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Journal articles on the topic 'Radical pairs'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Woodward, J. R. "Radical Pairs in Solution." Progress in Reaction Kinetics and Mechanism 27, no. 3 (September 2002): 165–207. http://dx.doi.org/10.3184/007967402103165388.

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Radical pairs (RPs) are important reaction intermediates generated whenever two radicals encounter one another, a bond is cleaved homolytically or electron transfer between non-radical species takes place. The concept of a radical pair as a reaction intermediate is introduced and developed through simple pictorial analogies, indicating how RP behaviour is governed by interplay of spin and spatial motion. Such analogies are then extended to describe the experimental consequences of RPs in magnetic resonance and magnetochemistry experiments, including reference to the relevance of RPs in biological systems. Finally experimental techniques by which RPs can be observed directly are introduced and described in the context of the developed models.

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2

Angerhofer, Alexander, and Robert Bittl. "Radicals and Radical Pairs in Photosynthesis." Photochemistry and Photobiology 63, no. 1 (January 1996): 11–38. http://dx.doi.org/10.1111/j.1751-1097.1996.tb02989.x.

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3

Godloza, L., N. J. Groenewald, and W. A. Olivier. "Near-Ring Radicals and Class Pairs." Algebra Colloquium 12, no. 01 (March 2005): 101–12. http://dx.doi.org/10.1142/s100538670500009x.

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For near-ring ideal mappings ρ1 and ρ2, we investigate radical theoretical properties of and the relationship among the class pairs (ρ1: ρ2), [Formula: see text] and (ℛρ2: ℛρ1). Conditions on ρ1 and ρ2 are given for a general class pair to form a radical class of various types. These types include the Plotkin and KA-radical varieties. A number of examples are shown to motivate the suitability of the theory of Hoehnke-radicals over KA-radicals when radical pairs of near-rings are studied. In particular, it is shown that [Formula: see text] forms a KA-radical class, where [Formula: see text] denotes the class of completely prime near-rings and [Formula: see text] the class of 3-prime near-rings. This gives another near-ring generalization of the 2-primal ring concept. The theory of radical pairs are also used to show that in general the class of 3-semiprime near-rings is not the semisimple class of the 3-prime radical.

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4

Lubitz, Wolfgang, Friedhelm Lendzian, and Robert Bittl. "Radicals, Radical Pairs and Triplet States in Photosynthesis." Accounts of Chemical Research 35, no. 5 (May 2002): 313–20. http://dx.doi.org/10.1021/ar000084g.

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5

Lee, Alpha A., Jason C. S. Lau, Hannah J. Hogben, Till Biskup, Daniel R. Kattnig, and P. J. Hore. "Alternative radical pairs for cryptochrome-based magnetoreception." Journal of The Royal Society Interface 11, no. 95 (June 6, 2014): 20131063. http://dx.doi.org/10.1098/rsif.2013.1063.

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There is growing evidence that the remarkable ability of animals, in particular birds, to sense the direction of the Earth's magnetic field relies on magnetically sensitive photochemical reactions of the protein cryptochrome. It is generally assumed that the magnetic field acts on the radical pair [FAD •− TrpH • + ] formed by the transfer of an electron from a group of three tryptophan residues to the photo-excited flavin adenine dinucleotide cofactor within the protein. Here, we examine the suitability of an [FAD •− Z • ] radical pair as a compass magnetoreceptor, where Z • is a radical in which the electron spin has no hyperfine interactions with magnetic nuclei, such as hydrogen and nitrogen. Quantum spin dynamics simulations of the reactivity of [FAD •− Z • ] show that it is two orders of magnitude more sensitive to the direction of the geomagnetic field than is [FAD •− TrpH • + ] under the same conditions (50 µT magnetic field, 1 µs radical lifetime). The favourable magnetic properties of [FAD •− Z • ] arise from the asymmetric distribution of hyperfine interactions among the two radicals and the near-optimal magnetic properties of the flavin radical. We close by discussing the identity of Z • and possible routes for its formation as part of a spin-correlated radical pair with an FAD radical in cryptochrome.

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6

Yakunin, I. N., and V. L. Berdinskii. "The chemical zeno effect in exchange-coupled radical Pairs: 1. Triplet radical pairs." Russian Journal of Physical Chemistry B 4, no. 2 (April 2010): 210–16. http://dx.doi.org/10.1134/s1990793110020053.

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7

Casal, H. L., D. Griller, F. W. Hartstock, R. Kolt, D. J. Northcott, J. M. Park, and D. D. M. Wayner. "Radical pairs in urea channels." Journal of Physical Chemistry 91, no. 9 (April 1987): 2235–36. http://dx.doi.org/10.1021/j100293a004.

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8

Bagryansky, Victor A., Vsevolod I. Borovkov, and Yuri N. Molin. "Quantum beats in radical pairs." Russian Chemical Reviews 76, no. 6 (June 30, 2007): 493–506. http://dx.doi.org/10.1070/rc2007v076n06abeh003715.

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9

Merkley, Nadine, Paul C. Venneri, and John Warkentin. "Cyclopropanation of benzylidenemalononitrile with dialkoxycarbenes and free radical rearrangement of the cyclopropanes." Canadian Journal of Chemistry 79, no. 3 (March 1, 2001): 312–18. http://dx.doi.org/10.1139/v01-017.

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Thermolysis of 2-cinnamyloxy-2-methoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline (1a) and the analogous 2-benzyloxy-2-methoxy compound (1b) at 110°C, in benzene containing benzylidenemalononitrile, afforded products of apparent regiospecific addition of methoxycarbonyl and cinnamyl (or benzyl) radicals to the double bond. When the thermolysis of 1a was run with added TEMPO, methoxycarbonyl and cinnamyl radicals were captured. Thermolysis of the 2,2-dibenzyloxy analogue (1c) in the presence of benzylidenemalononitrile gave an adduct that is formally the product of addition of benzyloxycarbonyl and benzyl radicals to the double bond. In this case, a radical addition mechanism could be ruled out, because the rate constant for decarboxylation of benzyloxycarbonyl radicals is very large. A mechanism that fits all of the results is predominant cyclopropanation of benzylidenemalononitrile by the dialkoxycarbenes derived from the oxadiazolines, in competition with fragmentation of the carbenes to radical pairs. The cyclopropanes so formed then undergo homolytic ring-opening to the appropriate diradicals. Subsequent β-scission of the diradicals to afford radical pairs, and coupling of those pairs, gives the final products. Thus, both carbene and radical chemistry are involved in the overall processes.Key words: cyclopropane, dialkoxycarbene, β-scission, oxadiazoline, radical.

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10

Yakunin, I. N., and V. L. Berdinskii. "The chemical zeno effect in exchange-bounded radical pairs: 2. Singlet and random radical pairs." Russian Journal of Physical Chemistry B 4, no. 3 (June 2010): 384–90. http://dx.doi.org/10.1134/s1990793110030048.

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11

Lubitz, Wolfgang, Friedhelm Lendzian, and Robert Bittl. "ChemInform Abstract: Radicals, Radical Pairs and Triplet States in Photosynthesis." ChemInform 33, no. 32 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200232299.

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12

Tarasov, Valery F., Naresh D. Ghatlia, Nikolai I. Avdievich, and Nicholas J. Turro. "Exchange Interaction in Micellized Radical Pairs*." Zeitschrift für Physikalische Chemie 1, Part_2 (January 1992): 227–44. http://dx.doi.org/10.1524/zpch.1992.1.part_2.227.

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13

Tarasov, Valery F., Naresh D. Ghatlia, Nikolai I. Avdievich, and Nicholas J. Turro. "Exchange Interaction in Micellized Radical Pairs*." Zeitschrift für Physikalische Chemie 182, Part_1_2 (January 1993): 227–44. http://dx.doi.org/10.1524/zpch.1993.182.part_1_2.227.

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14

Wu, Zhuang, Changyun Chen, Jie Liu, Yan Lu, Jian Xu, Xiangyang Liu, Ganglong Cui, et al. "Caged Nitric Oxide–Thiyl Radical Pairs." Journal of the American Chemical Society 141, no. 8 (February 13, 2019): 3361–65. http://dx.doi.org/10.1021/jacs.8b12746.

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15

Woodward, Jonathan R., Timothy J. Foster, Alex R. Jones, Adrian T. Salaoru, and Nigel S. Scrutton. "Time-resolved studies of radical pairs." Biochemical Society Transactions 37, no. 2 (March 20, 2009): 358–62. http://dx.doi.org/10.1042/bst0370358.

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The effect of magnetic fields on chemical reactions through the RP (radical pair) mechanism is well established, but there are few examples, in the literature, of biological reactions that proceed through RP intermediates and show magnetic field-sensitivity. The present and future relevance of magnetic field effects in biological reactions is discussed.

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16

Sailer, Christian F., and Eberhard Riedle. "Photogeneration and reactions of benzhydryl cations and radicals: A complex sequence of mechanisms from femtoseconds to microseconds." Pure and Applied Chemistry 85, no. 7 (June 30, 2013): 1487–98. http://dx.doi.org/10.1351/pac-con-13-04-01.

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Benzhydryl radicals and cations are reactive intermediates central to the understanding of organic reactivity. They can be generated from benzhydryl halides by UV irradiation. We performed transient absorption (TA) measurements over the range from femtoseconds to microseconds to unravel the complete reaction scheme. The 290–720-nm probe range allows the unambiguous monitoring of all fragments. The appearance of the radical is delayed to the optical excitation, the onset of the cation signal is found even later. Ab initio calculations show that this non-rate behavior in the 100 fs range is due to wavepacket motion from the Franck–Condon region to two distinct conical intersections. The rise of the optical signal with a quasi-exponential time of 300 fs is assigned to the planarization and solvation of the photoproducts. The bond cleavage predominantly generates radical pairs. A subsequent electron transfer (ET) transforms radical pairs into ion pairs. Due to the broad interradical distance distribution and the distance dependence, the ET is strongly non-exponential. Part of the ion pairs recombine geminately. The ET and the recombination are terminated by the depletion of close pairs and diffusional separation. The remaining free radicals and cations undergo further reactions in the nanosecond to microsecond regime.

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17

Lipson, Matthew, Ashok A. Deniz, and Kevin S. Peters. "The sub-picosecond dynamics of diphenylmethylchloride ion pairs and radical pairs." Chemical Physics Letters 288, no. 5-6 (May 1998): 781–84. http://dx.doi.org/10.1016/s0009-2614(98)00345-5.

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18

Lebedkin, S. F., A. D. Klimov, and V. N. Emokhonov. "Effect of deprotonation of ion-radical pairs on yield of radicals." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 39, no. 6 (June 1990): 1160–63. http://dx.doi.org/10.1007/bf00962376.

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19

Gladkikh, V. S., G. Angulo, and A. I. Burshtein. "Production of Free Radicals and Triplets from Contact Radical Pairs and from Photochemically Generated Radical Ions." Journal of Physical Chemistry A 111, no. 18 (May 2007): 3458–64. http://dx.doi.org/10.1021/jp068375f.

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20

Dasgupta, Ayan, Emma Richards, and Rebecca L. Melen. "Frustrated Radical Pairs: Insights from EPR Spectroscopy." Angewandte Chemie 133, no. 1 (November 17, 2020): 53–65. http://dx.doi.org/10.1002/ange.202010633.

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21

Dasgupta, Ayan, Emma Richards, and Rebecca L. Melen. "Frustrated Radical Pairs: Insights from EPR Spectroscopy." Angewandte Chemie International Edition 60, no. 1 (November 17, 2020): 53–65. http://dx.doi.org/10.1002/anie.202010633.

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22

Harrison, Norma, and Martyn C. R. Symons. "Detection of radical pairs in glassy systems." Journal of the Chemical Society, Faraday Transactions 89, no. 1 (1993): 59. http://dx.doi.org/10.1039/ft9938900059.

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23

Macernis, Mindaugas. "On the Dimers Stability of Allicin and Its Derivatives Interacting with AT, GC, and DNA Bridge: DFT Study." Journal of Chemistry 2017 (2017): 1–11. http://dx.doi.org/10.1155/2017/1428508.

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Allicin and its derivatives are physiologically active molecules with many potential health benefits. It is not clear if they have a direct effect on DNA or protein. In order to elucidate the allicin and its derivatives’ effect on DNA base pairs, we investigated various complexes of base pair and its bridge with an allicin and its derivatives. The investigated allicin derivatives were (E)-Ajoene, (Z)-Ajoene, Amz121, and Bmz73 radicals. The DFT calculation results revealed that the investigated molecules would favor binding to bridge of the base pairs instead of directly affecting the base pairs. The Bmz73 radical could break DNA by change bonding in it because the Bmz73 radical significantly affected the P-O bond of the bridge of base pair.

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24

Zarei, Mohammad, Abdolvahab Seif, Khaled Azizi, Mohanna Zarei, and Jamil Bahrami. "Effect of phenolic radicals on the geometry and electronic structure of DNA base pairs: computational study." International Journal of Modern Physics C 27, no. 10 (August 29, 2016): 1650119. http://dx.doi.org/10.1142/s0129183116501199.

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In this paper, we show the reaction of a hydroxyl, phenyl and phenoxy radicals with DNA base pairs by the density functional theory (DFT) calculations. The influence of solvation on the mechanism is also presented by the same DFT calculations under the continuum solvation model. The results showed that hydroxyl, phenyl and phenoxy radicals increase the length of the nearest hydrogen bond of adjacent DNA base pair which is accompanied by decrease in the length of furthest hydrogen bond of DNA base pair. Also, hydroxyl, phenyl and phenoxy radicals influenced the dihedral angle between DNA base pairs. According to the results, hydrogen bond lengths between AT and GC base pairs in water solvent are longer than vacuum. All of presented radicals influenced the structure and geometry of AT and GC base pairs, but phenoxy radical showed more influence on geometry and electronic properties of DNA base pairs compared with the phenyl and hydroxyl radicals.

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25

Markovic, Dejan. "Photochemistry of aromatic ketones in sodium dodecyl sulphate micelles in the presence of unsaturated fatty acids." Journal of the Serbian Chemical Society 69, no. 2 (2004): 107–15. http://dx.doi.org/10.2298/jsc0402107m.

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Laser-flash photolysis has been employed to characterize the behaviour of the free radicals created in the photochemical reaction of benzophenone (BZP), as well as of its lipoidal derivative, benzophenone-4-heptyl-4?-pentanoic acid (BHPA), with chosen unsaturated fatty acids in sodium dodecyl sulphate micelles. The calculated rate constants were used to study the "cage effect" i.e., the recombination of the created radical-pairs (BZP, BHPA ketyl radical - lipid radical) inside the highly limited space of the SDS micelles. The "cage effect" appears to be the dominant event inside SDS micelles, dependent on the structure of both the reactants-precursors. The fractions of the initially created radical-pairs which escape the "cage effect" and exit into the surrounding aqueous phase do not exceed 16 %. This fact is of enormous importance for the self-control of the pathogenic process of lipid peroxidation.

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26

Step, Eugene N., Anatolii L. Buchachenko, and Nicholas J. Turro. "Paramagnetic Interactions of Triplet Radical Pairs with Nitroxide Radicals: An "Antiscavenging" Effect." Journal of the American Chemical Society 116, no. 12 (June 1994): 5462–66. http://dx.doi.org/10.1021/ja00091a059.

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27

Paulus, Bernd, Csaba Bajzath, Frédéric Melin, Lorenz Heidinger, Viktoria Kromm, Christoph Herkersdorf, Ulrike Benz, et al. "Spectroscopic characterization of radicals and radical pairs in fruit fly cryptochrome - protonated and nonprotonated flavin radical-states." FEBS Journal 282, no. 16 (April 30, 2015): 3175–89. http://dx.doi.org/10.1111/febs.13299.

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28

Erker, Gerhard. "Frustrated Lewis pairs: Some recent developments." Pure and Applied Chemistry 84, no. 11 (August 31, 2012): 2203–17. http://dx.doi.org/10.1351/pac-con-12-04-07.

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The chemistry of some reactive frustrated Lewis pairs (FLPs) is reported. This includes intramolecular P/B and N/B FLPs, some of which were used as catalysts for the hydrogenation of electron-rich olefin substrates. Some advanced intermolecular FLPs are reported, which includes systems derived from very bulky alkenyl boranes obtained from 1,1-carboboration reactions of 1-alkynes with tris(pentafluorophenyl)borane. Some such systems activate dihydrogen and transfer the resulting proton/hydride pair even to some electron-poor alkynes. Eventually, we report on the reaction of our intramolecular ethylene-bridged P/B FLP with nitric oxide (NO). N,B-addition of the P-Lewis base/B-Lewis acid combination is observed to form a new type of a persistent aminoxyl radical. Some of the chemistry of the new FLP-NO radicals is presented and discussed.

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29

Goez, Martin, Isabell Frisch, and Ingo Sartorius. "Electron and hydrogen self-exchange of free radicals of sterically hindered tertiary aliphatic amines investigated by photo-CIDNP." Beilstein Journal of Organic Chemistry 9 (February 26, 2013): 437–46. http://dx.doi.org/10.3762/bjoc.9.46.

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The photoreactions of diazabicyclo[2,2,2]octane (DABCO) and triisopropylamine (TIPA) with the sensitizers anthraquinone (AQ) and xanthone (XA) or benzophenone (BP) were investigated by time-resolved photo-CIDNP (photochemically induced dynamic nuclear polarization) experiments. By varying the radical-pair concentration, it was ensured that these measurements respond only to self-exchange reactions of the free amine-derived radicals (radical cations DH • + or α-amino alkyl radicals D • ) with the parent amine DH; the acid–base equilibrium between DH • + and D • also plays no role. Although the sensitizer does not at all participate in the observed processes, it has a pronounced influence on the CIDNP kinetics because the reaction occurs through successive radical pairs. With AQ, the polarizations stem from the initially formed radical-ion pairs, and escaping DH • + then undergoes electron self-exchange with DH. In the reaction sensitized with XA (or BP), the polarizations arise in a secondary pair of neutral radicals that is rapidly produced by in-cage proton transfer, and the CIDNP kinetics are due to hydrogen self-exchange between escaping D • and DH. For TIPA, the activation parameters of both self-exchange reactions were determined. Outer-sphere reorganization energies obtained with the Marcus theory gave very good agreement between experimental and calculated values of ∆G ‡ 298.

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30

Kelly, DP, AK Serelis, DH Solomon, and PE Thompson. "The Cross-Reaction Between 1-Methoxycarbonyl-1-Methylethyl and 1-Butoxycarbonyl-1-Methylethyl: Simultaneous Generation of Unlike Radicals From an Unsymmetrical Azo Precursor." Australian Journal of Chemistry 40, no. 10 (1987): 1631. http://dx.doi.org/10.1071/ch9871631.

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The title radicals (1a) and (1b) were generated simultaneously by thermolysis of the unsymmetrical diazene, butyl methyl azoisobutyrate (2d). In the presence of the radical scavenger 2,2,6,6- tetramethylpiperidin-1-yloxyl (4) the products of the geminate cross-reaction show that 45% of radical pairs react by combination and 55% by disproportionation. The disproportionation reaction shows a slight preference for hydrogen transfer from the butyl ester (lb) to the methyl ester (la) radical. In the absence of scavenger (4), the encounter reactions of the two radicals show a slight preference for the cross-reaction over the two self-reactions which is most likely largely due to the imbalance in radical concentrations caused by the greater reactivity toward addition to olefins of the methyl ester radical.

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31

Wang, Mei, Jing Zhao, Laibin Zhang, Xiyu Su, Hanlei Su, and Yuxiang Bu. "Intriguing radical–radical interactions among double-electron oxidized adenine–thymine base pairs." Chemical Physics Letters 619 (January 2015): 223–29. http://dx.doi.org/10.1016/j.cplett.2014.11.027.

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32

Hansen, Martin J., and J. Boiden Pedersen. "Recombination yield of initially separated geminate radical pairs." Chemical Physics Letters 360, no. 5-6 (July 2002): 453–58. http://dx.doi.org/10.1016/s0009-2614(02)00726-1.

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33

Casal, H. L., D. Griller, R. J. Kolt, F. W. Hartstock, D. M. Northcott, J. M. Park, and D. D. M. Wayner. "Behavior of alkyl radical pairs in urea channels." Journal of Physical Chemistry 93, no. 4 (February 1989): 1666–70. http://dx.doi.org/10.1021/j100341a094.

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34

Scott, T. W., and S. N. Liu. "Picosecond geminate recombination of phenylthiyl free-radical pairs." Journal of Physical Chemistry 93, no. 4 (February 1989): 1393–96. http://dx.doi.org/10.1021/j100341a042.

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35

Roth, Heinz D. "Recombination of radical ion pairs of triplet multiplicity." Journal of Photochemistry and Photobiology C: Photochemistry Reviews 2, no. 2 (December 2001): 93–116. http://dx.doi.org/10.1016/s1389-5567(01)00013-2.

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36

Lewis, Frederick D. "Proton-transfer reactions of photogenerated radical ion pairs." Accounts of Chemical Research 19, no. 12 (December 1986): 401–5. http://dx.doi.org/10.1021/ar00132a004.

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37

Nakajima, Satoru, Kimio Akiyama, Kiyohiko Kawai, Tadao Takada, Tadaaki Ikoma, Tetsuro Majima, and Shozo Tero-Kubota. "Spin-Correlated Radical Pairs in Synthetic Hairpin DNA." ChemPhysChem 8, no. 4 (March 12, 2007): 507–9. http://dx.doi.org/10.1002/cphc.200600621.

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38

Weller, Professor A. "Exciplexes and Radical Pairs in Photochemical Electron Transfer." Bulletin des Sociétés Chimiques Belges 91, no. 5 (September 1, 2010): 353. http://dx.doi.org/10.1002/bscb.19820910512.

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39

Player, Thomas C., and P. J. Hore. "Viability of superoxide-containing radical pairs as magnetoreceptors." Journal of Chemical Physics 151, no. 22 (December 14, 2019): 225101. http://dx.doi.org/10.1063/1.5129608.

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40

Roth, Heinz D. "Biradicals by triplet recombination of radical ion pairs." Photochemical & Photobiological Sciences 7, no. 5 (2008): 540. http://dx.doi.org/10.1039/b800524a.

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41

Bittl, Robert, and Stefan Weber. "Transient radical pairs studied by time-resolved EPR." Biochimica et Biophysica Acta (BBA) - Bioenergetics 1707, no. 1 (February 2005): 117–26. http://dx.doi.org/10.1016/j.bbabio.2004.03.012.

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42

Buckley, C. D., D. A. Hunter, P. J. Hore, and K. A. McLauchlan. "Electron spin resonance of spin-correlated radical pairs." Chemical Physics Letters 135, no. 3 (April 1987): 307–12. http://dx.doi.org/10.1016/0009-2614(87)85162-x.

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43

Morozov, V. A., A. B. Doktorov, and R. Z. Sagdeev. "Theory of multiquantum SNP spectra of radical pairs." Chemical Physics 179, no. 3 (February 1994): 287–302. http://dx.doi.org/10.1016/0301-0104(94)87008-x.

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44

Roth, Heinz D. "Return electron transfer in radical ion pairs of triplet multiplicity." Pure and Applied Chemistry 77, no. 6 (January 1, 2005): 1075–85. http://dx.doi.org/10.1351/pac200577061075.

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Return electron transfer (RET) in radical ion pairs may populate the reagent ground states or, in the case of triplet pairs, one reagent triplet state. The efficiency of triplet RET is governed by the free energies of singlet and triplet RET and by the topologies of the potential surfaces of parent molecules, radical ions, and accessible triplet states or biradicals. RET in triplet radical ion pairs is exemplified for two distinct relationships between the three potential surfaces.

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45

Godloza, L., N. J. Groenewald, and W. A. Olivier. "On Jacobson Near-rings and Special Radicals." Algebra Colloquium 14, no. 01 (March 2007): 1–14. http://dx.doi.org/10.1142/s1005386707000028.

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In this paper, we construct special radicals using class pairs of near-rings. We establish necessary conditions for a class pair to be a special radical class. We then define Jacobson-type near-rings and show that in most cases the class of all near-rings of this type is a special radical class. Subsequently, we investigate the relationship between each Jacobson-type near-ring and the corresponding matrix near-ring.

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46

Merkley, Nadine, and John Warkentin. "Benzyloxy(4-substituted benzyloxy)carbenes. Generation from oxadiazolines and fragmentation to radical pairs in solution." Canadian Journal of Chemistry 78, no. 7 (July 1, 2000): 942–49. http://dx.doi.org/10.1139/v00-078.

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Thermolysis of 2,2-dibenzyloxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline in benzene at 110°C leads to dibenzyloxycarbene. The carbene was trapped with tert-butyl alcohol to afford dibenzyl-tert-butyl orthoformate. In the absence of a trapping agent for the carbene, it fragmented to benzyloxycarbonyl and benzyl radicals, as shown by trapping the latter with TEMPO. In the absence of both TEMPO and tert-butyl alcohol, the radicals were partitioned between coupling to benzyl phenylacetate and decarboxylation, with subsequent formation of bibenzyl. The preferred sense of fragmentation of the analogous carbenes from benzyloxy-(p-substituted-benzyloxy)carbenes was determined by comparing the yields of the two possible esters, ArCH2O(CO)CH2Ph and PhCH2O(CO)CH2Ar. It was found that an electron-withdrawing group in the para position favoured fragmentation to the benzylic radical containing that group. A Hammett plot of the data gave a best fit with σ- substituent constants (r = 0.994, ρ(PhH, 110°C) = 0.7) suggesting that the fragmentation involves charge separation in the sense that increases electron density on the group that is becoming a benzylic radical and decreases electron density on the carbonyl group that is becoming the benzyloxycarbonyl radical.Key words: carbene, dibenzyloxycarbene, fragmentation, substituent effect, radical pair, TEMPO.

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47

Schupfner, Robert, and Adolf Müller. "Temperature-Dependent ESR Studies of Radical Pairs in Single Crystals of Barbituric Acid." Zeitschrift für Naturforschung C 44, no. 9-10 (October 1, 1989): 849–56. http://dx.doi.org/10.1515/znc-1989-9-1026.

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Abstract:

Abstract After irradiation of single crystals of barbituric acid with X-rays at 77 K different types of radical pairs are found, which are com posed of only one type of monoradical. The properties of radical pairs of the unpaired electrons are studied using frequency-variable ESR methods at various temperatures. In addition to the radical pairs AD and BC two further pairs A′D′ and XY were identified. Measurements of the fine structure parameter D showed a linear temperature dependence in some regions between 77 K and 290 K. At 240 K the radical pairs AD and A′D′ changed reversibly into A*D* and this pair remained stable up to 290 K. A level anticrossing effect was observed with the pair AD. The exchange energy J between the singlet state and the triplet state was determined as -(15.1 ± 0.6) GHz at 77 K and its temperature coefficient as -(3.8 ± 0.8) × 10-3K-1.

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48

Benniston, Andrew C., Anthony Harriman, Douglas Philp, and J. Fraser Stoddart. "Charge recombination in cyclophane-derived, intimate radical ion pairs." Journal of the American Chemical Society 115, no. 12 (June 1993): 5298–99. http://dx.doi.org/10.1021/ja00065a052.

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49

Soltani, Yashar, Ayan Dasgupta, Theodore A. Gazis, Darren M. C. Ould, Emma Richards, Ben Slater, Katarina Stefkova, et al. "Radical Reactivity of Frustrated Lewis Pairs with Diaryl Esters." Cell Reports Physical Science 1, no. 2 (February 2020): 100016. http://dx.doi.org/10.1016/j.xcrp.2020.100016.

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50

Loos, Ottmar. "The nil radical in jordan pairs over uncountable fields." Communications in Algebra 23, no. 9 (January 1995): 3541–43. http://dx.doi.org/10.1080/00927879508825414.

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