In general, the electron will prefer (Aufbau principle) to enter the lowest energy antibonding molecular orbital (LUMO). 3D image storage in photopolymer/ZnS nanocomposites tailored by “photoinitibitor”. This interesting result obtains because, in the assumed kind of nonpolar system, the filling of the BMO’s evidently results in Qi = 0 at each position. Alkali metals reduce benzophenone to the deeply blue colored radical anion, diphenylketyl:. This anion is then protonated (by ammonia or an alcohol which has been added to the solvent) to yield 2-butene. Scheme 10. Addition of a single electron to a neutral (uncharged) molecule generates a unique chemical species, called an, (or radical anion by some) that simultaneously has a unit of negative charge and an unpaired electron. Spin trapping of radicals formed during radiolysis of aqueous solutions. Distillation of the solvent then yields a very pure sample. Nature, 2010, 468: 80–83, Ozaki M, Kato J, Kawata S. Surface-plasmon holography with white-light illumination. This molecular entity is very unstable and appears in chemical reactions as a reactive intermediate. Hopefully you have already calculated the charge. in ethane). Chem Phys Lett, 2009, 475: 235–239, Christensen SK, Chiappelli MC, Hayward RC. Electrically switchable light transmittance of epoxy-mercaptan polymer/nematic liquid crystal composites with controllable microstructures. Science, 2009, 324: 913–917, Frisch MJ, Trucks GW, Schlegel HB, et al. https://www.definitions.net/definition/ketyl. His current interest focuses on photopolymerization mechanism and applications. Macromolecules, 2012, 45: 5237–5246, Li MD, Du Y, Chuang YP, et al. - 35.164.102.12. The blue benzophenone anion radical is very commonly seen in the organic laboratory as a drying agent for ethereal solvents such as tetrahydrofuran (THF). Sodium reduces benzophenone to the soluble ketyl radical, which reacts quickly with the water and oxygen dissolved in the solvent. Polymer, 2019, 160: 53–64, Zhao D, Zhou W, Cui X, et al. Acta Polym Sin, 2017, 48: 1557–1573, Peng H, Chen G, Ni M, et al. Wallingford CT: Gaussion, Inc. 2013, Yamaji M, Oshima J, Hidaka M. Verification of the electron/proton coupled mechanism for phenolic H-atom transfer using a triplet π,π* carbonyl. Usually this is prepared by reaction of biphenyl with lithium metal, often in THF solvent. China Mater. Scheme 11. Another mesomeric structure has the radical position on carbon and the negative charge on oxygen. J Org Chem, 1986, 51: 1138–1140, Sargent FP, Gardy EM. Starting with a flask of already rather pure and anhydrous solvent (obtained commercially),  a small amount of benzophenone is added followed by the addition of potassium metal. Recall that the formation of cyclobutanes by cycloaddition of two alkene molecules is extremely difficult and, for practical purposes, quite useless. In Principles of Polymerization, 4th ed. A ketyl group in organic chemistry is an anion radical that contains a group =C-O• in which an oxygen radical is bonded directly to carbon, negatively charged. Nature, 1948, 161: 777–778, CAS  The Cyclooctatetraene Anion Radical. It is interesting to note the relative stability of the anion radicals of aromatic system, even though the addition of an electron to an ABMO diminishes the net bonding of the system. The anion radical, however, is a 9 electron system and although not aromatic, it is not antiaromatic either. Phototriggered base proliferation: A highly efficient domino reaction for creating functionally photo-screened materials. As it turns out the anion radical of this system is actually planar and a true cyclic, conjugated system. Effect of ketyl radical on the structure and performance of holographic polymer/liquid-crystal composites, https://doi.org/10.1007/s40843-019-9580-y. Birch reduction of naphthalene by sodium in liquid ammonia, containing tert-butyl alcohol. Reduction of a conjugated diene with alkali metal in liquid ammonia. Needless to say, if a polar functionality such as a ketone function is present, the filling of the BMO’s does result in non-zero charge accumulations at most atoms, so that both the SOMO and the BMO’s contribute to the overall charge densities. Addition of a single electron to a neutral (uncharged) molecule generates a unique chemical species, called an anion radical (or radical anion by some) that simultaneously has a unit of negative charge and an unpaired electron. Reactions Involving Ketyl Radicals 4-Hydroxybutyryl-CoA dehydratase Buckel, W.; Golding, B. T. Annu. Reduction of the resulting radical to an anion is followed by protonation, also at the alpha position. These electrons are available to transfer to an ABMO of an organic molecule. Spin trapping in electrochemistry. Clickable nucleic acids: Sequence-controlled periodic copolymer/oligomer synthesis by orthogonal thiol-X reactions. In the context of the resulting anion radical, this same MO then becomes the, (singly occupied MO of a radical species). The resulting ketyl radical combines with an alkyne to form a vinyl radical, which is oxidized by the Mn catalyst to form the vinyl iodide product and regenerate Mn(CO) 5. This can be accomplished, in many cases, by simply treatment with an alkali metal (which makes the alkali metal cation the counterion to the anion radical).

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