Single crystal XRD, vibrational and quantum chemical calculation of pharmaceutical drug paracetamol: A new synthesis form

Anitha, R.; Gunasekaran, M.; Kumar, Sandeep; Athimoolam, S.; Sridhar, Balasubramanian

doi:10.1016/j.saa.2015.05.091

Cited by 9 publications

(4 citation statements)

References 31 publications

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“…Anitha and co-workers , reported the assignment of spectral bands for paracetamol, while Vijayalakshmi et al reported the assignment of the Raman bands for 4-nitrophenol. Characteristic 4-nitrophenol Raman peaks were 303, 869, 1110, 1586, and 3085 cm –1 .…”

Section: Resultsmentioning

confidence: 99%

Impact of Paracetamol Impurities on Face Properties: Investigating the Surface of Single Crystals Using TOF-SIMS

Ottoboni

Chrubasik

Bruce

et al. 2018

Crystal Growth & Design

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Understanding the mechanism of interaction between pharmaceutical molecules (APIs) and impurities on crystal surfaces is a key concept in understanding purification and for the design of pharmaceutical crystallization processes. Several techniques may be used to study crystal surface properties, such as scanning electron microscopy (SEM) and X-ray photoelectron spectroscopy (XPS), which provide detailed imaging and elemental surface characterization. Time of flight secondary ion mass spectrometry (TOF-SIMS) is valuable in determining molecular identity and distribution. By combining TOF-SIMS, SEM, and optical (OM) and Raman microscopies, we can evaluate the usefulness of TOF-SIMS as a surface characterization technique for pharmaceutical crystals. 4-Nitrophenol has been selected as an impurity that can be incorporated during crystallization of acetaminophen (paracetamol). This study explores the distribution of impurity and its concentration on the different crystal faces of samples obtained by crystallization over a range of impurity loadings and supersaturation conditions. Raman maps of paracetamol single crystal faces were analyzed using the characteristic Raman peak intensity of 4-nitrophenol to identify regions where it accumulated; Raman maps of three single crystals produced in the presence of 4-nitrophenol using different crystallization procedures highlight how it can be difficult to detect very low concentrations of similar chemical species. In contrast, the 4-nitrophenol monoisotopic mass obtained via TOF-SIMS was shown to be detectable in all the three single crystals produced. This indicates that TOF-SIMS can be a valuable technique for single crystal impurity distribution mapping even when the impurity concentration is very low.

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Section: Resultsmentioning

confidence: 99%

Impact of Paracetamol Impurities on Face Properties: Investigating the Surface of Single Crystals Using TOF-SIMS

Ottoboni

Chrubasik

Bruce

et al. 2018

Crystal Growth & Design

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“…Unfortunately under our hands, benzoic acid and paracetamol only gave separate crystals. Among the different cocrystals obtained from paracetamol in the literature, a cocrystal was obtained in a 2/1 molar ratio of paracetamol to citric acid. This is in agreement with the value obtained from XPS on the polycarboxyphenyl films trapping paracetamol.…”

Section: Results and Discussionmentioning

confidence: 99%

Reversible Trapping of Functional Molecules at Interfaces Using Diazonium Salts Chemistry

et al. 2016

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Developing thin polymeric films for trapping, releasing, delivering, and sensing molecules is important for many applications in chemistry, biotechnology, and environment. Hence, a facile and scalable technique for loading specific molecules on surfaces would rapidly translate into applications. This work presents a novel method for the trapping of functional molecules at interfaces by exploiting diazonium salt chemistry. We demonstrate the efficiency of this approach by trapping two different molecules, 4-nitrobenzophenone and paracetamol, within polycarboxyphenyl layers grafted on gold and glassy carbon (GC) and by releasing them in acidic medium. The former molecule was chosen as a proof of concept for its electrochemical and spectroscopic properties, and the latter one was selected as an example of a pharmaceutical molecule. Advantages of the present approach rely on the simplicity, rapidity, and efficiency of the procedure for the reversible, on demand, trapping and release of functional molecules.

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“…The OH⋅⋅⋅O‐based supramolecular chain is a typical motif also seen in para‐ and metacetamol . In all three paracetamol polymorphs, however, NH⋅⋅⋅OH interactions are also present and laterally connect adjacent chains to form 2D sheets –. Spirally arranged NH⋅⋅⋅OH interactions are instead responsible for the formation of a 3D supramolecular network in the orthorhombic polymorph of metacetamol …”

Section: Figurementioning

confidence: 87%

The Crystal Structure of Orthocetamol Solved by 3D Electron Diffraction

et al. 2019

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Single crystal XRD, vibrational and quantum chemical calculation of pharmaceutical drug paracetamol: A new synthesis form

Cited by 9 publications

References 31 publications

Impact of Paracetamol Impurities on Face Properties: Investigating the Surface of Single Crystals Using TOF-SIMS

Impact of Paracetamol Impurities on Face Properties: Investigating the Surface of Single Crystals Using TOF-SIMS

Reversible Trapping of Functional Molecules at Interfaces Using Diazonium Salts Chemistry

The Crystal Structure of Orthocetamol Solved by 3D Electron Diffraction

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