Synthesis and pesticidal activity of phenazines II.—Alkyl, alkoxy, alkylthio and alkylsulphonyl phenazines

Cross, B.; Dunn, C. L.; Payne, David H.; Tipton, J. D.

doi:10.1002/jsfa.2740200605

Cited by 11 publications

(5 citation statements)

References 2 publications

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“…Bis(μ‐hydroxo) species are commonly observed as decay products and often resulted from intramolecular hydroxylation of C−H bonds in α‐ or β‐position of N‐donor groups . Interestingly, [ H1 ] 2+ is the first example of a trinuclear μ‐alkoxo‐μ‐hydroxo copper(II) complex cation.…”

Section: Methodsmentioning

confidence: 99%

Exceptional Substrate Diversity in Oxygenation Reactions Catalyzed by a Bis(μ‐oxo) Copper Complex

Paul

Teubner

Grimm‐Lebsanft

et al. 2020

Chemistry A European J

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The enzyme tyrosinase contains a reactive side‐on peroxo dicopper(II) center as catalytically active species in C−H oxygenation reactions. The tyrosinase activity of the isomeric bis(μ‐oxo) dicopper(III) form has been discussed controversially. The synthesis of bis(μ‐oxo) dicopper(III) species [Cu2(μ‐O)2(L1)2](X)2 ([O1](X)2, X=PF6−, BF4−, OTf−, ClO4−), stabilized by the new hybrid guanidine ligand 2‐{2‐((dimethylamino)methyl)phenyl}‐1,1,3,3‐tetramethylguanidine (L1), and its characterization by UV/Vis, Raman, and XAS spectroscopy, as well as cryo‐UHR‐ESI mass spectrometry, is described. We highlight selective oxygenation of a plethora of phenolic substrates mediated by [O1](PF6)2, which results in mono‐ and bicyclic quinones and provides an attractive strategy for designing new phenazines. The selectivity is predicted by using the Fukui function, which is hereby introduced into tyrosinase model chemistry. Our bioinspired catalysis harnesses molecular dioxygen for organic transformations and achieves a substrate diversity reaching far beyond the scope of the enzyme.

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Section: Methodsmentioning

confidence: 99%

Exceptional Substrate Diversity in Oxygenation Reactions Catalyzed by a Bis(μ‐oxo) Copper Complex

Paul

Teubner

Grimm‐Lebsanft

et al. 2020

Chemistry A European J

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“…In this work, S θ can be directly obtained from the output files of Gaussian programs and presented in Table 3. Using multiple linear regression method of the SPSS 12.0 for windows program, the relation between N PCS and S θ can be seen in (6). The squared regression coefficient R 2 is 1000 and standard deviation SD is 0.05.…”

Section: Relation Of the Numbers And Positions Of Chlorine Substitutementioning

confidence: 99%

“…Natural and synthetic phenazines have attracted considerable attention because of their interesting biological activities [3], that is, antibiotic and anticancer agents [4,5]. Halosubstituted phenazines are useful as herbicides [6]. Because of there increasing dosage of chlorophenzines in recent years, their concentrations in the environment have also increased.…”

Section: Introductionmentioning

confidence: 99%

DFT Calculation on 76 Polychlorophenazines: Their Thermodynamic Function and Implication of Cl Substituted Position

Liu

Wang

et al. 2008

International Journal of Chemical Engineering

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Recommended by Z. ZhangThermodynamic functions, including enthalpy (H θ ) and entropy (S θ ) for 76 polychlorophenazines (PCPZs) in the gas state at 298.15 K and 101.325 kPa, have been calculated using the B3LYP/6-31G * level with Gaussian 03 program, and considered on solvation affects. Total free energy in water (G w ) was calculated with the same program. Based on these data, the isodesmic reactions were designed to calculate the standard formation heat (Δ f H θ ) and standard free energy of formation in water (Δ f G θ w ). The dependences of these thermodynamic parameters on the numbers and positions of chlorine substitution (N PCS ) were discussed. It is suggested that S θ , Δ f H θ , and Δ f G θ w of PCPZs varied greatly with N PCS . Moreover, the values of molar heat capacity at constant pressure (C p,m ) from 200 to 1800 K for PCPZ congeners were calculated using a statistical thermodynamics calculation program based on Gaussian output files, and the temperature-dependence relation of C p,m was obtained using the least-squares method. In addition, according to the relative magnitude of their Δ f G θ w , the relative stability order of PCPZ congeners was theoretically proposed.

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“…Mostly oligocenes are p–type materials which can be converted to n–type by introducing N‐atom in structural core of molecule as suggested by Winkler and Houk or by introducing electron withdrawing groups such as −F, −CN, −Cl, −NO 2, −COOH, etc . Pyrazino–Phenazine are important class of ‘N’ atom containing heterocyclic compounds widely demonstrated for biological properties such as antibacterial, antifungicidal, antitumor, antibiotic, antihypoxic, antileprosy, anthelminitic activity as well as it's halo substituted derivatives are useful as herbicides and able to retard metalloenzymes …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Opto‐electrochemical and Theoretical Investigation of Pyrazino[2, 3‐b]phenazine Amines for Organic Electronics

2018

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A series of five novel donor–acceptor molecules based on tetraazatetracene skeleton containing electron deficient pyrazino[2, 3‐b]phenazine core as acceptor and electron rich triarylamines as donor moiety have been synthesized by Buchwald−Hartwig coupling amination reaction and fully characterized. The synthesized molecules were studied for their optoelectronic properties. Absorption spectra of all the compounds showed intramolecular charge transfer (ICT) transitions in the range of 430−502 nm. All compounds emit in green−red region with emission maxima in the range of 491−639 nm on excitation at their respective ICT absorption maxima. The HOMO and LUMO energy level were found in the range of –5.40 to –5.66 eV and –3.69 to –3.84 eV respectively as calculated by cyclic voltammetry (CV). Theoretical studies were also carried out by using TD−DFT calculations. On the basis of HOMO and LUMO energy level, synthesized compounds could act as ambipolar materials in organic electronics.

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Synthesis and pesticidal activity of phenazines II.—Alkyl, alkoxy, alkylthio and alkylsulphonyl phenazines

Cited by 11 publications

References 2 publications

Exceptional Substrate Diversity in Oxygenation Reactions Catalyzed by a Bis(μ‐oxo) Copper Complex

Exceptional Substrate Diversity in Oxygenation Reactions Catalyzed by a Bis(μ‐oxo) Copper Complex

DFT Calculation on 76 Polychlorophenazines: Their Thermodynamic Function and Implication of Cl Substituted Position

Synthesis, Opto‐electrochemical and Theoretical Investigation of Pyrazino[2, 3‐b]phenazine Amines for Organic Electronics

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