hydrate containing HNIW (hexanitrohexaazaisowurtzitane), NMP (N-methyl-2-pyrrolidone) and water was synthesized through cocrystallization. The crystal structure was characterized by power x-ray diffraction (PXRD) and single crystal x-ray diffraction (SXRD). This crystalline belongs to the monoclinic crystal system with space group P2(1)/c. The properties of cocrystal hydrate including thermal behavior, impact sensitivity and detonation performance were also evaluated. The cocrystal hydrate shows a unique thermal behavior with an endothermic peak and a decomposition peak at 91 and 252 ℃，respectively. Besides, the cocrystal hydrate displays an impact height with 50% ignition probability of 112 cm, indicating a substantial reduction in impact sensitivity compared to pure α-HNIW and ε-HNIW. Furthermore, although the power is diluted, the cocrystal hydrate is predicted to have more excellent detonation performances than pure DNAN (2,4-dinitroanisole) and TNT (trinitrotoluene). Therefore, the cocrystal hydrate may be a promising low sensitivity explosive. 5 reagents were purchased from trade and used as received. Synthesis of the HNIW/NMP/H2O cocrystal explosive hydrateε-HNIW (438 mg, 1 mmol) was added to a mixture of 2 ml of NMP and 0.5 ml of water, mildly heated to all ε-HNIW dissolution. The solution was allowed to evaporate slowly at room temperature over several days. The colorless cocrystal hydrates were precipitated, filtered and dried under ambient conditions. Morphology characterizationThe morphologies of cocrystal hydrates, α-HNIW and ε-HNIW were carried out by a Zeiss axio scope A1 microscope. Power X-ray diffraction (PXRD)XRD data were collected on a Bruker D8 Advance diffractometer using Cu-Kα radiation (λ=1.54056 Å) at 35 kV and 40 mA. The samples were scanned within the scan range of 2θ=7.5° to 45° continuous san with a step size of 0.015° and a scan speed of 0.2 s per step. Moreover, the PXRD pattern of the cocrystal hydrate was simulated by its CIF file and Reflex Module in Materials Studio package with the same sets as experiment 22 . Single crystal X-ray diffraction (SXRD)Single crystal of suitable quality was chosen and purged with a cooled nitrogen gas stream at 293 K throughout the data collection. X-ray reflections were collected on a Xcalibur Eos CCD detector with graphite-monochromated Mo− Kα radiation (λ=0.71073 Å). Data were collected and processed using Olex2 software. Structure was solved by direct methods and SHELX was used for structure solution and least-squares refinement 23 .

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“…Consequently, it makes sense that productive avenues towards new and improved energetic materials may be found through the use of co-crystal technology (Anderson et al, 2014;Li et al, 2014), whereby an energetic material is combined with either an energetic or a non-energetic compound (Guo et al, 2013) via non-covalent interactions within a crystalline framework (Landenberger et al, 2013). All in all, a co-crystal version of an energetic material can, in certain circumstances, be more useful because of superior chemical stability and shelf-life even though it may have slightly lower energetic performance.…”

Section: Applications Of Co-crystals and Co-crystal Technologymentioning

confidence: 99%