Investigation of the hydrogen bonded host‧‧‧guest and guest‧‧‧guest interactions present in complexes of a polyaromatic wheel-and-axle host compound with dioxane, morpholine, piperidine and pyridine

IF 2.3 4区 化学 Q2 Agricultural and Biological Sciences Journal of Inclusion Phenomena and Macrocyclic Chemistry Pub Date : 2023-11-21 DOI:10.1007/s10847-023-01210-4
Benita Barton, Mino R. Caira, Jarryd Vorgers, Eric C. Hosten
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Abstract

1,4-Bis(diphenylhydroxymethyl)benzene (H), a host compound possessing wheel-and-axle geometry, was found to possess host ability for dioxane (DIO), morpholine (MOR) and piperidine (PIP), forming inclusion compounds with each one with 1:2 host:guest ratios. This observation prompted an investigation of the host behaviour in mixtures of these guest compounds but where pyridine (PYR) was also considered (PYR was reported earlier to also form a 1:2 complex with H). In mixtures, H demonstrated significant affinities for, more especially, MOR and PIP, while DIO and PYR were usually disfavoured guest species. Single crystal X-ray diffraction experiments revealed that MOR (a favoured guest species) interacted by means of three hydrogen bonds with both adjacent guest and host molecules, plausibly explaining the host preference for this guest species; each of DIO, PYR and PIP were involved in only one interaction of this type with H. Total energy calculations revealed that the host-guest molecular pairs involving preferred MOR and PIP possessed significantly lower energies than those with disfavoured DIO and PYR. Thermal analyses demonstrated that the complex containing the least favoured guest compound, H‧2(DIO), possessed the lowest thermal stability of the four complexes, but these experiments did not clearly explain the affinity of H for MOR.

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多芳轮轴主化合物与二恶烷、啉、哌啶和吡啶配合物中氢键主-客体和客体-客体相互作用的研究
1,4-二(二苯基羟基甲基)苯(H)是一种具有轮轴几何结构的寄主化合物,对二氧六环(DIO)、啉(MOR)和哌啶(PIP)具有寄主能力,形成包涵体,每一包涵体的主客体比为1:2。这一观察结果促使了对这些客体化合物混合物中宿主行为的调查,其中也考虑了吡啶(PYR)(早先报道PYR也与H形成1:2的配合物)。在混合物中,H尤其对MOR和PIP表现出显著的亲和力,而DIO和PYR通常是不受欢迎的客体物种。单晶x射线衍射实验表明,MOR(一种受欢迎的客体物质)通过三个氢键与相邻的客体和宿主分子相互作用,合理地解释了宿主对该客体物质的偏好;总能量计算表明,DIO、PYR和PIP均只与h发生一次这种类型的相互作用,而含有MOR和PIP的主客体分子对的能量显著低于含有DIO和PYR的主客体分子对。热分析表明,含最不利客体化合物H·2(DIO)的配合物具有最低的热稳定性,但这些实验并不能清楚地解释H对MOR的亲和力。
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来源期刊
CiteScore
3.30
自引率
8.70%
发文量
0
审稿时长
3-8 weeks
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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