Department of Chemistry, Federal University of Lavras, P.O. Box 3037, Lavras, MG, 37200-900, Brazil.
J Mol Model. 2021 Mar 4;27(4):101. doi: 10.1007/s00894-021-04719-y.
Thiosemicarbazones (TSCs) encompasses a class of compounds relevant in the pharmacological context. Their specific applicability varies in function of the appropriated chemical modification and their binding to different transition metals. In the present work, we apply current standards functionals, B3LYP and B97D, with triple zeta basis set quality, 6-311++G(d,p), to investigate the relative stability of the various possible spatial arrangements for 2-acetylthiophene and 2-acetylthiophene-N1-phenyl thiosemicarbazones, denoted ATTSC and ATTSC-Ph, respectively. The relative stability of neutral and deprotonated species at ethanol described by an implicit solvent model was investigated. For ATTSC, the relative Gibbs energy changed significantly upon deprotonation, and for ATTSC-Ph, a novel global minimum was identified. Based on the present study, deprotonation determines population in condensed-media. Such information, valid for ATTSC and ATTSC-Ph, can be crucial in studying other thiosemicarbazones.
硫代氨基甲脒（TSCs）属于一类在药理学背景下具有重要意义的化合物。它们的特殊适用性取决于适当的化学修饰以及与不同过渡金属的结合。在本工作中，我们应用当前的标准函数，B3LYP 和 B97D，采用三重 zeta 基质量，6-311++G(d,p)，来研究 2-乙酰基噻吩和 2-乙酰基噻吩-N1-苯基硫代氨基甲脒（分别表示为 ATTSC 和 ATTSC-Ph）的各种可能空间排列的相对稳定性。通过隐式溶剂模型研究了中性和去质子化物种在乙醇中的相对吉布斯自由能。对于 ATTSC，去质子化后相对吉布斯自由能发生了显著变化，而对于 ATTSC-Ph，确定了一个新的全局最小值。基于本研究，去质子化决定了凝聚态介质中的种群。对于 ATTSC 和 ATTSC-Ph，这种信息在研究其他硫代氨基甲脒时可能至关重要。
