Aromaticity and Electron Density of Hypericin

被引：8

作者：

Szymanski, Sebastian ^{[1
]}

Majerz, Irena ^{[1
]}

机构：

[1] Wroclaw Med Univ, Fac Pharm, Borowska 211a, PL-50556 Wroclaw, Poland

来源：

JOURNAL OF NATURAL PRODUCTS | 2019年 / 82卷 / 08期

关键词：

ST-JOHNS-WORT; INDEPENDENT CHEMICAL-SHIFTS; PHOTODYNAMIC THERAPY; PERFORATUM; DELOCALIZATION; EXTRACTION; SIGMA; BIODISTRIBUTION; ANTIDEPRESSANT; DEPRESSION;

D O I：

10.1021/acs.jnatprod.8b00872

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

The influence of the substituents on the geometry of the central ring system of hypericin has been analyzed. Substitution that causes flattening of the hypericin central rings is connected with introducing the aromatic character of the empty rings. All the hypericin rings have an aromatic character illustrated by the Harmonic Oscillator Measure of Aromaticity (HOMA), Nucleus Independent Chemical Shift (NICS), Fluctuation Index (FLU), and Ellipticity Index (EL) indices. Quantum Theory of Atoms in Molecules (QTAIM) and Natural Bond Orbital (NBO) analyses performed on 7,14-dihydrophenanthro[1,10,9,8-opqra]perylene, its substituted analogues, and hypericin show an influence of this substitution on electron density of the central rings.

引用

页码：2106 / 2115

页数：10

共 50 条

[31] Aromaticity criteria based on electron delocalisation measures
Poater, Jordi
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[32] MAGNETIC-SUSCEPTIBILITY, ELECTRON DELOCALIZATION AND AROMATICITY
SCHMALZ, TG
GIERKE, TD
BEAK, P
FLYGARE, WH
TETRAHEDRON LETTERS, 1974, (33) : 2885 - 2888
[33] Electron-Deficiency Aromaticity in Silicon Nanoclusters
Vach, Holger
JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2012, 8 (06) : 2088 - 2094
[34] Assessment of the nature of interactions of cations with cycloheptatriene derivatives using change in the aromaticity: Comparison with electron density and NBO results
Valadbeigi, Younes
Gal, Jean-Francois
MOLECULAR PHYSICS, 2020, 118 (08)
[35] The Laplacian of Electron Density versus NICSzz Scan: Measuring Magnetic Aromaticity among Molecules with Different Atom Types
Foroutan-Nejad, Cina
Badri, Zahra
Shahbazian, Shant
Rashidi-Ranjbar, Parviz
JOURNAL OF PHYSICAL CHEMISTRY A, 2011, 115 (45): : 12708 - 12714
[36] Phosphole aromaticity enhancement by electron pumping through Schleyer hyperconjugative aromaticity: A comprehensive DFT study
Solgi, Leila
Mirjafary, Zohreh
Mokhtari, Javad
Saeidian, Hamid
CHEMICAL PHYSICS LETTERS, 2023, 821
[37] Benzenoid hydrocarbon aromaticity in terms of charge density descriptors
Howard, ST
Krygowski, TM
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1997, 75 (09): : 1174 - 1181
[38] Benzenoid hydrocarbon aromaticity in terms of charge density descriptors
Howard, S.T.
Krygowski, T.M.
Canadian Journal of Chemistry, 1997, 75 (09): : 1174 - 1181
[39] Theoretical basis for the correlation between energetic, magnetic, and electron density criteria of aromaticity: definition of molecular circuit electric conductance
Mandado, Marcos
THEORETICAL CHEMISTRY ACCOUNTS, 2010, 126 (5-6) : 339 - 349
[40] Theoretical basis for the correlation between energetic, magnetic, and electron density criteria of aromaticity: definition of molecular circuit electric conductance
Marcos Mandado
Theoretical Chemistry Accounts, 2010, 126 : 339 - 349

← 1 2 3 4 5 →