Inclusion of thymol into cucurbiturils: density functional theory approach with dispersion correction and natural bond orbital analysis

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2022-03-25 DOI:10.1007/s10847-022-01135-4

Kye-Ryong Sin, Chol-Jin Kim, Sun-Gyong Ko, Tok-Man Hwang, Yong-Nam Han, Yong-Nam Pak

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引用次数: 3

Abstract

Stability of inclusion complexes of thymol (a natural flavour) with cucurbit[n]urils was interpreted by using density functional theory with dispersion correction and natural bond orbital analysis. Density functional tight binding computations showed that among different cucurbit[n = 5–8]urils, some inverted diastereoisomers of cucurbit[7]uril can form relatively stable inclusion complexes with thymol in water. From density functional theory computations, it can be seen that non-covalent interaction and electron transfer between thymol and CB[7] offer more stability to the inclusion complex. Theoretically calculated dipole moments and electronic spectra of thymol and the its inclusion complex showed that the inclusion complex can have better solubility and photo-resistance than free thymol.

Graphical abstract

Thymol inclusion into CB[n]: Inclusion of thymol into cucurbit[n]urils (CB[n]) was studied by DFTB + and DFT computations. The doubly-inverted CB[7] (i2-CB[7]) can form more stable inclusion complex (thymol@i2-CB[7]) with thymol than other CB[n].(see figure)

Abstract Image

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百里香酚在瓜脲中的包合:密度泛函理论方法及色散校正和自然键轨道分析

采用密度泛函理论，结合色散校正和天然键轨道分析，对天然香精百里香与瓜蕊包合物的稳定性进行了分析。密度泛函数紧密结合计算表明，在不同的葫芦[n = 5-8]uril中，葫芦[7]uril的一些反向非对映异构体可以与百里酚在水中形成相对稳定的包合物。从密度泛函理论计算可以看出，百里香酚与CB之间的非共价相互作用和电子转移[7]使包合物更加稳定。理论计算的百里香酚及其包合物的偶极矩和电子能谱表明，包合物比游离百里香酚具有更好的溶解度和抗光性。图abstract百里香酚包合CB[n]:通过DFTB +和DFT计算，研究了百里香酚包合葫芦[n]香蕊(CB[n])。双倒置CB[7] (i2-CB[7])与百里酚形成的包合物(thymol@i2-CB[7])比其他CB[n]更稳定。(见图)

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来源期刊

Journal of Inclusion Phenomena and Macrocyclic Chemistry Agricultural and Biological Sciences-Food Science

CiteScore

4.10

自引率

8.70%

发文量

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.