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Sulfation of Diethylaminoethyl-Cellulose: QTAIM Topological Analysis and Experimental and DFT Studies of the Properties
ACS Omega ( IF 3.7 ) Pub Date : 2021-08-25 , DOI: 10.1021/acsomega.1c02570 Aleksandr Kazachenko 1, 2 , Feride Akman 3 , Mouna Medimagh 4 , Noureddine Issaoui 4 , Natalya Vasilieva 1, 2 , Yuriy N Malyar 1, 2 , Irina G Sudakova 1 , Anton Karacharov 1 , Angelina Miroshnikova 1, 2 , Omar Marzook Al-Dossary 5
ACS Omega ( IF 3.7 ) Pub Date : 2021-08-25 , DOI: 10.1021/acsomega.1c02570 Aleksandr Kazachenko 1, 2 , Feride Akman 3 , Mouna Medimagh 4 , Noureddine Issaoui 4 , Natalya Vasilieva 1, 2 , Yuriy N Malyar 1, 2 , Irina G Sudakova 1 , Anton Karacharov 1 , Angelina Miroshnikova 1, 2 , Omar Marzook Al-Dossary 5
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Sulfated cellulose derivatives are biologically active substances with anticoagulant properties. In this study, a new sulfated diethylaminoethyl (DEAE)-cellulose derivative has been obtained. The effect of a solvent on the sulfation process has been investigated. It is shown that 1,4-dioxane is the most effective solvent, which ensures the highest sulfur content in DEAE-cellulose sulfate under sulfamic acid sulfation. The processes of sulfamic acid sulfation in the presence of urea in 1,4-dioxane and in a deep eutectic solvent representing a mixture of sulfamic acid and urea have been compared. It is demonstrated that the use of 1,4-dioxane yields the sulfated product with a higher sulfur content. The obtained sulfated DEAE-cellulose derivatives have been analyzed by Fourier transform infrared spectroscopy, X-ray diffractometry, and scanning electron and atomic force microscopy, and the degree of their polymerization has been determined. The introduction of a sulfate group has been confirmed by the Fourier transform infrared spectroscopy data; the absorption bands corresponding to sulfate groups have been observed in the ranges of 1247–1256 and 809–816 cm–1. It is shown that the use of a deep eutectic solvent leads to the side carbamation reactions. Amorphization of DEAE-cellulose during sulfation has been demonstrated using X-ray diffractometry. The geometric structure of a molecule in the ground state has been calculated using the density functional theory with the B3LYP/6-31G(d, p) basis set. The reactive areas of DEAE-cellulose and its sulfated derivatives have been analyzed using molecular electrostatic potential maps. The thermodynamic parameters (heat capacity, entropy, and enthalpy) of the target sulfation products have been determined. The HOMO–LUMO energy gap, Mulliken atomic charges, and electron density topology of the title compound have been calculated within the atoms in molecule theory.
中文翻译：
二乙氨基乙基纤维素的硫酸化：QTAIM 拓扑分析以及性能的实验和 DFT 研究
硫酸化纤维素衍生物是具有抗凝血特性的生物活性物质。在这项研究中，获得了一种新的硫酸化二乙氨基乙基（DEAE）-纤维素衍生物。研究了溶剂对硫酸化过程的影响。结果表明，1,4-二恶烷是最有效的溶剂，保证了氨基磺酸硫酸化过程中DEAE-硫酸纤维素的硫含量最高。比较了在 1,4-二恶烷中和在代表氨基磺酸和尿素混合物的低共熔溶剂中存在尿素的情况下氨基磺酸硫酸化的过程。结果表明，使用1,4-二恶烷可得到具有较高硫含量的硫酸化产物。通过傅里叶变换红外光谱、X射线衍射、扫描电子和原子力显微镜对所得硫酸化DEAE-纤维素衍生物进行了分析，并测定了其聚合度。傅里叶变换红外光谱数据证实了硫酸基的引入；在 1247-1256 和 809-816 cm –1范围内观察到对应于硫酸根基团的吸收带。结果表明，使用低共熔溶剂会导致副氨基甲酸酯化反应。使用 X 射线衍射法证明了 DEAE-纤维素在硫酸化过程中的非晶化。使用密度泛函理论和 B3LYP/6-31G(d, p) 基组计算了基态分子的几何结构。使用分子静电势图分析了 DEAE-纤维素及其硫酸化衍生物的反应区域。目标硫酸盐化产物的热力学参数（热容、熵和焓）已确定。 标题化合物的 HOMO-LUMO 能隙、Mulliken 原子电荷和电子密度拓扑已在分子理论中的原子内计算。
更新日期：2021-09-07
中文翻译：
二乙氨基乙基纤维素的硫酸化：QTAIM 拓扑分析以及性能的实验和 DFT 研究
硫酸化纤维素衍生物是具有抗凝血特性的生物活性物质。在这项研究中，获得了一种新的硫酸化二乙氨基乙基（DEAE）-纤维素衍生物。研究了溶剂对硫酸化过程的影响。结果表明，1,4-二恶烷是最有效的溶剂，保证了氨基磺酸硫酸化过程中DEAE-硫酸纤维素的硫含量最高。比较了在 1,4-二恶烷中和在代表氨基磺酸和尿素混合物的低共熔溶剂中存在尿素的情况下氨基磺酸硫酸化的过程。结果表明，使用1,4-二恶烷可得到具有较高硫含量的硫酸化产物。通过傅里叶变换红外光谱、X射线衍射、扫描电子和原子力显微镜对所得硫酸化DEAE-纤维素衍生物进行了分析，并测定了其聚合度。傅里叶变换红外光谱数据证实了硫酸基的引入；在 1247-1256 和 809-816 cm –1范围内观察到对应于硫酸根基团的吸收带。结果表明，使用低共熔溶剂会导致副氨基甲酸酯化反应。使用 X 射线衍射法证明了 DEAE-纤维素在硫酸化过程中的非晶化。使用密度泛函理论和 B3LYP/6-31G(d, p) 基组计算了基态分子的几何结构。使用分子静电势图分析了 DEAE-纤维素及其硫酸化衍生物的反应区域。目标硫酸盐化产物的热力学参数（热容、熵和焓）已确定。 标题化合物的 HOMO-LUMO 能隙、Mulliken 原子电荷和电子密度拓扑已在分子理论中的原子内计算。
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