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苯环:自组织系统中的空间位阻还是不同氢键模式的来源?

Phenyl Ring: A Steric Hindrance or a Source of Different Hydrogen Bonding Patterns in Self-Organizing Systems?

作者信息

Nowok Andrzej, Dulski Mateusz, Grelska Joanna, Szeremeta Anna Z, Jurkiewicz Karolina, Grzybowska Katarzyna, Musiał Małgorzata, Pawlus Sebastian

机构信息

Institute of Physics, University of Silesia in Katowice, 75 Pułku Piechoty 1, 41-500 Chorzów, Poland.

Silesian Center for Education and Interdisciplinary Research, 75 Pułku Piechoty 1A, 41-500 Chorzów, Poland.

出版信息

J Phys Chem Lett. 2021 Mar 4;12(8):2142-2147. doi: 10.1021/acs.jpclett.1c00186. Epub 2021 Feb 24.

DOI:10.1021/acs.jpclett.1c00186
PMID:33625856
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8034769/
Abstract

A series of five alcohols (3-methyl-2-butanol, 1-cyclopropylethanol, 1-cyclopentylethanol, 1-cyclohexylethanol, and 1-phenylethanol) was used to study the impact of the size of steric hindrance and its aromaticity on self-assembling phenomena in the liquid phase. In this Letter, we have explicitly shown that the phenyl ring exerts a much stronger effect on the self-organization of molecules via the O-H···O scheme than any other type of steric hindrance, leading to a significant decline in the size and concentration of the H-bonded clusters. Given the combination of calorimetric, dielectric, infrared, and diffraction studies, this phenomenon was ascribed to its additional proton-acceptor function for the competitive intermolecular O-H···π interactions. The consequence of this is a different packing of molecules on the short- and medium-range scale.

摘要

使用一系列五种醇(3-甲基-2-丁醇、1-环丙基乙醇、1-环戊基乙醇、1-环己基乙醇和1-苯乙醇)来研究空间位阻大小及其芳香性对液相中自组装现象的影响。在本信函中,我们明确表明,苯环通过O-H···O方案对分子自组织的影响比任何其他类型的空间位阻都要强得多,导致氢键簇的大小和浓度显著下降。考虑到量热、介电、红外和衍射研究的综合结果,这种现象归因于其对竞争性分子间O-H···π相互作用的额外质子受体功能。其结果是分子在短程和中程尺度上的堆积方式不同。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/00ca/8034769/03f18ec512f3/jz1c00186_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/00ca/8034769/ae80af36a46c/jz1c00186_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/00ca/8034769/428f9ac00a20/jz1c00186_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/00ca/8034769/6d94c7adc088/jz1c00186_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/00ca/8034769/03f18ec512f3/jz1c00186_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/00ca/8034769/ae80af36a46c/jz1c00186_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/00ca/8034769/428f9ac00a20/jz1c00186_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/00ca/8034769/6d94c7adc088/jz1c00186_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/00ca/8034769/03f18ec512f3/jz1c00186_0004.jpg

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