双苯并咪唑衍生物与葫芦脲和环己基葫芦脲络合的计算研究

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2021-05-15 DOI:10.1007/s10847-021-01078-2
N. S. Venkataramanan, A. Suvitha, R. Sahara, Y. Kawazoe
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引用次数: 2

摘要

利用密度泛函理论研究了1,ω-双苯并咪唑衍生物与葫芦[6]脲(Q[6])和环己六葫芦[6]脲(Cy6Q[6])宿主在1:1化学计量下的结合特性。两个苯咪唑酸氢之间的距离以及柔性丁基间隔基团对与宿主络合起着至关重要的作用。能量分析表明,Q[6]的嘉宾比Cy6Q[6]的嘉宾络合能力强。计算得到的焓和自由能变化均为负,表明包封过程是自发的、热力学有利的、焓驱动的。基于全局反应性描述符的电荷转移计算表明,电子密度差图支持从客体分子到宿主分子的电荷转移。稳定配合物稳定性较高的主要因素是除了弱的C··O、C··N、N··O、C··H、H··N型相互作用外,还存在C - H··O=C的氢键相互作用。AIM拓扑参数和NCI分析揭示了弱相互作用的存在,本质上主要是静电相互作用,稳定配合物中存在较多的氢键。EDA分析表明,包封的配合物存在非共价和部分共价静电相互作用。与Q[6]相比,Cy6Q[6]配合物的稳定性较低,这是由于Cy6Q[6]宿主上存在正的v值,即环己酮亚甲基氢的最大值。图形抽象
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A computational study on the complexation of bisbenzimidazolyl derivatives with cucurbituril and cyclohexylcucurbituril

The binding properties of 1,ω-bisbenzimidazolyl derivatives with cucurbit[6]uril (Q[6]) and cyclohexanocucurbit[6]uril (Cy6Q[6]) host, for 1:1 stoichiometry, have been studied using density functional theory. The distance between the two benimidazole acidic hydrogen’s along with the flexible butyl spacer group play a vital role in the complexation with host. The energetic analysis exhibits strong complexation ability of guests with Q[6] than Cy6Q[6] host. The computed enthalpy and free energy change were negative indicating the encapsulation process to be spontaneous and thermodynamically favorable and enthalpy driven. The global reactivity descriptors based charge transfer calculations show that charge transfer occurs from the guest to host molecule which was supported by the electron density difference map. The main factors for the higher stability of stable complex was the presence of C–H····O=C hydrogen bonding interactions in addition to the weak C···O, C···N, N···O, C···H, H···N type of interactions. AIM topological parameters and NCI analysis reveals the existence of weak interaction, mainly of electrostatic in nature and more number of hydrogen bonds are present in stable complexes. EDA analysis demonstrates the presence of noncovalent and electrostatic interaction with partial covalent character in the encapsulated complexes. The lower stability of Cy6Q[6] complexes compare to Q[6] are due to the presence of positive Vs,max values of cyclohexanone methylene hydrogen’s on Cy6Q[6] host.

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来源期刊
Journal of Inclusion Phenomena and Macrocyclic Chemistry
Journal of Inclusion Phenomena and Macrocyclic Chemistry Agricultural and Biological Sciences-Food Science
CiteScore
4.10
自引率
8.70%
发文量
54
期刊介绍: The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites. The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.
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