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New modes of action of desferrioxamine: scavenging of semiquinone radical and stimulation of hydrolysis of tetrachlorohydroquinone.

Desferrioxamine (DFO) is a common drug used in the treatment of iron overload. In addition to its iron-chelation, other properties have been identified. Alas, DFO has demonstrable effects which cannot be explained by its classically established properties; i.e., DFO protects against DNA single strand breaks induced by tetrachlorohydroquinone (TCHQ), while other iron chelators such as DTPA (diethylenetriaminepentaacetic acid) do not. The autooxidation process of TCHQ yielding the tetrachlorosemiquinone radical (TCSQ.) intermediate, was studied here in the presence of chelators. DFO led to a marked reduction in both concentration and life span of TCSQ. via formation of DFO-nitroxide radical (DFO.). In contrast, DTPA had no detectable effect on TCHQ autooxidation. Present studies indicate that the protective effects of DFO on TCHQ-induced DNA damage were not due to the binding of iron, but rather to scavenging of the reactive TCSQ. and the formation of the less reactive DFO.. An additional mode of action of DFO was identified, via stimulation of the hydrolysis (dechlorination) of tetrachloro-1,4-benzoquinone (chloranil), which is the oxidation product of TCHQ, to form 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone (chloranilic acid). The results of this study demonstrate two new modes of action for DFO: the scavenging of deleterious semiquinone radical, and the stimulation of the hydrolysis of halogenated substituents on the quinone structure. Both modes might prove highly relevant to the biological activities of DFO.

Benzoquinones↗

Association of quinone-induced platelet anti-aggregation with cytotoxicity.

Various anti-platelet drugs, including quinones, are being investigated as potential treatments for cardiovascular disease because of their ability to prevent excessive platelet aggregation. In the present investigation 3 naphthoquinones (2,3-dimethoxy-1,4-naphthoquinone [DMNQ], menadione, and 1,4-naphthoquinone [4-NQ]) were compared for their abilities to inhibit platelet aggregation, deplete glutathione (GSH) and protein thiols, and cause cytotoxicity. Platelet-rich plasma, isolated from Sprague-Dawley rats, was used for all experiments. The relative potency of the 3 quinones to inhibit platelet aggregation, deplete intracellular GSH and protein thiols, and cause cytotoxicity was 1,4-NQ > menadione >> DMNQ. Experiments using 2 thiol-modifying agents, dithiothreitol (DTT) and 1-chloro-2,4-dintrobenzene (CDNB), confirmed the key roles for GSH in quinone-induced platelet anti-aggregation and for protein thiols in quinone-induced cytotoxicity. Furthermore, the anti-aggregative effects of a group of 12 additional quinone derivatives were positively correlated with their ability to cause platelet cytotoxicity. Quinones that had a weak anti-aggregative effect did not induce cytotoxicity (measured as LDH leakage), whereas quinones that had a potent anti-aggregative effect resulted in significant LDH leakage (84-96%). In one instance, however, p-chloranil demonstrated a potent anti-aggregative effect, but did not induce significant LDH leakage. This can be explained by the inability of p-chloranil to deplete protein thiols, even though intracellular GSH levels decreased rapidly. These results suggest that quinones that deplete GSH in platelets demonstrate a marked anti-aggregative effect. If this anti-aggregative effect is subsequently followed by depletion of protein thiols, cytotoxicity results.

Animals↗

Direct spectrofluorophotometric determination of porphyrin in diluted urine.

Direct dilution of freshly passed urine with 19 to 99 volumes of an acid-alcohol solution of chloranil (2, 3, 5, 6-tetrachloro-1, 4-benzoquinone) results in rapid and apparently quantitative conversion of porphyrinogen to fluorescing porphyrin. Dilution must be sufficient to yield an essentially colorless solution. Under these conditions, excitation of fluorescence by 401--405 nm light and fluorescence analysis at 652 nm results in almost complete elimination of quenching and of non-specific fluorescence under the conditions described. Fluorescence intensity is relatively stable for up to several weeks. Alternatively, urine is added to NaHCO3 to permit quantitative conversion of porphyrinogen to porphyrin in 1 to 2 days, and assayed similarly following dilution with the same acid-alcohol diluent (with or without chloranil) or with dilute HCl solution alone. Quantitative results are shown to agree well with those obtained following purification by other, more tedious, procedures. The method has been tested successfully with urines from humans, cows, and rats.

Bicarbonates↗

Use of pi-acceptors for spectrophotometric determination of dicyclomine hydrochloride.

Simple, rapid, accurate, and sensitive spectrophotometric methods are described for the determination of dicyclomine hydrochloride. The methods are based on the reaction of this drug as an n-electron donor with 2,3-dichloro-5,6-dicyano-p-benzoqunione (DDQ), p-chloranilic acid (p-CA), and chloranil (CL) as pi-acceptors to give highly colored complex species. The colored products are measured spectrophotometrically at 456, 530, and 650 nm for DDQ, p-CA, and CL, respectively. Optimization of the different experimental conditions were studied. Beer's law was obeyed in concentration ranges of 20-100, 50-250, and 80-600 microg/mL for DDQ, pCA, and CL, respectively. Colored complexes are produced in organic solvents and are stable for at least 1 h. The methods were applied to Spasmorest antispasmotic tablets and ampoules with good accuracy and precision.

Benzoquinones↗

Development and validation of spectrophotometric methods for determination of fluoxetine, sertraline, and paroxetine in pharmaceutical dosage forms.

Three simple and sensitive spectrophotometric methods were developed and validated for determination of the hydrochloride salts of fluoxetine, sertraline, and paroxetine in their pharmaceutical dosage forms. These methods were based on the reaction of the N-alkylvinylamine formed from the interaction of the free secondary amino group in the investigated drugs and acetaldehyde with each of 3 haloquinones, i.e., chloranil, bromanil, and 2,3-dichloronaphthoquinone, to give colored vinylamino-substituted quinones. The colored products obtained with chloranil, bromanil, and 2,3-dichloronaphthoquinone exhibit absorption maxima at 665, 655, and 580 nm, respectively. The factors affecting the reactions were studied and optimized. Under the optimum reaction conditions, linear relationships with good correlation coefficients (0.9986-0.9999) were found between the absorbances and the concentrations of the investigated drugs in the range of 4-120 microg/mL. The limits of detection for the assays ranged from 1.19 to 2.98 microg/mL. The precision values of the methods were satisfactory; the relative standard deviations were 0.56-1.24%. The proposed methods were successfully applied to the determination of the 3 drugs in pure and pharmaceutical dosage forms with good accuracy; the recoveries ranged from 99.1 to 101.3% with standard deviations of 1.15-1.92%. The results compared favorably with those of reported methods.

Acetaldehyde↗

Evaluation of the effect of terpenoid quinones on Trichophyton mentagrophytes by solution and vapor contact.

The antimicrobial activity against two bacterial strains and three fungi of five terpenoid quinones, three related quinones, and a quinone-containing essential oil was investigated by broth dilution and by agar vapor and box vapor assays. All the quinones, except for coenzyme Q10, exhibited their highest activity against Trichophyton mentagrophytes. Thymoquinone showed the most potent activity, not only by solution contact but also by vapor contact, with menadione the next most potent. Alizarin showed high activity only by solution contact. The antibacterial activity was related to the orthoquinone structure (1,2-chloranil and 1,2-naphthoquinone) and the antifungal activity was related to the paraquinone structure (chloranil, ubiquinone 0, thymoquinone, and menadione).

Anthraquinones↗

Automated determination of organic sulfur compounds. I. Spectrophotometric measurement of inorganic sulfate by low-pressure exchange chromatography.

A method for determination of inorganic sulfate is described which represents the terminal step of an automated assay of organic sulfur compounds in biological fluids. Nanomole quantities of inorganic sulfate were applied to a barium chloranilate column. Corresponding amounts of chloranilate ion, released as a result of an exchange reaction, were then measured by uv absorption at 313 nm. The reproducibility and sensitivity of the method and a calibration curve are reported.

Ammonium Sulfate↗

Spectrophotometric determination of beta-adrenergic blocking agents in pharmaceutical formulations.

Simple, rapid and sensitive spectrophotometric procedures were developed for the analysis of atenolol, timolol maleate, propranolol hydrochloride, metoprolol tartarate, betaxolol hydrochloride, levobunolol hydrochloride and bisprolol fumarate in pure form as well as in their pharmaceutical formulations. The methods are based on the reaction of these drugs as n-electron donors with the sigma-acceptor iodine, and the pi-acceptors: 7,7,8,8-tetracyanoquinodimethane, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, tetracyanoethylene, 2,3,5,6-tetrabromo-1,4-benzoquinone (bromanil) and 2,3,5,6-tetrachloro-1,4-benzoquinone (chloranil). The obtained charge-transfer complexes were measured at 365 nm for iodine (in 1,2-dichloroethane), at 840, 420, and 470 nm for 7,7,8,8-tetracyan-oquinodimethane, tetracyanoethylene and 2,3-di-chloro-5,6-dicyano-1,4-benzoquinone (in acetonitrile), respectively, and at 450 and 440 nm for bromanil and chloranil (in ethanol), respectively. Due to the rapid development of colors at ambient temperature, the obtained results were used on thin-layer chromatograms for the detection of the investigated drugs. Beer's plots were obeyed in a general concentration range of 4-120 microg ml(-1) with correlation coefficients not less than 0.9991. The proposed procedures could be applied successfully to the determination of the investigated drugs in tablets and ophthalmic solutions with good recovery; percent ranged from 98.03+/-0.98 to 100.30+/-0.90. The association constants and standard free energy changes using Benesi-Hildebrand plots were studied.

Adrenergic beta-Antagonists↗

Vertical ionisation potentials of a number of crown ethers from charge transfer bands of their EDA complexes.

Vertical ionisation potentials (I(v)D) of a number of crown ethers, viz. dibenzo-30-crown-10 (Crown 1), benzo-15-crown-5 (Crown 2), dibenzo-24-crown-8 (Crown 3), dicyclohexano-24-crown-8 (Crown 4) and 4'-nitrobenzo-15-crown-5 (Crown 5) are being reported for the first time from a study of EDA interaction of these crown ethers with a number of electron acceptors like C60, C70, o-chloranil, p-chloranil, 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) and pyromellitic diimide (PMD). The study has been carried out in CCl4 medium by electronic absorption spectroscopy. Charge transfer (CT) absorption bands in the 360-900 nm range have been found in each case (excepting the 60 fullerene-Crown 4 system). The vertical ionisation potentials (I(v)D) of all the crown ethers thus determined show a good correlation with those calculated by the semiempirical AM1 method. Of the six acceptors under study the vertical electron affinity of PMD was not found in the literature. This has also been determined from an analysis of the present h(nu)(CT) data.

Ethers, Cyclic↗

Excited-state energy-transfer dynamics in self-assembled triads composed of two porphyrins and an intervening Bis(dipyrrinato)metal complex.

The synthesis and characterization of various triads composed of a linear array of two zinc porphyrins joined via an intervening bis(dipyrrinato)metal(II) complex are reported. The preparation exploits the facile complexation of dipyrrins with divalent metal ions to give bis(dipyrrinato)metal(II) complexes [abbreviated (dp)(2)M]. Copper(II) and palladium(II) chelates of dipyrrins (available by oxidation of dipyrromethanes) were prepared in 50-80% yield. A one-flask synthesis of bis(dipyrrinato)zinc(II) complexes was developed by oxidation of a dipyrromethane with DDQ or p-chloranil in the presence of Zn(OAc)(2).2H(2)O in THF ( approximately 80% yield). Three routes were developed for preparing porphyrin-dipyrrins: (1). Suzuki coupling of a boronate-substituted zinc porphyrin (ZnP) and bis[5-(4-iodophenyl)dipyrrinato]Pd(II) to give the (ZnP-dp)(2)Pd triad (50% yield), followed by selective demetalation of the (dp)(2)Pd unit by treatment with 1,4-dithiothreitol under neutral conditions (71% yield); (2). oxidation of a porphyrin-dipyrromethane with p-chloranil in the presence of Zn(OAc)(2).2H(2)O followed by chromatography on silica gel (71% yield); and (3). condensation of a dipyrrin-dipyrromethane and a dipyrromethane-dicarbinol under InCl(3) catalysis followed by oxidation with DDQ (10-16% yield). Four triads of form (ZnP-dp)(2)Zn were prepared in 83-97% yield by treatment of a porphyrin-dipyrrin with Zn(OAc)(2).2H(2)O at room temperature. Free base dipyrrins typically absorb at 430-440 nm, while the bis(dipyrrinato)metal complexes absorb at 460-490 nm. The fluorescence spectra/yields and excited-state lifetimes of the (ZnP-dp)(2)Zn triad in toluene show (1). efficient energy transfer from the bis(dipyrrinato)zinc(II) chromophore to the zinc porphyrins (98.5% yield), and (2). little or no quenching of the resulting excited zinc porphyrin relative to the isolated chromophore. Taken together, these results indicate that bis(dipyrrinato)zinc(II) complexes can serve as self-assembling linkers that further function as secondary light-collection elements in porphyrin-based light-harvesting arrays.

Journal Article↗

Rational Design of a Novel Intercalation System. Layer-Gap Control of Crystalline Coordination Polymers, {[Cu(CA)(H(2)O)(m)()](G)}(n)() (m = 2, G = 2,5-Dimethylpyrazine and Phenazine; m = 1, G = 1,2,3,4,6,7,8,9-Octahydrophenazine).

New copper(II) intercalation compounds, {[Cu(CA)(H(2)O)(2)](G)}(n)() (H(2)CA = chloranilic acid; G = 2,5-dimethylpyrazine (dmpyz) (1a and 1b) and phenazine (phz) (2)) have been synthesized and characterized. 1acrystallizes in the triclinic space group P&onemacr;, with a = 8.028(2) Å, b = 10.269(1) Å, c = 4.780(2) Å, alpha = 93.85(3) degrees, beta = 101.01(2) degrees, gamma = 90.04(3) degrees, and Z = 1. 1b crystallizes in the triclinic space group P&onemacr;, with a = 8.010(1) Å, b = 10.117(1) Å, c = 5.162(1) Å, alpha = 94.40(1) degrees, beta = 97.49(1) degrees, gamma = 112.64(1) degrees, and Z = 1. 2crystallizes in the triclinic space group P&onemacr;, with a = 8.071(1) Å, b = 11.266(1) Å, c = 4.991(1) Å, alpha = 97.80(1) degrees, beta = 99.58(1) degrees, gamma = 83.02(1) degrees, and Z = 1. For all the compounds, the crystal structures consist of one dimensional [Cu(CA)(H(2)O)(2)](m)() chains and uncoordinated guest molecules (G). Each copper atom for 1a, 1b, and 2 displays a six-coordinate geometry with the two bis-chelating CA(2)(-) anions and water molecules, providing an infinite, nearly coplanar linear chains running along the a-direction. Theses chains are linked by hydrogen bonds between the coordinated water and the oxygen atoms of CA(2)(-) on the adjacent chain, forming extended layers, which spread out along the ac-plane. The guest molecules are intercalated in between the {[Cu(CA)(H(2)O)(2)](k)()}(l)() layers, just like pillars, which are supported with N.H(2)O hydrogen bonding. The guest molecules are stacked each other with an interplanar distance of ca. 3.2 Å along the c-axis perpendicular to the [Cu(CA)(H(2)O)(2)](m)() chain. The EHMO band calculations of intercalated dmpyz and phz columns show an appreciable band dispersion of phz pi (b(2g) and b(3g)) and dmpyz pi (b(g)), indicative of the importance of planar pi structure for the formation of the intercalated structure. The distances of O-H---N (guest molecules) fall within the range 2.74-2.80 Å, insensitive to the guest, whereas the interlayer distances increase in the order 9.25 Å (1b), 10.24 Å (1a), and 11.03 Å (2). The degree in lengthening the distance correlates well with the size of a molecule, indicative of the stability of the 2-D sheet structure and the flexibility of the sheet packing. The magnetic susceptibilities were measured from 2 to 300 K and analyzed by a one-dimensional Heisenberg-exchange model to yield J = -1.83 cm(-)(1), g = 2.18 (1a), J = -0.39 cm(-)(1), g = 2.14 (1b), and J = -1.84 cm(-)(1), g = 2.18 (2). The absolute value of J is smaller than that value for [Cu(CA)](n)(), which has a planar ribbon structure suggesting that the magnetic orbital d(x)()()2(-)(y)()()2 is not parallel to the chloranilate plane. For comparison with phz another type of copper(II) coordination compound, {[Cu(CA)(H(2)O)](ohphz)}(n)() (ohphz = 1,2,3,4,6,7,8,9-octahydrophenazine (7)) has also been obtained. 7 crystallizes in the orthorhombic space group Cmcm with a = 7.601(2) Å, b = 13.884(2) Å, c = 17.676(4) Å, and Z = 4. Nonplanar ohphz molecules are in between [Cu(CA)(H(2)O)(2)](m)() chains with the N.H(2)O hydrogen bonding in a fashion parallel to the chain direction. The copper atom shows a five-coordinate square-pyramidal configuration with two CA and one water molecule, thus affording no hydrogen bonding links between chains, dissimilar to 1a, 1b, and 2. The magnetic susceptibilities yield J = -10.93 cm(-)(1) and g = 2.00, comparable to that of the four-coordinate [Cu(CA)](n)(). On this basis both hydrogen bonding and stack capability of a guest molecule is responsible for building the unique intercalated structure such as is seen in 1a, 1b, and 2.

Journal Article↗

Competitive consecutive electron transfer in determination of ionization potentials: ketene derivatives.

Kinetics of competitive consecutive electron transfer was used to determine ionization potentials of transient species. Kinetics of two-stage electron transfer reactions in aprotic solvent was studied using 355 nm laser flash photolysis. The concentrations of transients produced by the laser flash photolysis were monitored by their light absorption. Triplet-excited tetrachloro-p-benzo-quinone (p-chloranil) generated by a 355 nm laser flash oxidized diethyl ketene, diphenyl ketene, or phenyl ethyl ketene to form radical cations. The ketene radical cations, in turn, oxidized tertiary amine, forming ground state ketene and ammonium radical cation. The kinetics of the disappearance of ketene radical cations (and/or appearance of ammonium radical cations) due to consecutive, competitive electron transfer to ketene and p-chloranil radical cations was monitored. By monitoring kinetics in the presence of tertiary amines with different oxidation potentials, it was established that in acetonitrile the oxidation potential of diethyl ketene was 5.4 eV; for phenyl ethyl ketene, it was approximately 4.8 eV; and for diphenyl ketene, it was 4.6 eV. The results were in agreement with the oxidation potentials of ketenes computed using published data.

Journal Article↗

Alteration in cell permeability as a mechanism of action of certain quinone pesticides.

The permeability of the Chlorella pyrenoidosa membrane was studied by following the efflux of (14)C-intracellular material from cells which had been allowed to incorporate (14)CO(2) photosynthetically. It was observed that the efflux increased upon treatment with low concentrations (3-30 muM) of 2, 3-dichloro-1, 4-naphthoquinone (dichlone), 2-amino-3-chloro-1, 4-naphthoquinone (06K-quinone), and 2, 3, 5, 6-tetrachloro-1, 4-benzoquinone (chloranil). Dichlone caused a greater loss of intracellular material than chloranil or 06K-quinone. The rate of loss as well as the total loss of (14)C increased with an increase in the concentration of the quinones. In the dichlone-treated cells, the leakage was observed within 1 minute of the addition of the chemical and the effect on cell permeability was irreversible. Cells exposed to dichlone in the light or under anaerobic conditions released significantly greater amounts of (14)C-material than cells treated in the dark or under aerobic conditions. The aqueous ethanol-soluble fraction of the cell was found to be the source of the released material. The proportion of the ethanol-soluble (14)C that leaked out of the cell varied with the time of (14)C-assimilation prior to treatment with dichlone. In the dichlone-treated cells, practically all the (14)C-sucrose, alanine, glutamine, serine, and glycine leaked out, whereas glutamic, aspartic, succinic, and fumaric acids were lost only partially. Essentially no (14)C-lipids were lost from the cells during dichlone treatment.The extreme rapidity of the effect of dichlone on permeability and the low concentrations at which dichlone acted suggest that the cell membrane may be a primary site of action of dichlone, and that the metabolic changes observed in dichlone-treated Chlorella may be due to the changes in the cell membrane structure.

Journal Article↗

Spectrophotometric determination of rifampicin through chelate formation and charge transfer complexation in pharmaceutical preparation and biological fluids.

Two simple and accurate spectrophotometric methods for determination of Rifampicin (RIF) are described. The first method is based on charge transfer (CT) complex formation of the drug with three pi-electron acceptors either 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), 7,7,7,8-Tetracyanoquinodimethane (TCNQ) or 2,3,5,6-Tetrachloro-1,4-benzoquinone (p-chloranil) in acetonitrile. The method is followed spectrophotometrically by measuring the maximum absorbance at 584 nm, 761 nm (680 nm) or 560 nm for DDQ, TCNQ and p-chloranil, respectively. Under the optimized experimental conditions, the calibration curves showed a linear relationship over the concentration ranges of 5-140 microg/ml, 2-45 microg/ml (5-120 microg/ml) and 15-200 microg/ml, respectively. The second method is based on the reaction of RIF with iron(III) forming a water insoluble violet complex which is extracted into chloroform. The method determines RIF in concentration range of 10-240 microg/ml at 540 nm. The proposed methods applied to determination of RIF in capsule, human serum and urine samples with good accuracy and precision. The results were compared statistically with the official method and showed no significant different between the methods compared in terms of accuracy and precision.

Calibration↗

Detection of halofantrine, mefloquine and proguanil by charge--transfer complexation on thin layer plates.

A complexation phenomenon between certain antimalarials (as donors) and chloranilic acid (as an acceptor) has been studied using thin-layer-chromatography (TLC). The antimalarials were subjected to charge--transfer complexation using chloranilic acid as the pi-acceptor. This technique was used for the qualitative detection of the drugs. Drug-spotted TLC plates, when developed in suitable solvent systems and sprayed with the pi-acceptor gave a spontaneous purple colour. The Rr values of the three drugs were found to be constant and specific for each drug sample in a particular solvent system.

Antimalarials↗

[Spectrophotometric determination of azithromycin by charge transfer reaction].

The charge transfer interactions of Azithromycin and 7,7,8,8-tetracyanoquinodimethane (TCNQ) or chloranilic acid (CL) were investigated by spectrophotometry. The apparent molar absorptivity of TCNQ complex is 2.7 x 10(4) L x mol(-1) x cm(-1) at 743 nm, and 5.0 x 10(4) L x mol(-1) x cm(-1) at 842 nm; and that of CL complex is 2.4 x 10(3) L x mol(-1) x cm(-1). Beers law is obeyed in the concentration range of 0-30 mg x L(-1) for TCNQ method, and 5-225 mg x L(-1) for CL method. The relative standard deviations of the two methods are 1.0% and 1.4% (n = 6), respectively. The composition of complex of Azithromycin with 7,7,8,8-tetracyanoquinodimethane or chloranilic acid is 1 : 2. This proposed method has been applied to the determination of Azithromycin in tablets with satisfactory results.

Anti-Bacterial Agents↗

The effect of pressure on hydrogen transfer reactions with quinones.

The effect of pressure on the oxidation of hydroarenes 3-9 with 2,3-dichloro-5,6-dicyano-1,4-quinone (DDQ; 1 a) or o-chloranil (10), leading to the corresponding arenes, has been investigated. The activation volumes were determined from the pressure dependence of the rate constants of these reactions monitored by on-line UV/Vis spectroscopic measurements in an optical high-pressure cell (up to 3500 bar). The finding that they are highly negative and only moderately dependent on the solvent polarity (DeltaV( not equal ) = -13 to -25 in MTBE and -15 to -29 cm(3) mol(-1) in MeCN/AcOEt, 1:1) rules out the formation of ionic species in the rate-determining step and is good evidence for a hydrogen atom transfer mechanism leading to a pair of radicals in the rate-determining step, as was also suggested by kinetic measurements, studies of kinetic isotope effects, and spin-trapping experiments. The strong pressure dependence of the kinetic deuterium isotope effect for the reaction of 9,10-dihydroanthracene 5/5-9,9,10,10-D(4) with DDQ (1 a) can be attributed to a tunneling component in the hydrogen transfer. In the case of formal 1,3-dienes and enes possessing two vicinal C--H bonds, which have to be cleaved during the dehydrogenation, a pericyclic hydrogen transfer has to considered as one mechanistic alternative. The comparison of the kinetic deuterium isotope effects determined for the oxidation of tetralin 9/9-1,1,4,4-D(4)/9-2,2,3,3-D(4)/9-D(12) either with DDQ (1 a) or with thymoquinone 1 c indicates that the reaction with DDQ (1 a) proceeds in a stepwise manner through hydrogen atom transfer, analogously to the oxidations of 1,4-dihydroarenes, whereas the reaction with thymoquinone 1 c is concerted, following the course of a pericyclic hydrogen transfer. The difference in the mechanistic courses of these two reactions may be explained by the effect of the CN and Cl substituents in 1 a, which stabilize a radical intermediate better than the alkyl groups in 1 c. The mechanistic conclusions are substantiated by DFT calculations.

Benzoquinones↗

Calculations of multipulse sequence in NQR of spins 32.

The general formalism of the interaction representation with respect to an operator which is its own inverse is developed and applied to pure NQR of spins I = 32. Under the assumption of no relaxation and no dipolar coupling, it is shown that the calculation of the response to pure NQR multipulse sequences can be performed with the same concepts used in high field NMR, such as coherence pathways. All the tools and mathematical expressions to predict the time evolution of the signal created by a pure NQR multipulse sequence are presented explicitly. It takes into account the off-resonance irradiation as well as the angular dependence of the excitation and detection for every value of the electric field gradient asymmetry parameter. Particular attention is devoted to the powder average, which is performed via a probability function derived analytically for the first time, leading to a drastic reduction of simulation times. The theory is illustrated by the study of the optimization and excitation bandwidths of one- to three-pulse sequences and compared to experimental results on Chloranil. We show that the three-pulse "stimulated echo" sequence gives a more uniform excitation profile than the traditional two-pulse echo sequence for powder samples. Thus, the "stimulated echo" sequence could be useful to cover a large spectrum when the experiment duration, or the signal to noise ratio, are not critical parameters. Analytical expressions for the nutation spectra obtained by one or two-pulse sequences are also derived for the first time.

Chloranil↗