Electron affinities of benzo-, naphtho-, and anthraquinones determined from gas-phase equilibria measurements

Heinis, Thomas; Chowdhury, Swapan K.; Scott, Susannah L.; Kebarle, P.

doi:10.1021/ja00210a015

Cited by 107 publications

(79 citation statements)

References 1 publication

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“…236 Among various methods used the B3LYP/6-311G(3d,p) method yielding electron affinities within experimental error and within an average absolute magnitude of 0.05 eV of experimentally measured electron affinities. [237][238][239][240] Very recently the characterization of semiquinones and quinones formed as intermediates in the oxidation of flavonoid epicatechin has been studied by means of computational chemistry. 241 The antifungal and antioxidant activities of flavonoids depend on the stability of these semiquinones and quinones.…”

Section: Computational Investigations On 14-benzoquinonesmentioning

confidence: 99%

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

165

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As 1,4-benzoquinonas são encontradas em toda a natureza, podendo ser sintetizadas por diversas estratégias. Esta revisão apresenta os desenvolvimentos recentes das metodologias de síntese, das reações de ciclo adição, da química computacional e dos estudos de pulso radiolítico. Destaca ainda a sua significância química e biológica e de seus compostos derivados.1,4-Benzoquinones are ubiquitous in nature and can be synthesized by diverse strategies. Recent developments on their synthetic methodologies, cycloaddition reactions, computational chemistry and pulse radiolytic studies are reported in this review. Their chemical and biological significance as well as their derivates' are also covered.

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Section: Computational Investigations On 14-benzoquinonesmentioning

confidence: 99%

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

165

View full text Add to dashboard Cite

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“…Although, as stated in [5], the concept of Ôliquid phase photoionization potential is necessarily ambiguousÕ, inspection of the literature shows that from the experimental determination of I S it is possible to evaluate the oxidation potential of the ketones according to [19] where E RE ¼ 4:71 eV is the potential of the standard reference calomel electrode [19,20] and V 0 stands for the minimum energy of a Ôquasi-freeÕ electron in solvent relative to an electron in vacuum [19]. V 0 in acetonitrile was given as )0.14 eV [21].…”

Section: Threshold Excitation Wavelength K Thrmentioning

confidence: 99%

Tuning the ion formation processes from triplet–triplet annihilation to triplet-mediated photoionization

Jacques¹,

Allonas²,

Sarbach

et al. 2003

Chemical Physics Letters

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Free ion formation in acetonitrile is examined through transient photoconductivity for a set of ketones excited at different wavelengths. According to the photophysical parameters of the ketones and the incident photon energy, two mechanisms can be operative: triplet-triplet annihilation (bimolecular process) and/or photoionization (monomolecular biphotonic process). By using a tunable laser, excited state mediated photoionization was studied. From the threshold energy (E thr ) required for this process to occur, ionization potentials in solution (I S ) were deduced and compared to the corresponding values in gas phase (I G ). A simple energetic model enables the determination of the oxidation potential (E ox ) of the ketones that are compared to the corresponding values obtained through electrochemical measurements.

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“…For gas-phase systems, the majority of the reported studies is concerned with the determination of * Corresponding author. electron affinities [3][4][5][6][7][8][9] and the kinetics of electron transfer reactions involving stable radical anions or anions [3,10,11]. Only a limited number of studies have been concerned with the possible occurrence of electron transfer to haloalkanes in the gas phase [12][13][14][15][16][17][18] notwithstanding that special attention has been paid to the interplay between dissociative electron transfer and SN 2 substitution in reactions with 0168-1176/95/$09.50 © 1995 Elsevier Science B.V. All rights reserved SSDI 0168-1176(94)04127-X these compounds in the condensed phase [1,19].…”

Section: Introductionmentioning

confidence: 99%

Formation, stability and structure of radical anions of chloroform, tetrachloromethane and fluorotrichloromethane in the gas phase

Staneke

Groothuis

Ingemann

et al. 1995

International Journal of Mass Spectrometry and Ion Processes

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UvA-DARE is a service provided by the library of the University of Amsterdam (http://dare.uva.nl) UvA-DARE (Digital Academic Repository)Formation, stability and structure of radical anions of chloroform, tetrachloromethane and fluorotrichloromethane in the gas phase Staneke, P.O.; Groothuis, G.; Ingemann Jorgensen, S.; Nibbering, N.M.M. Disclaimer/Complaints regulationsIf you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the material inaccessible and/or remove it from the website. Please Ask the Library: http://uba.uva.nl/en/contact, or a letter to: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. You will be contacted as soon as possible. AbstractThe gas-phase reactions of the CH2S'-radical anion with chloroform, tetrachloromethane, and fluorotrichloromethane (CXC13; X = H, D, C1 and F) have been studied using Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometry. The primary reactions lead to minor amounts of the molecular radical anions of the halomethanes in addition to CHzSC1-and CI-, which are formed as the major product ions. The initial step is suggested to be electron transfer with formation of a [CHzS q-CXCI;-] ion/molecule complex, which may dissociate to the radical anion of the halomethane or react further to yield a [CH2S + C1-+ CXC1½-] complex prior to the generation of the C1-or CH2SC1-ions. The radical anions of CHC13 and CC14 react with the parent compounds to yield CHC14 and CCI;-ions, respectively, whereas CFClj transfer a C1 ion only to the CHsSH molecules also present in the FT-ICR cell. On the basis of the facile occurrence of CI-transfer, the CXCIs-ions are proposed to exist in a structure which can be described as a chloride ion weakly bonded to a CXCI2 radical. The formation of the CXCIs-ions in the reaction with the CHzS'-radical anion places a lower limit of 45kJmo1-1 for the electron affinities of the CXC13 molecules. The occurrence of CI-transfer from the CHCI~ ion to the parent compound leads to an indicated upper limit of 75 kJmo1-1 for the electron affinity of chloroform. Similarly, the occurrence of C1-transfer from the CC1U ion to the parent compound is used to derive an upper limit of 110 kJ mol 1 for the electron affinity of tetrachloromethane. These upper limits suggest that previously reported values overestimate the electron affinities of chloroform and tetrachloromethane.

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Electron affinities of benzo-, naphtho-, and anthraquinones determined from gas-phase equilibria measurements

Cited by 107 publications

References 1 publication

Recent advances in 1,4-benzoquinone chemistry

Recent advances in 1,4-benzoquinone chemistry

Tuning the ion formation processes from triplet–triplet annihilation to triplet-mediated photoionization

Formation, stability and structure of radical anions of chloroform, tetrachloromethane and fluorotrichloromethane in the gas phase

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