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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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Main Author: Siti Aina Mardia , Akhmad Aznan
Format: Thesis
Published: 2018
Subjects:
Q Science (General)
QD Chemistry
Online Access:http://studentsrepo.um.edu.my/9379/1/Siti_Aina_Mardiah_Akhmad_Aznan.pdf
http://studentsrepo.um.edu.my/9379/6/aina.pdf
http://studentsrepo.um.edu.my/9379/
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spelling my.um.stud.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/
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Student Repository
url_provider http://studentsrepo.um.edu.my/
topic Q Science (General)
QD Chemistry
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
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.
format Thesis
author Siti Aina Mardia , Akhmad Aznan
author_facet Siti Aina Mardia , Akhmad Aznan
author_sort Siti Aina Mardia , Akhmad Aznan
title 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_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_sort synthesis, characterisation, and crystallographic studies of sulfathiazole salts and related species / siti aina mardia akhmad aznan
publishDate 2018
url http://studentsrepo.um.edu.my/9379/1/Siti_Aina_Mardiah_Akhmad_Aznan.pdf
http://studentsrepo.um.edu.my/9379/6/aina.pdf
http://studentsrepo.um.edu.my/9379/
_version_ 1738506258319671296
score 13.211869

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