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取代蒽酚衍生物中的经典和反向取代基效应

Classical and Reverse Substituent Effects in Substituted Anthrol Derivatives.

作者信息

Szatylowicz Halina, Domanski Mateusz A, Krygowski Tadeusz M

机构信息

Faculty of Chemistry Warsaw University of Technology Noakowskiego 3 00-664 Warsaw Poland.

Department of Chemistry Warsaw University Pasteura 1 02-093 Warsaw Poland.

出版信息

ChemistryOpen. 2019 Jan 25;8(1):64-73. doi: 10.1002/open.201800234. eCollection 2019 Jan.

DOI:10.1002/open.201800234
PMID:30697512
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6346296/
Abstract

The substituent effect in 1-, 2-, and 9-anthrols is studied by means of B3LYP/6-311++G(d,p) computation, taking into account substituents (X): NO, CN, OH and NH located in all positions except the adjacent ones. The substituent effect is characterized by approaches based on quantum chemistry: The charge of the substituent active region (cSAR), substituent effect stabilization energy (SESE) and the charge flow index (CFI) describing flow of the charge from X to the fixed group (or vice versa) as well as substituent constants . Changes in properties observed in the fixed group (OH) are described by cSAR(OH). Mutual interdependences are found between these descriptors. The HOMA index is used to describe an effect of a substituent on aromaticity of an anthrol hydrocarbon skeleton and of individual rings. In all cases, the classical (influence of X on the properties of OH) and reverse (influence of OH on the properties of X) substituent effects are studied. The latter is clearly documented by the cSAR approach.

摘要

采用B3LYP/6-311++G(d,p)计算方法，研究了1-、2-和9-蒽酚中的取代基效应，其中考虑了位于除相邻位置外所有位置的取代基（X）：NO、CN、OH和NH。取代基效应通过基于量子化学的方法来表征：取代基活性区域的电荷（cSAR）、取代基效应稳定能（SESE）以及描述电荷从X流向固定基团（或反之亦然）的电荷流动指数（CFI）以及取代基常数。固定基团（OH）中观察到的性质变化用cSAR(OH)来描述。发现这些描述符之间存在相互依存关系。HOMA指数用于描述取代基对蒽酚烃骨架和各个环的芳香性的影响。在所有情况下，都研究了经典的（X对OH性质的影响）和反向的（OH对X性质的影响）取代基效应。后者通过cSAR方法得到了明确的证明。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/6330a27f8a37/OPEN-8-64-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/a77d17f455ff/OPEN-8-64-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/b81c5c517edc/OPEN-8-64-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/cd70d1f650f4/OPEN-8-64-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/5d82227dbb8a/OPEN-8-64-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/84040231ab38/OPEN-8-64-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/6cdd5e02dada/OPEN-8-64-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/6330a27f8a37/OPEN-8-64-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/a77d17f455ff/OPEN-8-64-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/b81c5c517edc/OPEN-8-64-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/cd70d1f650f4/OPEN-8-64-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/5d82227dbb8a/OPEN-8-64-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/84040231ab38/OPEN-8-64-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/6cdd5e02dada/OPEN-8-64-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2cfa/6346296/6330a27f8a37/OPEN-8-64-g007.jpg

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本文引用的文献

1
Toward the Physical Interpretation of Inductive and Resonance Substituent Effects and Reexamination Based on Quantum Chemical Modeling.基于量子化学建模对诱导效应和共振取代基效应的物理解释及重新审视
ACS Omega. 2017 Oct 26;2(10):7163-7171. doi: 10.1021/acsomega.7b01043. eCollection 2017 Oct 31.
2
Towards physical interpretation of substituent effects: the case of meta- and para-substituted anilines.迈向取代基效应的物理解释：间位和对位取代苯胺的情况
Phys Chem Chem Phys. 2016 Apr 28;18(17):11711-21. doi: 10.1039/c5cp06702b.
3
Toward a physical interpretation of substituent effects: the case of fluorine and trifluoromethyl groups.
走向取代基效应的物理解释：氟和三氟甲基的例子。
J Org Chem. 2014 Aug 15;79(16):7321-31. doi: 10.1021/jo501013p. Epub 2014 Jul 29.
4
Energetic aspects of cyclic pi-electron delocalization: evaluation of the methods of estimating aromatic stabilization energies.环状π电子离域的能量方面：芳香稳定化能估算方法的评估
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