Synthesis, characterisation, and crystallographic studies of sulfathiazole salts and related species / Siti Aina Mardia Akhmad Aznan
Co-crystallisation of equimolar quantities of sulfathiazole (STL) with each of 1,4-diazabicyclo[2.2.2]octane (DABCO) and piperazine (PIP) resulted in facile formation of salts [DABCOH][STL_H] (1) and [PIPH][STL_H] (2), respectively. Crystallographic studies show the formation of aniline-N–H...O(sulf...
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| Format: | Thesis |
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2018
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| Online Access: | http://studentsrepo.um.edu.my/9379/ http://studentsrepo.um.edu.my/9379/1/Siti_Aina_Mardiah_Akhmad_Aznan.pdf http://studentsrepo.um.edu.my/9379/6/aina.pdf |
| _version_ | 1848773907113312256 |
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| author | Siti Aina Mardia , Akhmad Aznan |
| author_facet | Siti Aina Mardia , Akhmad Aznan |
| author_sort | Siti Aina Mardia , Akhmad Aznan |
| building | UM Research Repository |
| collection | Online Access |
| description | Co-crystallisation of equimolar quantities of sulfathiazole (STL) with each of 1,4-diazabicyclo[2.2.2]octane (DABCO) and piperazine (PIP) resulted in facile formation of salts [DABCOH][STL_H] (1) and [PIPH][STL_H] (2), respectively. Crystallographic studies show the formation of aniline-N–H...O(sulfonyl) hydrogen bonds between anions to form supramolecular undulating and zigzag layers, respectively, with the cations being connected to these by charge-assisted N–H...N(thioazole) interactions. The salts formations were confirmed by 1H NMR, IR, Raman spectroscopies, CHN elemental analysis, Single Crystal X-ray Diffraction (SCXRD), Powder X-ray Diffraction (PXRD) and Differential Scanning Calorimetry (DSC) as well as melting point. Solid state grinding competition experiments were monitored by PXRD. In a sequence of experiments where STL was co-ground with a molar equivalent of PIP and n equivalents of DABCO (with n increasing from 0.1 to 1.0 in 0.1 increments), formation of salt 1 was observed. In related experiments where salt 2 was ground with an equimolar amount of DABCO, substitution of PIPH+ by DABCOH+ was evident, i.e., postsynthetic metathesis had occurred to about 70% for dry grinding. Quantitative yields were obtained in the case of liquid-assisted grinding (LAG) with a few drops of ethanol after 1.4 equivalents of DABCO were added. These observations are primarily correlated with differences in aniline-N–H...O(sulfonyl) hydrogen bonding that sustain the layers. |
| first_indexed | 2025-11-14T13:49:52Z |
| format | Thesis |
| id | um-9379 |
| institution | University Malaya |
| institution_category | Local University |
| last_indexed | 2025-11-14T13:49:52Z |
| publishDate | 2018 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | um-93792021-06-30T17:34:36Z Synthesis, characterisation, and crystallographic studies of sulfathiazole salts and related species / Siti Aina Mardia Akhmad Aznan Siti Aina Mardia , Akhmad Aznan Q Science (General) QD Chemistry Co-crystallisation of equimolar quantities of sulfathiazole (STL) with each of 1,4-diazabicyclo[2.2.2]octane (DABCO) and piperazine (PIP) resulted in facile formation of salts [DABCOH][STL_H] (1) and [PIPH][STL_H] (2), respectively. Crystallographic studies show the formation of aniline-N–H...O(sulfonyl) hydrogen bonds between anions to form supramolecular undulating and zigzag layers, respectively, with the cations being connected to these by charge-assisted N–H...N(thioazole) interactions. The salts formations were confirmed by 1H NMR, IR, Raman spectroscopies, CHN elemental analysis, Single Crystal X-ray Diffraction (SCXRD), Powder X-ray Diffraction (PXRD) and Differential Scanning Calorimetry (DSC) as well as melting point. Solid state grinding competition experiments were monitored by PXRD. In a sequence of experiments where STL was co-ground with a molar equivalent of PIP and n equivalents of DABCO (with n increasing from 0.1 to 1.0 in 0.1 increments), formation of salt 1 was observed. In related experiments where salt 2 was ground with an equimolar amount of DABCO, substitution of PIPH+ by DABCOH+ was evident, i.e., postsynthetic metathesis had occurred to about 70% for dry grinding. Quantitative yields were obtained in the case of liquid-assisted grinding (LAG) with a few drops of ethanol after 1.4 equivalents of DABCO were added. These observations are primarily correlated with differences in aniline-N–H...O(sulfonyl) hydrogen bonding that sustain the layers. 2018-03 Thesis NonPeerReviewed application/pdf http://studentsrepo.um.edu.my/9379/1/Siti_Aina_Mardiah_Akhmad_Aznan.pdf application/pdf http://studentsrepo.um.edu.my/9379/6/aina.pdf Siti Aina Mardia , Akhmad Aznan (2018) Synthesis, characterisation, and crystallographic studies of sulfathiazole salts and related species / Siti Aina Mardia Akhmad Aznan. Masters thesis, University of Malaya. http://studentsrepo.um.edu.my/9379/ |
| spellingShingle | Q Science (General) QD Chemistry Siti Aina Mardia , Akhmad Aznan Synthesis, characterisation, and crystallographic studies of sulfathiazole salts and related species / Siti Aina Mardia Akhmad Aznan |
| title | Synthesis, characterisation, and crystallographic studies of sulfathiazole salts and related species / Siti Aina Mardia Akhmad Aznan |
| title_full | Synthesis, characterisation, and crystallographic studies of sulfathiazole salts and related species / Siti Aina Mardia Akhmad Aznan |
| title_fullStr | Synthesis, characterisation, and crystallographic studies of sulfathiazole salts and related species / Siti Aina Mardia Akhmad Aznan |
| title_full_unstemmed | Synthesis, characterisation, and crystallographic studies of sulfathiazole salts and related species / Siti Aina Mardia Akhmad Aznan |
| title_short | Synthesis, characterisation, and crystallographic studies of sulfathiazole salts and related species / Siti Aina Mardia Akhmad Aznan |
| title_sort | synthesis, characterisation, and crystallographic studies of sulfathiazole salts and related species / siti aina mardia akhmad aznan |
| topic | Q Science (General) QD Chemistry |
| url | http://studentsrepo.um.edu.my/9379/ http://studentsrepo.um.edu.my/9379/1/Siti_Aina_Mardiah_Akhmad_Aznan.pdf http://studentsrepo.um.edu.my/9379/6/aina.pdf |