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Статті в журналах з теми "Hydride Transfer Chemistry"

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Автор: Grafiati

Опубліковано: 6 вересня 2023

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1

McSkimming, Alex, Jordan W. Taylor, and W. Hill Harman. "Assembly and Redox-Rich Hydride Chemistry of an Asymmetric Mo2S2 Platform." Molecules 25, no. 13 (July 7, 2020): 3090. http://dx.doi.org/10.3390/molecules25133090.

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Although molybdenum sulfide materials show promise as electrocatalysts for proton reduction, the hydrido species proposed as intermediates remain poorly characterized. We report herein the synthesis, reactions and spectroscopic properties of a molybdenum-hydride complex featuring an asymmetric Mo2S2 core. This molecule displays rich redox chemistry with electrochemical couples at E½ = −0.45, −0.78 and −1.99 V vs. Fc/Fc+. The corresponding hydrido-complexes for all three redox levels were isolated and characterized crystallographically. Through an analysis of solid-state bond metrics and DFT calculations, we show that the electron-transfer processes for the two more positive couples are centered predominantly on the pyridinediimine supporting ligand, whereas for the most negative couple electron-transfer is mostly Mo-localized.

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2

Fukuzumi, Shunichi, Toshiaki Kitano, Masashi Ishikawa, and Yoshiharu Matsuda. "Electron transfer chemistry of hydride and carbanion donors. Hydride and carbanion transfer via electron transfer." Chemical Physics 176, no. 2-3 (October 1993): 337–47. http://dx.doi.org/10.1016/0301-0104(93)80244-4.

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3

Chan, Bun, and Masanari Kimura. "High-level quantum chemistry exploration of reduction by group-13 hydrides: insights into the rational design of bio-mimic CO₂ reduction." Electronic Structure 4, no. 4 (November 7, 2022): 044001. http://dx.doi.org/10.1088/2516-1075/ac9bb3.

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Abstract In the present study, we have used computational quantum chemistry to explore the reduction of various types of substrates by group-13 hydrides. We use the high-level L-W1X method to obtain the energies for the constituent association and hydride transfer reactions. We find that the hydride transfer reactions are highly exothermic, while the preceding association reactions are less so. Thus, improving the thermodynamics of substrate association may improve the overall process. Among the various substrates, amine and imine show the strongest binding, while CO2 shows the weakest. Between the group-13 hydrides, alanes bind most strongly with the substrates, and they also have the most exothermic hydride transfer reactions. To facilitate CO2 binding, we have examined alanes with electron-withdrawing groups, and we indeed find CF3 groups to be effective. Drawing inspiration from the RuBisCO enzyme for CO2 fixation, we have further examined the activation of CO2 with two independent AlH(CF3)2 molecules, with the results showing an even more exothermic association. This observation may form the basis for designing an effective dialane reagent for CO2 reduction. We have also assessed a range of lower-cost computational methods for the calculation of systems in the present study. We find the DSD-PBEP86 double-hybrid DFT method to be the most suitable for the study of related medium-sized systems.

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4

Bohra, Anupama, Pradeep K. Sharma, and Kalyan K. Banerji. "Kinetics and Mechanism of the Oxidation of Aliphatic Aldehydes by Benzyltrimethylammonium Chlorobromate." Journal of Chemical Research 23, no. 5 (May 1999): 308–9. http://dx.doi.org/10.1177/174751989902300506.

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5

Zhao, Yin, Helmut W. Schmalle, Thomas Fox, Olivier Blacque, and Heinz Berke. "Hydride transfer reactivity of tetrakis(trimethylphosphine)(hydrido)(nitrosyl)molybdenum(0)." Dalton Trans., no. 1 (2006): 73–85. http://dx.doi.org/10.1039/b511797f.

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6

Wel, Hans van der, Nico M. M. Nibbering, and Margaret M. Kayser. "A gas phase study of the regioselective BH4− reduction of some 2-substituted maleic anhydrides." Canadian Journal of Chemistry 66, no. 10 (October 1, 1988): 2587–94. http://dx.doi.org/10.1139/v88-406.

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Анотація:

Gas phase ion/molecule reactions in a Fourier transform ion cyclotron resonance mass spectrometer have been carried out for reductions of isotopically labelled citraconic (methylmaleic), phenylmaleic, and ethoxymaleic anhydrides by BH4−. In citraconic anhydride the carbonyl group neighbouring the methyl substituent is reduced preferentially in agreement with the ab initio calculations, which show the higher LUMO coefficients at this site. Hydride ion transfer to the olefinic double bond occurs as well; however, in that case no preference for either of the carbon atoms is observed. In phenylmaleic anhydride strong indications are found for a theoretically unexpected hydride ion transfer to the phenyl ring. For ethoxymaleic anhydride experimental evidence is presented showing hydride ion transfer to the carbon atom carrying the ethoxy group, which is in agreement with the "best overlap" consideration predicting that this carbon atom bears the highest LUMO coefficient.Most of the hydride transfers from BH4− to the molecules studied seem, therefore, to take place under orbital control rather than under control of long-range ion-induced dipole interactions between reactants.

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7

Zaman, Khan M., Norio Nishimura, Shunzo Yamamoto, and Yoshimi Sueishi. "Hydride transfer reactions of Michler's hydride with different ?-accetors." Journal of Physical Organic Chemistry 7, no. 6 (June 1994): 309–15. http://dx.doi.org/10.1002/poc.610070607.

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8

FUKUZUMI, SHUNICHI, and SOUTA NOURA. "Cobalt(III) Porphyrin-catalysed Hydride Reduction of 10-Methylacridinium ion and Hydrometallation of Alkenes and Alkynes by Tributyltin Hydride." Journal of Porphyrins and Phthalocyanines 01, no. 03 (July 1997): 251–58. http://dx.doi.org/10.1002/(sici)1099-1409(199707)1:3<251::aid-jpp24>3.0.co;2-p.

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Анотація:

Cobalt(III) tetraphenylporphyrin catalyses a hydride transfer reaction from tributyltin hydride to 10-methylacridinium ion via the formation of hydridocobalt(III) tetraphenylporphyrin, which is the rate-determining step, followed by facile hydride transfer from the hydridocobalt(III) porphyrin to 10-methylacridinium ion in acetonitrile. Tributyltin hydride is also effective for the hydrometallation of alkenes and alkynes with cobalt(III) tetraphenylporphyrin to yield the corresponding organocobalt(III) porphyrins regioselectively. The hydrometallation is suggested to proceed via the hydride transfer from tributyltin hydride to cobalt(III) tetraphenylporphyrin to give the hydridocobalt(III) porphyrin, followed by the hydrogen transfer from hydridocobalt(III) porphyrin to alkenes and alkynes to yield the corresponding organocobalt(III) porphyrins. The regioselectivities are consistent with the stabilities of radicals generated by the hydrogen transfer from hydridocobalt(III) porphyrin to alkenes and alkynes. The rates of the electrophilic cleavage of cobalt-carbon bonds of organocobalt(III) porphyrins by trifluoroacetic acid in MeCN are also reported.

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9

Tassano, Erika, and Mélanie Hall. "Enzymatic self-sufficient hydride transfer processes." Chemical Society Reviews 48, no. 23 (2019): 5596–615. http://dx.doi.org/10.1039/c8cs00903a.

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Enzymatic self-sufficient hydride transfer processes. The hydride shuttle used in catalytic quantities is typically a nicotinamide cofactor (full: reduced; empty: oxidized). Ideally, no electron is lost to ‘the outside’ and no waste is produced.

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10

Casey, Charles P., and Jeffrey B. Johnson. "Kinetic isotope effect evidence for the concerted transfer of hydride and proton from hydroxycyclopentadienyl ruthenium hydride in solvents of different polarities and hydrogen bonding ability." Canadian Journal of Chemistry 83, no. 9 (September 1, 2005): 1339–46. http://dx.doi.org/10.1139/v05-140.

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The tolyl analogue of Shvo's hydroxycyclopentadienyl ruthenium hydride (4) efficiently transfers a hydride and proton to benzaldehyde or acetophenone to produce an alcohol. This reduction can be performed in toluene, methylene chloride, and THF. Reduction of benzaldehyde in toluene and methylene chloride occurs approximately 300 times faster than in THF at 0 °C. Reduction of acetophenone occurs between 75 and 150 times slower than benzaldehyde at 0 °C in each respective solvent. Despite the differences in rate, mechanistic studies have provided evidence for a similar concerted transfer of acidic and hydridic hydrogens in each solvent. Addition of water to THF led to further rate decrease coupled with an increase in the OH/D kinetic isotope effect and a decrease in the RuH/D kinetic isotope effect. Addition of excess alcohol to toluene or methylene chloride results in the significant retardation of the rate of reduction. The slower rate in THF and in the presence of alcohol is attributed to the stabilization of the ground state of ruthenium hydride 4 by hydrogen bonding and the additional energy required to break these bonds prior to carbonyl reduction.Key words: ruthenium hydrogenation catalysis, hydrogenation mechanism, kinetic isotope effects, ligandmetal bifunctional catalysis.

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11

Pankratov, Alexei, and Boris Drevko. "An approach to quantum chemical consideration of "hydride" transfer reaction." Journal of the Serbian Chemical Society 69, no. 6 (2004): 431–39. http://dx.doi.org/10.2298/jsc0406431p.

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Анотація:

An approach to the quantum chemical study of "hydride ion" transfer has been proposed, according to which the sequences of changes in ionization potentials, enthalpies and free energies of the affinities to the hydride ion, to the hydrogen atom and to the proton of substrates molecules and their derivatives (cations, radicals, anions), are compared with the experimentally substantiated series of "hydride" mobility. It has been established that the experimental series of "hydride" mobility for six chalcogenopyrans based on "semicyclic" 1,5-diketones is in conformity with the computed ionization potentials of themolecules, and with the affinity of the corresponding radicals to the hydrogen atom involved in the transfer. The direct splitting-out of the hydride ion and the primary deprotonation of the substrates followed by the withdrawal of two electrons was elucidated to be unlikely. Feasible are the mechanisms of "hydride" mobility, the first step of which consists of electron or hydrogen atom transfer from the chalcogenopyrans molecules.

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12

Brouwer, D. M., and A. A. Kiffen. "Hydride transfer reactions: IV. Intramolecular hydride shifts in protonated aldehydes." Recueil des Travaux Chimiques des Pays-Bas 92, no. 8 (September 2, 2010): 906–14. http://dx.doi.org/10.1002/recl.19730920812.

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13

Anne, Agnès, and Jacques Moiroux. "Thermodynamic characteristics of NADH/NAD+ analogues in acetonitrile: 2-methyl, 4-methyl and 2,4-dimethyl 1-benzyl-dihydronicotinamides and the corresponding pyridinium species." Canadian Journal of Chemistry 73, no. 4 (April 1, 1995): 531–38. http://dx.doi.org/10.1139/v95-068.

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Анотація:

Procedures were elaborated for the syntheses of the title compounds. The thermodynamic changes brought about by each methyl substitution were then determined quantitatively. In acetonitrile, the respective one-electron oxidation and one-electron reduction potentials of the NADH and NAD+ analogues were obtained by means of direct and indirect (using ferrocene mediators) cyclic voltammetry. The redox potentials of formal hydride transfers were deduced from the studies of equilibrated reactions occurring between the analogues. The pKa's of the cation radicals ensued. Keywords: NADH/NAD+ methylated analogues, one-electron transfers, hydride transfer, thermodynamics.

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14

Zhang, Fanjun, Jiong Jia, Shuli Dong, Wenguang Wang, and Chen-Ho Tung. "Hydride Transfer from Iron(II) Hydride Compounds to NAD(P)+ Analogues." Organometallics 35, no. 8 (April 5, 2016): 1151–59. http://dx.doi.org/10.1021/acs.organomet.6b00179.

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15

Silva, Rosalice Mendonça, and Marcetta Y. Darensbourg. "The Hydride Transfer Ability of a Neutral Hydride, CP2Nb(H)CO." Journal Of The Brazilian Chemical Society 3, no. 3 (1992): 55–60. http://dx.doi.org/10.5935/0103-5053.19920011.

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16

Formosinho, Sebasti�o J. "Theoretical studies of hydride transfer reactions." Journal of Physical Organic Chemistry 3, no. 5 (May 1990): 325–31. http://dx.doi.org/10.1002/poc.610030509.

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17

Belkova, N. V., E. I. Gutsul, E. S. Shubina, and L. M. Epstein. "Proton Transfer to Organometallic Hydrides via Unconventional Hydrogen Bonding: Problems and Perspectives." Zeitschrift für Physikalische Chemie 217, no. 12 (December 1, 2003): 1525–38. http://dx.doi.org/10.1524/zpch.217.12.1525.20482.

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AbstractThis review summarizes the spectral and theoretical results concerning different ways of proton transfer through hydrogen bonds (HB) to metal atoms (XH···M) and hydride ligands (XH···HM) leading to classical and nonclassical cationic hydrides. The spectral (NMR, IR, UV-Vis in the temperature range 190–290K) and theoretical studies of the structural and energetic characteristics of HB intermediates and proton transfer allow the representation of the experimental energy profiles. The problems concerning the influence of different factors on the processes and potential energy surfaces requiring active investigations in this new area are discussed

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18

Holewinski, Adam. "Hydride transfer gets a recharge." Nature Catalysis 6, no. 4 (April 26, 2023): 296–97. http://dx.doi.org/10.1038/s41929-023-00946-z.

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19

Cui, Xin, Wei Huang, and Lipeng Wu. "Zirconium-hydride-catalyzed transfer hydrogenation of quinolines and indoles with ammonia borane." Organic Chemistry Frontiers 8, no. 18 (2021): 5002–7. http://dx.doi.org/10.1039/d1qo00672j.

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20

Connelly Robinson, Samantha J., Christopher M. Zall, Deanna L. Miller, John C. Linehan, and Aaron M. Appel. "Solvent influence on the thermodynamics for hydride transfer from bis(diphosphine) complexes of nickel." Dalton Transactions 45, no. 24 (2016): 10017–23. http://dx.doi.org/10.1039/c6dt00309e.

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21

Hong, Baoyu, Majd Haddad, Frank Maley, Jan H. Jensen, and Amnon Kohen. "Hydride Transfer versus Hydrogen Radical Transfer in Thymidylate Synthase." Journal of the American Chemical Society 128, no. 17 (May 2006): 5636–37. http://dx.doi.org/10.1021/ja060196o.

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22

Pitman, C. L., O. N. L. Finster, and A. J. M. Miller. "Cyclopentadiene-mediated hydride transfer from rhodium complexes." Chemical Communications 52, no. 58 (2016): 9105–8. http://dx.doi.org/10.1039/c6cc00575f.

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Анотація:

Attempts to generate a proposed rhodium hydride catalytic intermediate instead resulted in isolation of (Cp*H)Rh(bpy)Cl (1), a pentamethylcyclopentadiene complex, formed by C–H bond-forming reductive elimination from the fleeting rhodium hydride.

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23

Ikeda, Glenn, and Ronald Kluger. "Deuterium labeling as a test of intramolecular hydride mechanisms in the fragmentation of 2-(1-hydroxybenzyl)-N1′-methylthiamin." Canadian Journal of Chemistry 83, no. 9 (September 1, 2005): 1277–80. http://dx.doi.org/10.1139/v05-146.

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2-(1-Hydroxybenzyl)-N1′-methylthiamin (1b) is a model for the addition intermediate in the thiamin catalyzed benzoin condensation. However, N-alkylation alters the reactivity of the compound: instead of undergoing base-catalyzed formation of benzaldehyde and N1′-methylthiamin, it rapidly forms trimethyl amino pyrimidine (2b) and phenylthiazole ketone (3). The base-catalyzed fragmentation process is faster than the analogous enzymic reaction (in benzoylformate decarboxylase) under the same conditions. One possible mechanism for the rapid fragmentation is an internal hydride transfer from α-C2 to the methylene bridge between the heterocycles. To test the hydride mechanism we prepared α-C2-deuterated 1b and conducted the fragmentation reaction in normal water. Spectroscopic analysis revealed that the trimethyl aminopyrimidine product does not contain any deuterium, ruling out a hydride transfer mechanism. This supports a mechanism for fragmentation that proceeds instead via a proton transfer from α-C2. Since protonation (and hence, deprotonation) of that site is part of the normal catalytic cycle of benzoylformate decarboxylase, the enzyme must divert the reaction from the lowest energy pathway since it would share a common intermediate with the fragmentation process.Key words: thiamin, fragmentation, benzoylformate decarboxylase, proton transfer, hydride shift.

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24

Coufourier, Sébastien, Daouda Ndiaye, Quentin Gaignard Gaillard, Léo Bettoni, Nicolas Joly, Mbaye Diagne Mbaye, Albert Poater, Sylvain Gaillard, and Jean-Luc Renaud. "Iron-catalyzed chemoselective hydride transfer reactions." Tetrahedron 90 (June 2021): 132187. http://dx.doi.org/10.1016/j.tet.2021.132187.

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25

Francisco Sánchez-Viesca and Reina Gómez. "On the chemistry of Beckurt’s test for physostigmine: A novel hydride transfer." Magna Scientia Advanced Research and Reviews 8, no. 2 (July 30, 2023): 022–25. http://dx.doi.org/10.30574/msarr.2023.8.2.0098.

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Beckurt treated physostigmine hydrochloride with dilute potassium permanganate solution and observed separation of manganese dioxide. Since at first sight there is no reaction site for this oxidation, it was interesting to clear up the reaction route of this test. Acid hydrolysis of this O-phenylcarbamate yielded the phenolic derivative of the three-ring indole alkaloid hydrochloride. Now are present at para-position an electrodotic group and a positive charged nitrogen atom. However, this nitrogen has an octet of electrons; thus, for reaction to occur a hydride ion must be displaced. This can happen in the presence of a hydride acceptor, that is, by reduction of permanganate ion. This chemical deportment has been postulated recently in a completely different reaction sequence. So, our proposal is a novel one. The mechanism of the following inorganic steps to the final product has not been advanced, and it is provided in this communication.

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26

Wu, Jinghua, and Zhiqiang Ma. "Metal-hydride hydrogen atom transfer (MHAT) reactions in natural product synthesis." Organic Chemistry Frontiers 8, no. 24 (2021): 7050–76. http://dx.doi.org/10.1039/d1qo01139a.

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27

Ai, Wenying, Rui Zhong, Xufang Liu, and Qiang Liu. "Hydride Transfer Reactions Catalyzed by Cobalt Complexes." Chemical Reviews 119, no. 4 (December 19, 2018): 2876–953. http://dx.doi.org/10.1021/acs.chemrev.8b00404.

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28

Osipova, Elena S., Sergey A. Kovalenko, Ekaterina S. Gulyaeva, Nikolay V. Kireev, Alexander A. Pavlov, Oleg A. Filippov, Anastasia A. Danshina, et al. "The Dichotomy of Mn–H Bond Cleavage and Kinetic Hydricity of Tricarbonyl Manganese Hydride Complexes." Molecules 28, no. 8 (April 11, 2023): 3368. http://dx.doi.org/10.3390/molecules28083368.

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Acid-base characteristics (acidity, pKa, and hydricity, ΔG°H− or kH−) of metal hydride complexes could be a helpful value for forecasting their activity in various catalytic reactions. Polarity of the M–H bond may change radically at the stage of formation of a non-covalent adduct with an acidic/basic partner. This stage is responsible for subsequent hydrogen ion (hydride or proton) transfer. Here, the reaction of tricarbonyl manganese hydrides mer,trans–[L2Mn(CO)3H] (1; L = P(OPh)3, 2; L = PPh3) and fac–[(L–L′)Mn(CO)3H] (3, L–L′ = Ph2PCH2PPh2 (dppm); 4, L–L′ = Ph2PCH2–NHC) with organic bases and Lewis acid (B(C6F5)3) was explored by spectroscopic (IR, NMR) methods to find the conditions for the Mn–H bond repolarization. Complex 1, bearing phosphite ligands, features acidic properties (pKa 21.3) but can serve also as a hydride donor (ΔG≠298K = 19.8 kcal/mol). Complex 3 with pronounced hydride character can be deprotonated with KHMDS at the CH2–bridge position in THF and at the Mn–H position in MeCN. The kinetic hydricity of manganese complexes 1–4 increases in the order mer,trans–[(P(OPh)3)2Mn(CO)3H] (1) < mer,trans–[(PPh3)2Mn(CO)3H] (2) ≈ fac–[(dppm)Mn(CO)3H] (3) < fac–[(Ph2PCH2NHC)Mn(CO)3H] (4), corresponding to the gain of the phosphorus ligand electron-donor properties.

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29

Peru, Filippo, Seyedhosein Payandeh, Torben R. Jensen, Georgia Charalambopoulou, and Theodore Steriotis. "Destabilization of the LiBH4–NaBH4 Eutectic Mixture through Pore Confinement for Hydrogen Storage." Inorganics 11, no. 3 (March 18, 2023): 128. http://dx.doi.org/10.3390/inorganics11030128.

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Анотація:

Both LiBH4 and NaBH4 are well known for having high hydrogen contents, but also high decomposition temperatures and slow hydrogen absorption–desorption kinetics, preventing their use for hydrogen storage applications. The low melting temperature (219 °C) of their eutectic mixture 0.71 LiBH4–0.29 NaBH4 allowed the synthesis of a new composite material through the melt infiltration of the hydrides into the ~5 nm diameter pores of a CMK-3 type carbon. A composite of 0.71 LiBH4–0.29 NaBH4 and non-porous graphitic carbon discs was also prepared by similar methods for comparison. Both composites showed improved kinetics and a partial reversibility of the dehydrogenation/rehydrogenation reactions. However, the best results were observed for the CMK-3 nanoconfined hydrides; a consistent uptake of about 3.5 wt.% H2 was recorded after five hydrogenation/dehydrogenation cycles for an otherwise non-reversible system. The improved hydrogen release kinetics are attributed to carbon–hydride surface interactions rather than nanoconfinement, while enhanced heat transfer due to the carbon support may also play a role. Likewise, the carbon–hydride contact proved beneficial in terms of reversibility, without, however, ruling out the potential positive effect of pore confinement.

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30

Kreevoy, Maurice M., and Ann T. Kotchevar. "Dynamics of hydride transfer between NAD+ analogs." Journal of the American Chemical Society 112, no. 9 (April 1990): 3579–83. http://dx.doi.org/10.1021/ja00165a049.

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31

Chen, Bao-Long, Sheng-Yi Yan, and Xiao-Qing Zhu. "A Mechanism Study of Redox Reactions of the Ruthenium-oxo-polypyridyl Complex." Molecules 28, no. 11 (May 28, 2023): 4401. http://dx.doi.org/10.3390/molecules28114401.

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Анотація:

Over the years, RuIV(bpy)2(py)(O)2+([RuIVO]2+) has garnered considerable interest owing to its extensive use as a polypyridine mono-oxygen complex. However, as the active-site Ru=O bond changes during the oxidation process, [RuIVO]2+ can be used to simulate the reactions of various high-priced metallic oxides. In order to elucidate the hydrogen element transfer process between the Ruthenium-oxo-polypyridyl complex and organic hydride donor, the current study reports on the synthesis of [RuIVO]2+, a polypyridine mono-oxygen complex, in addition to 1H and 3H (organic hydride compounds) and 1H derivative: 2. Through 1H-NMR analysis and thermodynamics- and kinetics-based assessments, we collected data on [RuIVO]2+ and two organic hydride donors and their corresponding intermediates and established a thermodynamic platform. It was confirmed that a one-step hydride transfer reaction between [RuIVO]2+ and these organic hydride donors occurs, and here, the advantages and nature of the new mechanism approach are revealed. Accordingly, these findings can considerably contribute to the better application of the compound in theoretical research and organic synthesis.

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32

Bunting, John W., and Mark A. Luscher. "Kinetics of hydride transfer between nitrogen heteroaromatic cations." Canadian Journal of Chemistry 66, no. 10 (October 1, 1988): 2524–31. http://dx.doi.org/10.1139/v88-396.

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The kinetics of the reduction of the 3-cyano-1-methylquinolinium, 4-cyano-2-methylisoquinolinium, and 2-methyl-5-nitro-isoquinolinium cations by 9,10-dihydro-10-methylacridine, and also the reduction of these same three cations as well as the 10-methylacridinium cation by 5,6-dihydro-5-methylphenanthridine, have been investigated in 20% acetonitrile – 80% water, ionic strength 1.0, 25 °C. The reactions of the 2-methyl-5-nitroisoquinolinium cation with both reductants, and also of the 4-cyano-2-methylisoquinolinium cation with 9,10-dihydro-10-methylacridine, display kinetic saturation effects in the pseudo-first-order rate constants as a function of heterocyclic cation concentration. These effects are consistent with the formation of 1:1 association complexes between hydride donor and acceptor prior to the rate-determining step of the reduction. The second-order rate constants for these reactions, and also those for analogous heterocyclic cation reductions by 1,4-dihydronicotinamides, show systematic variations as a function of the hydride donor and acceptor species.

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33

Chen, Juan, and Bo Liu. "Remote Chirality Transfer through Medium Cycle Formation/Intramolecular Hydride Transfer Cascade." Chinese Journal of Chemistry 38, no. 3 (February 18, 2020): 305–6. http://dx.doi.org/10.1002/cjoc.201900471.

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34

Weerasooriya, Ravindra B., Jonathan L. Gesiorski, Abdulaziz Alherz, Stefan Ilic, George N. Hargenrader, Charles B. Musgrave, and Ksenija D. Glusac. "Kinetics of Hydride Transfer from Catalytic Metal-Free Hydride Donors to CO2." Journal of Physical Chemistry Letters 12, no. 9 (March 2, 2021): 2306–11. http://dx.doi.org/10.1021/acs.jpclett.0c03662.

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35

Barrett, Seth M., Bethany M. Stratakes, Matthew B. Chambers, Daniel A. Kurtz, Catherine L. Pitman, Jillian L. Dempsey, and Alexander J. M. Miller. "Mechanistic basis for tuning iridium hydride photochemistry from H2 evolution to hydride transfer hydrodechlorination." Chemical Science 11, no. 25 (2020): 6442–49. http://dx.doi.org/10.1039/d0sc00422g.

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36

Bansal, Varsha, Pradeep K. Sharma, and Kalyan K. Banerji. "Kinetics and Mechanism of the Oxidation of Substituted Benzaldehydes by Oxo(salen)manganese(v) Complexes." Journal of Chemical Research 23, no. 8 (August 1999): 480–81. http://dx.doi.org/10.1177/174751989902300813.

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37

Zaman, Khan M., Shunzo Yamamoto, Norio Nishimura, Junichi Maruta, and Shunichi Fukuzumi. "Charge-Transfer Complexes Acting as Real Intermediates in Hydride Transfer from Michler's Hydride to 2,3-Dichloro-5,6-dicyano-p-benzoquinone via Electron Transfer." Journal of the American Chemical Society 116, no. 26 (December 1994): 12099–100. http://dx.doi.org/10.1021/ja00105a079.

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38

Ali, Qaim, Yongyong Chen, Ruixue Zhang, Zhewei Li, Yanhui Tang, Min Pu, and Ming Lei. "The Origin of Stereoselectivity in the Hydrogenation of Oximes Catalyzed by Iridium Complexes: A DFT Mechanistic Study." Molecules 27, no. 23 (November 30, 2022): 8349. http://dx.doi.org/10.3390/molecules27238349.

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Herein the reaction mechanism and the origin of stereoselectivity of asymmetric hydrogenation of oximes to hydroxylamines catalyzed by the cyclometalated iridium (III) complexes with chiral substituted single cyclopentadienyl ligands (Ir catalysts A1 and B1) under acidic condition were unveiled using DFT calculations. The catalytic cycle for this reaction consists of the dihydrogen activation step and the hydride transfer step. The calculated results indicate that the hydride transfer step is the chirality-determining step and the involvement of methanesulfonate anion (MsO−) in this reaction is of importance in the asymmetric hydrogenation of oximes catalyzed by A1 and B1. The calculated energy barriers for the hydride transfer steps without an MsO− anion are higher than those with an MsO− anion. The differences in Gibbs free energies between TSA5−1fR/TSA5−1fS and TSB5−1fR/TSB5−1fS are 13.8/13.2 (ΔΔG‡ = 0.6 kcal/mol) and 7.5/5.6 (ΔΔG‡ = 1.9 kcal/mol) kcal/mol for the hydride transfer step of substrate protonated oximes with E configuration (E−2a−H+) with MsO− anion to chiral hydroxylamines product R−3a/S−3a catalyzed by A1 and B1, respectively. According to the Curtin–Hammet principle, the major products are hydroxylamines S−3a for the reaction catalyzed by A1 and B1, which agrees well with the experimental results. This is due to the non-covalent interactions among the protonated substrate, MsO− anion and catalytic species. The hydrogen bond could not only stabilize the catalytic species, but also change the preference of stereoselectivity of this reaction.

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39

Charette, Bronte J., Joseph W. Ziller, and Alan F. Heyduk. "Exploring Ligand-Centered Hydride and H-Atom Transfer." Inorganic Chemistry 60, no. 7 (March 18, 2021): 5367–75. http://dx.doi.org/10.1021/acs.inorgchem.1c00351.

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40

Lee, In-Sook Han, Hyun Joo Kil, and Young Ran Ji. "Reactivities of acridine compounds in hydride transfer reactions." Journal of Physical Organic Chemistry 20, no. 7 (2007): 484–90. http://dx.doi.org/10.1002/poc.1182.

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41

Wu, Yun Dong, and K. N. Houk. "Theoretical transition structures for hydride transfer to methyleneiminium ion from methylamine and dihydropyridine. On the nonlinearity of hydride transfers." Journal of the American Chemical Society 109, no. 7 (April 1987): 2226–27. http://dx.doi.org/10.1021/ja00241a074.

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42

Wang, Yuanyuan, Qian Zhu, Yan Wei, Yanjun Gong, Chuncheng Chen, Wenjing Song, and Jincai Zhao. "Catalytic hydrodehalogenation over supported gold: Electron transfer versus hydride transfer." Applied Catalysis B: Environmental 231 (September 2018): 262–68. http://dx.doi.org/10.1016/j.apcatb.2018.03.032.

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43

Wang, Bin, Dhika Aditya Gandamana, Fabien Gagosz, and Shunsuke Chiba. "Diastereoselective Intramolecular Hydride Transfer under Brønsted Acid Catalysis." Organic Letters 21, no. 7 (March 18, 2019): 2298–301. http://dx.doi.org/10.1021/acs.orglett.9b00590.

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44

He, Bin, Phannarath Phansavath, and Virginie Ratovelomanana-Vidal. "Rhodium-catalyzed asymmetric transfer hydrogenation of 4-quinolone derivatives." Organic Chemistry Frontiers 7, no. 8 (2020): 975–79. http://dx.doi.org/10.1039/c9qo01514k.

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4-Quinolone derivatives were conveniently reduced to 1,2,3,4-tetrahydroquinoline-4-ols with excellent enantioselectivities through asymmetric transfer hydrogenation using a tethered rhodium complex and formic acid/triethylamine as the hydride source.

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45

Angle, Steven R., and Heather L. Mattson-Arnaiz. "Facile 1,3-hydride transfer in a cycloheptyl cation." Journal of the American Chemical Society 114, no. 25 (December 1992): 9782–86. http://dx.doi.org/10.1021/ja00051a009.

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46

Thorpe, Ian F., and Charles L. Brooks. "Conformational Substates Modulate Hydride Transfer in Dihydrofolate Reductase." Journal of the American Chemical Society 127, no. 37 (September 2005): 12997–3006. http://dx.doi.org/10.1021/ja053558l.

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47

Yuasa, Junpei, Shunsuke Yamada, and Shunichi Fukuzumi. "A Mechanistic Dichotomy in Scandium Ion-Promoted Hydride Transfer of an NADH Analogue: Delicate Balance between One-Step Hydride-Transfer and Electron-Transfer Pathways." Journal of the American Chemical Society 128, no. 46 (November 2006): 14938–48. http://dx.doi.org/10.1021/ja064708a.

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48

Liu, Li, Elizabeth S. Richards, and James M. Farrar. "Hydride transfer reaction dynamics of OD++C3H6." Journal of Chemical Physics 126, no. 24 (June 28, 2007): 244315. http://dx.doi.org/10.1063/1.2743025.

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49

Golub, Igor E., Oleg A. Filippov, Vasilisa A. Kulikova, Natalia V. Belkova, Lina M. Epstein, and Elena S. Shubina. "Thermodynamic Hydricity of Small Borane Clusters and Polyhedral closo-Boranes." Molecules 25, no. 12 (June 25, 2020): 2920. http://dx.doi.org/10.3390/molecules25122920.

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Анотація:

Thermodynamic hydricity (HDAMeCN) determined as Gibbs free energy (ΔG°[H]−) of the H− detachment reaction in acetonitrile (MeCN) was assessed for 144 small borane clusters (up to 5 boron atoms), polyhedral closo-boranes dianions [BnHn]2−, and their lithium salts Li2[BnHn] (n = 5–17) by DFT method [M06/6-311++G(d,p)] taking into account non-specific solvent effect (SMD model). Thermodynamic hydricity values of diborane B2H6 (HDAMeCN = 82.1 kcal/mol) and its dianion [B2H6]2− (HDAMeCN = 40.9 kcal/mol for Li2[B2H6]) can be selected as border points for the range of borane clusters’ reactivity. Borane clusters with HDAMeCN below 41 kcal/mol are strong hydride donors capable of reducing CO2 (HDAMeCN = 44 kcal/mol for HCO2−), whereas those with HDAMeCN over 82 kcal/mol, predominately neutral boranes, are weak hydride donors and less prone to hydride transfer than to proton transfer (e.g., B2H6, B4H10, B5H11, etc.). The HDAMeCN values of closo-boranes are found to directly depend on the coordination number of the boron atom from which hydride detachment and stabilization of quasi-borinium cation takes place. In general, the larger the coordination number (CN) of a boron atom, the lower the value of HDAMeCN.

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50

Alherz, Abdulaziz, Chern-Hooi Lim, James T. Hynes, and Charles B. Musgrave. "Predicting Hydride Donor Strength via Quantum Chemical Calculations of Hydride Transfer Activation Free Energy." Journal of Physical Chemistry B 122, no. 3 (January 5, 2018): 1278–88. http://dx.doi.org/10.1021/acs.jpcb.7b12093.

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