Browse
Submit Data
Databases
API
Help

Dataset Information

23 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Charge Transfer Complexes of 1,3,6-Trinitro-9,10-phenanthrenequinone with Polycyclic Aromatic Compounds

ABSTRACT: Understanding the interactions of organic donor and acceptor molecules in binary associates is crucial for design and control of their functions. Herein, we carried out a theoretical study on the properties of charge transfer complexes of 1,3,6-trinitro-9,10-phenanthrenequinone (PQ) with 23 aromatic π-electron donors. Density functional theory (DFT) was employed to obtain geometries, frontier orbital energy levels and amounts of charge transfer in the ground and first excited states. For the most effective donors, namely, dibenzotetrathiafulvalene, pentacene, tetrathiafulvalene, 5,10-dimethylphenazine, and tetramethyl-p-phenylenediamine, the amount of charge transfer in the ground state was shown to be 0.134−0.240 e−. Further, a novel charge transfer complex of PQ with anthracene was isolated in crystalline form and its molecular and crystal structure elucidated by single-crystal synchrotron X-ray diffraction.

SUBMITTER: Linko R

PROVIDER: S-EPMC8588456 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Charge Transfer Complexes of New Sulfur- and Selenium-Rich Aromatic Donors.

Project description:Two new sulfur- and selenium-rich pentacyclic aromatic compounds were prepared by short chemical syntheses. The two donors readily formed charge transfer (CT) complexes upon reaction with antimony pentachloride or tris(4-bromophenyl)ammoniumyl hexachloroantimonate. The X-ray structures of the heterocyclic donors and their CT complexes were determined. The donors flattened considerably upon CT complex formation.

| S-EPMC9281308 | biostudies-literature

METABOLISM OF POLYCYCLIC COMPOUNDS. THE METABOLISM OF 9,10-EPOXY-9,10-DIHYDROPHENANTHRENE IN RATS.

Project description:1. 9,10-Epoxy-9,10-dihydrophenanthrene is converted by rats into trans-9,10-dihydro-9,10-dihydroxyphenanthrene and its conjugates and into N-acetyl-S-(9,10-dihydro-9-hydroxy-10-phenanthryl)-l- cysteine. Small amounts of 9-phenanthryl sulphate and glucosiduronate are also formed, together with 9-hydroxy-10-phenanthryl sulphate. 2. The epoxide readily rearranges to 9-hydroxyphenanthrene and reacts with water to give the dihydrodihydroxy compound and with N-acetylcysteine to give the mercapturic acid. One of the diastereoisomeric forms of the methyl ester of the mercapturic acid is identical with the ester of the mercapturic acid excreted by rats dosed with the epoxide or by rats and rabbits dosed with phenanthrene. 3. A rat-liver homogenate converts the epoxide into trans-9,10-dihydrodihydroxyphenanthrene and S-(9,10-dihydro-9-hydroxy-10-phenanthryl)glutathione. The latter compound was not formed when boiled rat-liver homogenate was used, but was formed chemically from the epoxide and glutathione under more vigorous conditions. 4. The results provide further indications that the metabolism of aromatic hydrocarbons involves the intermediary formation of epoxides.

| S-EPMC1206807 | biostudies-other

Ferrocenyl-Pyrenes, Ferrocenyl-9,10-Phenanthrenediones, and Ferrocenyl-9,10-Dimethoxyphenanthrenes: Charge-Transfer Studies and SWCNT Functionalization.

Project description:The synthesis of 1-Fc- (3), 1-Br-6-Fc- (5 a), 2-Br-7-Fc- (7 a), 1,6-Fc2 - (5 b), 2,7-Fc2 -pyrene (7 b), 3,6-Fc2 -9,10-phenanthrenedione (10), and 3,6-Fc2 -9,10-dimethoxyphenanthrene (12; Fc=Fe(η5 -C5 H4 )(η5 -C5 H5 )) is discussed. Of these compounds, 10 and 12 form 1D or 2D coordination polymers in the solid state. (Spectro)Electrochemical studies confirmed reversible Fc/Fc+ redox events between -130 and 160 mV. 1,6- and 2,7-Substitution in 5 a (E°'=-130 mV) and 7 a (E°'=50 mV) influences the redox potentials, whereas the ones of 5 b and 7 b (E°'=20 mV) are independent. Compounds 5 b, 7 b, 10, and 12 show single Fc oxidation processes with redox splittings between 70 and 100 mV. UV/Vis/NIR spectroelectrochemistry confirmed a weak electron transfer between FeII /FeIII in mixed-valent [5 b]+ and [12]+ . DFT calculations showed that 5 b non-covalently interacts with the single-walled carbon nanotube (SWCNT) sidewalls as proven by, for example, disentangling experiments. In addition, CV studies of the as-obtained dispersions confirmed exohedral attachment of 5 b at the SWCNTs.

| S-EPMC7064959 | biostudies-literature

Metabolism of a representative oxygenated polycyclic aromatic hydrocarbon (PAH) phenanthrene-9,10-quinone in human hepatoma (HepG2) cells.

Project description:Exposure to polycyclic aromatic hydrocarbons (PAHs) in the food chain is the major human health hazard associated with the Deepwater Horizon oil spill. Phenanthrene is a representative PAH present in crude oil, and it undergoes biological transformation, photooxidation, and chemical oxidation to produce its signature oxygenated derivative, phenanthrene-9,10-quinone. We report the downstream metabolic fate of phenanthrene-9,10-quinone in HepG2 cells. The structures of the metabolites were identified by HPLC-UV-fluorescence detection and LC-MS/MS. O-mono-Glucuronosyl-phenanthrene-9,10-catechol was identified, as reported previously. A novel bis-conjugate, O-mono-methyl-O-mono-sulfonated-phenanthrene-9,10-catechol, was discovered for the first time, and evidence for both of its precursor mono conjugates was obtained. The identities of these four metabolites were unequivocally validated by comparison to authentic enzymatically synthesized standards. Evidence was also obtained for a minor metabolic pathway of phenanthrene-9,10-quinone involving bis-hydroxylation followed by O-mono-sulfonation. The identification of 9,10-catechol conjugates supports metabolic detoxification of phenanthrene-9,10-quinone through interception of redox cycling by UGT, COMT, and SULT isozymes and indicates the possible use of phenanthrene-9,10-catechol conjugates as biomarkers of human exposure to oxygenated PAH.

| S-EPMC4028327 | biostudies-literature

Ring closing and opening reactions leading to aza-polycyclic aromatic compounds.

Project description:A series of functionalized aza-polycyclic aromatic compounds were prepared by a superacid-promoted ring closing and opening reaction cascade. A reaction mechanism is proposed, which involves reactive dicationic intermediates. A key step in the conversions involves ipso protonation of an aryl group and elimination of an alkyl phenyl group.

| S-EPMC3797622 | biostudies-literature

Polycyclic aromatic hydrocarbons degraders

Project description:Polycyclic aromatic hydrocarbons degraders Raw sequence reads

| PRJNA590550 | ENA

HepG2 treated with Polycyclic Aromatic Hydrocarbons (PAHs)

Project description:Assessing the potential carcinogenicity of human toxins represents an ongoing challenge. Chronic rodent bioassays predict human cancer risk with limited reliability, and are expensive and time-consuming. To identify alternative prediction methods, we evaluated a transcriptomics-based human in vitro model to classify carcinogens by their modes of action. The aim of this study was to determine the transcriptomic response and identify specific molecular signatures of polycyclic aromatic hydrocarbons (PAHs), which can be used as predictors of carcinogenicity of environmental toxins in human in vitro systems. We found that characteristic molecular signatures facilitate identification and prediction of carcinogens.

2012-04-18 | GSE37326 | GEO

Spectral, NBO, NLO, NCI, aromaticity and charge transfer analyses of anthracene-9,10-dicarboxaldehyde by DFT

Project description:Anthracene-9,10-dicarboxaldehyde (ADCA) is a polynuclear aromatic compound that has a planar structure with double bonds which are in conjugation. The molecule is subjected to theoretical investigation with DFT/B3LYP/6-311++G(d,p) basis set to find out the electronic structural properties and stability. Theoretical and experimental vibrational analyses are carried out. NBO studies predict that the molecule has high stability. NCI interaction studies reveal that Van der Waals force and steric effect are seen in the molecule. A shaded surface map with a projection of LOL analysis pointed out that electron depletion area is seen in this molecule. The tunnelling current is more in the boundary rings than the central ring. It is docked with the protein 4COF and the binding energy is found to be -6.6 kcal/mol. Electrons excitation analysis is performed and found that local excitation takes place for the lowest five excitations. The aromaticity of the molecule is also thoroughly investigated. Anthracene-9,10-dicarboxaldehyde, DFT, docking, NBO, non-covalent interaction, HOMA

| S-EPMC8605071 | biostudies-literature

Reactions of HDDA-Derived Benzynes with Perylenes: Rapid Construction of Polycyclic Aromatic Compounds.

Project description:Benzynes produced by the thermal cycloisomerization of tetrayne substrates [i.e., by the hexadehydro-Diels-Alder (HDDA) reaction] react with perylenes to produce novel naphthoperylene derivatives. Cyclic voltammetry and absorption and emission properties of these compounds are described. DFT studies shed additional light on the dearomatization that accompanies the reaction as well as some of the spectroscopic behavior.

| S-EPMC5107110 | biostudies-literature

Anomalies in the asymmetric transfer hydrogenation of several polycyclic meso compounds.

Project description:Over the course of developing a multigram scale preparation of epoxy quinol 1 via asymmetric transfer hydrogenation (ATH) using the Noyori Ru(arene)(S,S-TsDPEN) catalysts, we observed several unexpected phenomena, including (i) chemoselective alkene vs ketone reduction of an enedione, (ii) a significant arene ligand effect (p-cymene vs. mesitylene) on the reaction pathway, and (iii) solvent-based reversal of the sense of enantioinduction.

| S-EPMC3374411 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data