title: Peculiar behavior of starch 2,3-dialdehyde towards sulfanilamide and sulfathiazole.
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.
authors: King 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. Electronic address: keshksherif@gmail.com.
authors: Sherif M A S
authors: SMAS
authors: Keshk
authors: King Khalid University, Unite of Science and Technology, Faculty of Science, Chemistry Department, P.O. Box 9004, Abha 61413, Saudi Arabia; Alexandria University, Faculty of Science, Chemistry Department, Alexandria, Egypt.
authors: Ahmed M
authors: AM
authors: Ramadan
authors: King Khalid University, Unite of Science and Technology, Faculty of Science, Chemistry Department, P.O. Box 9004, Abha 61413, Saudi Arabia.
authors: Abdullah G
authors: AG
authors: Al-Sehemi
authors: Faculty of Science, Physics Department, P.O. Box 9004, Abha 61413, Saudi Arabia.
authors: El Sayed
authors: ES
authors: Yousef
authors: King Khalid University, Unite of Science and Technology, Faculty of Science, Chemistry Department, P.O. Box 9004, Abha 61413, Saudi Arabia; Mansoura University, Faculty of Science,Chemistry Department, Mansoura, Egypt.
authors: Samir
authors: S
authors: Bondock
keywords: Aldehyde content; Dialdehyde starch; Periodate oxidation; Schiff’s bases; Sulfa drugs