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dc.contributor.authorShukla, A.*
dc.contributor.authorKhan, E.*
dc.contributor.authorAlsirawan, MHD Bashir*
dc.contributor.authorMandal, R.*
dc.contributor.authorTandon, P.*
dc.contributor.authorVangala, Venu R.*
dc.date.accessioned2019-05-03T14:48:49Z
dc.date.available2019-05-03T14:48:49Z
dc.date.issued2019-05-14
dc.identifier.citationShukla A, Khan E, Alsirawan MB et al (2019) Spectroscopic (FT-IR, FT-Raman, and 13C SS-NMR) and quantum chemical investigations to provide structural insights into nitrofurantoin–4-hydroxybenzoic acid cocrystals. New Journal of Chemistry. 43(18): 7136-7149.en_US
dc.identifier.urihttp://hdl.handle.net/10454/17019
dc.descriptionYesen_US
dc.description.abstractCocrystallization is an attractive approach to improving the physicochemical properties of active pharmaceutical ingredients (APIs), which have great potential in drug development. Accordingly, there is a growing need to understand the physicochemical changes that occur upon co-crystallisation. This work focuses on the combined use of spectroscopy and density functional theory (DFT) calculations to understand the molecular structure, hydrogen bond interactions and physicochemical properties of a pharmaceutical cocrystal. Solid-state NMR (ssNMR) spectroscopy can provide detailed molecular structure information on pharmaceutical cocrystals and complexes. It is non-destructive and usually provides deep structural insights that complement well with vibrational spectroscopy. In this work, a cocrystal of an antibiotic drug, nitrofurantoin (NF), with 4-hydroxybenzoic acid (4HBA) is examined to understand the capability of multiple spectroscopic techniques such as infrared (IR), Raman and solid-state NMR spectroscopies, and to confirm the molecular structure and hydrogen bonding of cocrystal systems. The results of IR and Raman spectroscopy showed that for the cocrystal formation, NF and 4HBA molecules interact through N–H⋯O–H interactions between the imide N–H of nitrofurantoin and the phenolic –OH of 4-hydroxybenzoic acid, and these interactions are also confirmed by natural bond orbital (NBO) and quantum theory of atoms in molecules (QTAIM) analyses. It is critical to understand whether a given cocrystal, upon conceiving a modified crystalline structure compared to that of its API, shows enhanced physical and chemical properties or not. Computationally, it is found that the NF–4HBA cocrystal shows softer (more reactive) behaviour in comparison to NF as its cocrystal, NF–4HBA, has a low band gap in comparison to the API, NF. These results demonstrate that the quantum chemical approach predicts accurately how to relate cocrystal with its physical and chemical properties.en_US
dc.description.sponsorshipBSR meritorious fellowship scheme. The Newton-Bhabha PhD placement award (2017). The Royal Society Seed Corn Research Grant (2018-19)en_US
dc.language.isoenen_US
dc.relation.isreferencedbyhttps://doi.org/10.1039/c8nj05946ben_US
dc.rights(c) 2019 Royal Society of Chemistry. Full-text reproduced in accordance with the publisher's self-archiving policy.en_US
dc.subjectCocrystallisationen_US
dc.subjectActive pharmaceutical ingredientsen_US
dc.subjectDrug developmenten_US
dc.subjectSpectroscopyen_US
dc.subjectDensity Functional Theoryen_US
dc.subjectDFTen_US
dc.titleSpectroscopic (FT-IR, FT-Raman, and 13C SS-NMR) and quantum chemical investigations to provide structural insights into nitrofurantoin–4-hydroxybenzoic acid cocrystalsen_US
dc.status.refereedYesen_US
dc.date.Accepted2019-04-12
dc.date.application2019-04-12
dc.typeArticleen_US
dc.date.EndofEmbargo2020-04-13
dc.type.versionAccepted manuscripten_US
dc.description.publicnotesThe full-text of this article will be released for public view at the end of the publisher embargo on 13 Apr 2020.en_US


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