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Peculiar behavior of starch 2,3-dialdehyde towards sulfanilamide and sulfathiazole
Sherif M A S Keshk1, Ahmed M Ramadan2, Abdullah G Al-Sehemi3
1King Khalid University, Unite of Science and Technology, Faculty of Science, Chemistry Department, P.O. Box 9004, Abha 61413, Saudi Arabia; Ain Shams University, Institute of Environmental Studies and Research, Basic Science Department, Abbassia, Cairo 11566, Egypt.
Abstract:
In this study, starch (1) was oxidized to starch-2,3-dialdehyde (DAS; 2) using potassium periodate. In addition, two novel Schiff's bases (5 &6) were synthesized via a condensation reaction between DAS (2) and sulfa drugs (sulfanilamide; 3 & sulfathiazole; 4). The synthesized Schiff's bases (5 &6) were characterized by FT-IR spectroscopy, X-ray diffraction and DSC analysis. DAS can easily be oxidized owing to its high aldehyde content (91.0%). However, it has low reactivity towards sulfanilamide (3) and sulfathiazole (4). According to the diffraction functional theory, this peculiar behavior is caused by the absence of V-shape in α-glucan linkage in DAS molecules, making the carbonyl group least electropositive. This reduces the nucleophilic attacks of the amino group in sulfa drugs towards the carbonyl group in DAS.
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