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Journal articles on the topic 'Radical clock'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

Nevill, S. M., and J. A. Pincock. "The design of radical clocks to probe the reactivity of the intermediates in arylmethyl ester photochemistry." Canadian Journal of Chemistry 75, no. 2 (1997): 232–47. http://dx.doi.org/10.1139/v97-027.

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The photochemistry in methanol of the esters 1–6was examined. These reactions normally proceed through radical pairs that result from homolytic cleavage of the carbon–oxygen bond in the excited singlet state. Each of the esters was designed to probe the intervention and reactivity of the substituted arylmethyl radical by incorporating a potential radical clock at the carbon of the reactive bond. For esters 1–5, the products isolated indicated that the radical clock was not reactive enough to compete with the very rapid alternate processes of the radical pair, namely, electron transfer to form

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2

Mai-Linde, Yasemin, and Torsten Linker. "Radical Clock Probes to Determine Carbohydrate Radical Stabilities." Organic Letters 22, no. 4 (2020): 1525–29. http://dx.doi.org/10.1021/acs.orglett.0c00111.

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3

Kunka, Cheryl P. A., and John Warkentin. "Facile 5-endo ring closures to the azo group. A free radical synthesis of indazoles." Canadian Journal of Chemistry 68, no. 4 (1990): 575–80. http://dx.doi.org/10.1139/v90-088.

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Five 1-alkyl-3-methylindazoles were prepared by treatment of 1-(2-bromophenyl)-1-methoxy-1-(2-alkylazo)ethanes with tri-n-butyl stannane and AIBN at 80 °C in benzene. Yields in the radical cyclization step ranged from 39 to 92%. 1-Phenyl-3-methylindazole was prepared by an analogous route but in very poor yield (<5%). Rate constants for the 5-endo radical closures [Formula: see text], estimated by the radical clock method, were 5.2 × 109 s−1 and 9.2 × 108 s−1 for two of the alkyl systems. Rate constants for analogous 5-endo cyclizations of aryl radicals onto C—C double bonds are much smalle

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4

Buckmelter, Alexandre J., Angie I. Kim, and Scott D. Rychnovsky. "Conformational Memory in Enantioselective Radical Reductions and a New Radical Clock Reaction." Journal of the American Chemical Society 122, no. 39 (2000): 9386–90. http://dx.doi.org/10.1021/ja002068k.

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5

He, Xiang, та Paul R. Ortiz de Montellano. "α- and β-Thujone Radical Rearrangements and Isomerizations. A New Radical Clock". Journal of Organic Chemistry 69, № 17 (2004): 5684–89. http://dx.doi.org/10.1021/jo0493267.

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6

Hollis, R., L. Hughes, V. W. Bowry, and K. U. Ingold. "Calibration of a fast benzylic radical clock reaction." Journal of Organic Chemistry 57, no. 15 (1992): 4284–87. http://dx.doi.org/10.1021/jo00041a040.

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7

Wang, Wenbo, Haotian Lu, Mengsi Zhang, et al. "Synthesis of maleimide-based enediynes with cyclopropane moieties for enhanced cytotoxicity under normoxic and hypoxic conditions." Journal of Materials Chemistry B 9, no. 22 (2021): 4502–9. http://dx.doi.org/10.1039/d1tb00142f.

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Maleimide-based enediynes with cyclopropane moieties show enhanced radical character by taking advantage of radical clock reactions. They are highly effecient antitumor agents under both normoxic and hypoxic conditions.

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8

Jewell, Deborah Rae, Lukose Mathew, and John Warkentin. "Rate constant for chlorine abstraction from CCl4 by the 5-hexenyl radical." Canadian Journal of Chemistry 65, no. 2 (1987): 311–15. http://dx.doi.org/10.1139/v87-052.

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Cyclization of the 5-hexenyl free radical to the cyclopentylmethyl free radical was used to clock chlorine atom abstraction by 5-hexenyl from carbon tetrachloride in solution. The source of 5-hexenyl radicals was 5-hexenyl[1-hydroxy-1-methyl-ethyl]diazene ((CH3)2C(OH)N=N(CH2)4CH=CH2), which decomposes thermally in CCl4 by a radical chain mechanism to afford chloroform, acetone, nitrogen, 6-chloro-1-hexene, cyclopentylchloromethane, 1-hexene, and methylcyclopentane as primary products. 6-Chloro-1-hexene is converted, in part, to a secondary product, 1,1,1,3,7-pentachloroheptane, by radical chai

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9

Lu, Qingyi, and William C. Agosta. "A radical clock reaction in the photochemistry of an acylpyrazine." Tetrahedron Letters 37, no. 48 (1996): 8629–32. http://dx.doi.org/10.1016/s0040-4039(96)02023-0.

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10

Bowry, V., J. Lusztyk, and K. U. Ingold. "Calibration of very fast alkyl radical 'clock' rearrangements using nitroxides." Pure and Applied Chemistry 62, no. 2 (1990): 213–16. http://dx.doi.org/10.1351/pac199062020213.

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11

Huang, Hui, Wei-Chen Chang, Geng-Min Lin, et al. "Mechanistic Consequences of Chiral Radical Clock Probes: Analysis of the Mononuclear Non-Heme Iron Enzyme HppE with 2-Hydroxy-3-methylenecyclopropyl Radical Clock Substrates." Journal of the American Chemical Society 136, no. 8 (2014): 2944–47. http://dx.doi.org/10.1021/ja4100035.

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12

Jiang, Yongying, та Paul R. Ortiz de Montellano. "Cooperative Effects on Radical Recombination in CYP3A4-Catalyzed Oxidation of the Radical Clock β-Thujone". ChemBioChem 10, № 4 (2009): 650–53. http://dx.doi.org/10.1002/cbic.200800772.

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13

Rudolph, Andreas, and Alan C. Weedon. "Radical clocks as probes of 1,4-biradical intermediates in the photochemical cycloaddition reactions of 2-cyclopentenone with alkenes." Canadian Journal of Chemistry 68, no. 9 (1990): 1590–97. http://dx.doi.org/10.1139/v90-245.

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The products of the photochemical reaction of 2-cyclopentenone with 1,6-heptadiene and with vinylcyclopropane have been examined. With 1,6-heptadiene the products were cyclobutanes, which arise from 2 + 2 photocycloaddition between the cyclopentenone carbon–carbon double bond and one of the two terminal double bonds of the heptadiene. The 1,4-biradical that is an intermediate in this reaction contains a derivative of a 1-hexenyl radical; no products derived from cyclization of this intermediate to a cyclopentylmethyl radical were observed. With vinylcyclopropane some of the products isolated a

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14

Vanni, Raffaella, Simon J. Garden, Jeffrey T. Banks, and Keith U. Ingold. "Mechanism of hydroxylation of alkanes by dimethyldioxirane. A radical-clock study." Tetrahedron Letters 36, no. 44 (1995): 7999–8002. http://dx.doi.org/10.1016/0040-4039(95)01666-6.

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15

Chatgilialoglu, C., V. I. Timokhin, and M. Ballestri. "One-Carbon Ring Expansion in Cyclopentanones as a Free-Radical Clock." Journal of Organic Chemistry 63, no. 4 (1998): 1327–29. http://dx.doi.org/10.1021/jo9716338.

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16

Luescher, Michael, and Jeffrey Bode. "Evidence for a Radical Mechanism in Cu(II)-Promoted SnAP Reactions." Synlett 30, no. 04 (2019): 464–70. http://dx.doi.org/10.1055/s-0037-1611670.

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Saturated nitrogen heterocycles can be found with increasing abundance in bioactive molecules despite a limited number of methods to access these scaffolds. However, the coupling of recently introduced SnAP [tin (Sn) amine protocol] reagents with a wide range of aldehydes and ketones has proven to be a reliable, practical, and versatile one-step approach to saturated N-heterocycles. While effective, the lack of mechanistic understanding limits efforts to develop new catalytic and enantioselective variants. To distinguish between a polar or radical mechanism, we assessed Lewis and Brønsted acid

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17

Chong, Thiam Seong, Tsz Sian Chwee, Weng Kee Leong, Ming Wah Wong, and Wai Yip Fan. "Methyl abstraction kinetics of CpFe(CO)2Me using the benzyl radical clock." Journal of Organometallic Chemistry 691, no. 4 (2006): 687–92. http://dx.doi.org/10.1016/j.jorganchem.2005.10.010.

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18

Kretzschmar, Ilona, Joshua A. Levinson, and Cynthia M. Friend. "Hydroxymethylcyclopropane on Oxygen-Covered Mo(110): A Radical Clock on a Surface." Journal of the American Chemical Society 122, no. 49 (2000): 12395–96. http://dx.doi.org/10.1021/ja002769h.

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19

Fernández-Mateos, A., P. Teijón, R. Clemente, and R. González. "A Radical Clock for Reactions of Epoxy Derivatives Induced by Titanocene Chloride." Synlett 2008, no. 20 (2008): 3208–12. http://dx.doi.org/10.1055/s-0028-1087410.

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20

Mackie, Iain D., and Gino A. DiLabio. "Ring-opening radical clock reactions: many density functionals have difficulty keeping time." Organic & Biomolecular Chemistry 9, no. 9 (2011): 3158. http://dx.doi.org/10.1039/c0ob01246g.

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21

Fu, Yao, Rui-Qiong Li, Lei Liu, and Qing-Xiang Guo. "Solvent effect is not significant for the speed of a radical clock." Research on Chemical Intermediates 30, no. 3 (2004): 279–86. http://dx.doi.org/10.1163/156856704323034012.

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22

Rychnovsky, Scott D., Takeshi Hata, Angie I. Kim, and Alexandre J. Buckmelter. "Use of a Conformational Radical Clock for Evaluating Alkyllithium-Mediated Cyclization Reactions." Organic Letters 3, no. 6 (2001): 807–10. http://dx.doi.org/10.1021/ol006866r.

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23

Jäger, Christof M., Matthias Hennemann, Andrzej Mieszała, and Timothy Clark. "An ab initio and Density Functional Theory Study of Radical-Clock Reactions." Journal of Organic Chemistry 73, no. 4 (2008): 1536–45. http://dx.doi.org/10.1021/jo702421m.

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24

Kavet, Robert, and Joseph Brain. "Cryptochromes in Mammals and Birds: Clock or Magnetic Compass?" Physiology 36, no. 3 (2021): 183–94. http://dx.doi.org/10.1152/physiol.00040.2020.

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Species throughout the animal kingdom use the Earth’s magnetic field (MF) to navigate using either or both of two mechanisms. The first relies on magnetite crystals in tissue where their magnetic moments align with the MF to transduce a signal transmitted to the central nervous system. The second and the subject of this paper involves cryptochrome (CRY) proteins located in cone photoreceptors distributed across the retina, studied most extensively in birds. According to the “Radical Pair Mechanism” (RPM), blue/UV light excites CRY’s flavin cofactor (FAD) to generate radical pairs whose singlet

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25

Mathew, L., and J. Warkentin. "The cyclopropylmethyl free-radical clock. Calibration for the 30-89.degree. C range." Journal of the American Chemical Society 108, no. 25 (1986): 7981–84. http://dx.doi.org/10.1021/ja00285a016.

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26

Jäger, Christof M, Matthias Hennemann, and Timothy Clark. "The Effect of a Complexed Lithium Cation on a Norcarane-Based Radical Clock." Chemistry - A European Journal 15, no. 10 (2009): 2425–33. http://dx.doi.org/10.1002/chem.200801076.

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27

VANNI, R., S. J. GARDEN, J. T. BANKS, and K. U. INGOLD. "ChemInform Abstract: Mechanism of Hydroxylation of Alkanes by Dimethyldioxirane. A Radical- Clock Study." ChemInform 27, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199607087.

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28

Mattalia, Jean-Marc, Michel Chanon, and Charles J. M. Stirling. "A New Radical Clock for Testing the Possibility of Electron Transfer from Carbanions." Journal of Organic Chemistry 61, no. 3 (1996): 1153–54. http://dx.doi.org/10.1021/jo951132r.

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29

Mattalia, J. M., M. Chanon, and C. J. M. Stirling. "A New Radical Clock for Testing the Possibility of Electron Transfer from Carbanions." Journal of Organic Chemistry 61, no. 25 (1996): 9072. http://dx.doi.org/10.1021/jo964020o.

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30

Hitomi, Kenichi, Luciano DiTacchio, Andrew S. Arvai, et al. "Functional motifs in the (6-4) photolyase crystal structure make a comparative framework for DNA repair photolyases and clock cryptochromes." Proceedings of the National Academy of Sciences 106, no. 17 (2009): 6962–67. http://dx.doi.org/10.1073/pnas.0809180106.

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Homologous flavoproteins from the photolyase (PHR)/cryptochrome (CRY) family use the FAD cofactor in PHRs to catalyze DNA repair and in CRYs to tune the circadian clock and control development. To help address how PHR/CRY members achieve these diverse functions, we determined the crystallographic structure of Arabidopsis thaliana (6-4) PHR (UVR3), which is strikingly (>65%) similar in sequence to human circadian clock CRYs. The structure reveals a substrate-binding cavity specific for the UV-induced DNA lesion, (6-4) photoproduct, and cofactor binding sites different from those of bacterial

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31

Flemmig, Beate, Ilona Kretzschmar, Cynthia M. Friend, and Roald Hoffmann. "The Cyclopropylmethyl−3-Butenyl Rearrangement on Mo(110): A Radical Clock on a Surface?†." Journal of Physical Chemistry A 108, no. 15 (2004): 2972–81. http://dx.doi.org/10.1021/jp0369701.

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32

Herberich, Gerhard E., Tobias Carstensen, Wolfram Klein, and Martin U. Schmidt. "Reaction of 19-valence-electron sandwich complexes with alkyl halides. A radical-clock investigation." Organometallics 12, no. 4 (1993): 1439–41. http://dx.doi.org/10.1021/om00028a071.

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33

Hartshorn, Richard M., and Shane G. Telfer. "Use of a radical clock to study the photodecarboxylation of amino acidatocobalt(III) complexes †." Journal of the Chemical Society, Dalton Transactions, no. 20 (1999): 3565–71. http://dx.doi.org/10.1039/a904451e.

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34

Bernard-Henriet, C., J. Jaud, A. Baldy, J. M. Mattalia, and M. Chanon. "Crystal structure of a new precursor of radical-clock based on the norbornenyl framework." Journal of Chemical Crystallography 27, no. 8 (1997): 485–88. http://dx.doi.org/10.1007/bf02576589.

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35

Do, Quynh, David D. Lee, Andrew N. Dinh, Ryan P. Seguin, Rutan Zhang, and Libin Xu. "Development and Application of a Peroxyl Radical Clock Approach for Measuring Both Hydrogen-Atom Transfer and Peroxyl Radical Addition Rate Constants." Journal of Organic Chemistry 86, no. 1 (2020): 153–68. http://dx.doi.org/10.1021/acs.joc.0c01920.

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36

Hilmutdinova, M. Sh, L. D. Chebotar, and O. M. Larycheva. "The State of Oxidative Metabolism in the Cardiac and Skeletal Muscle Tissue in Conditions of Light Deprivation." Ukraïnsʹkij žurnal medicini, bìologìï ta sportu 5, no. 5 (2020): 319–23. http://dx.doi.org/10.26693/jmbs05.05.319.

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The article considers the features of oxidative metabolism of cardiac and skeletal muscle tissue in the changed photoperiod, under the influence of round-the-clock light deprivation in combination with the introduction of exogenous melatonin. Material and methods. The experimental study was performed on male Wistar rats. Two groups were formed for research: intact and experimental. The animals of the intact group were in standard housing and feeding conditions, without changes in light regime. The animals of the experimental group for 30 days were in conditions of round-the-clock light depriva

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37

Liu, Lei, Wes Lee, Jun Zhou, Surjo Bandyopadhyay та Osvaldo Gutierrez. "Radical-clock α-halo-esters as mechanistic probes for bisphosphine iron-catalyzed cross-coupling reactions". Tetrahedron 75, № 2 (2019): 129–36. http://dx.doi.org/10.1016/j.tet.2018.11.043.

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38

Valentine, Ann M., Marie-Helene LeTadic-Biadatti, Patrick H. Toy, Martin Newcomb, and Stephen J. Lippard. "Oxidation of Ultrafast Radical Clock Substrate Probes by the Soluble Methane Monooxygenase fromMethylococcus capsulatus(Bath)." Journal of Biological Chemistry 274, no. 16 (1999): 10771–76. http://dx.doi.org/10.1074/jbc.274.16.10771.

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39

Engel, Paul S., and Kimberly L. Lowe. "The lifetime of the 2,2-dimethylcyclopentane-1,3-diyl biradical by the cyclopropylcarbinyl radical clock method." Tetrahedron Letters 35, no. 15 (1994): 2267–70. http://dx.doi.org/10.1016/0040-4039(94)85195-6.

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40

Kincannon, William M., Nathan A. Bruender, and Vahe Bandarian. "A Radical Clock Probe Uncouples H Atom Abstraction from Thioether Cross-Link Formation by the Radical S-Adenosyl-l-methionine Enzyme SkfB." Biochemistry 57, no. 32 (2018): 4816–23. http://dx.doi.org/10.1021/acs.biochem.8b00537.

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41

Kumar, Devesh, Samuël P. de Visser, Pankaz K. Sharma, Shimrit Cohen, and Sason Shaik. "Radical Clock Substrates, Their C−H Hydroxylation Mechanism by Cytochrome P450, and Other Reactivity Patterns: What Does Theory Reveal about the Clocks' Behavior?" Journal of the American Chemical Society 126, no. 6 (2004): 1907–20. http://dx.doi.org/10.1021/ja039439s.

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42

Lusztyuk, J., B. Maillard, S. Deycard, D. A. Lindsay, and K. U. Ingold. "Kinetics of the reaction of a secondary alkyl radical with tri-n-butylgermanium hydride and calibration of a secondary alkyl radical clock reaction." Journal of Organic Chemistry 52, no. 16 (1987): 3509–14. http://dx.doi.org/10.1021/jo00392a003.

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43

Vacher, Bernard, André Samat, and Michel Chanon. "A highly efficient radical clock as a probe of the mechanism of sulfone halogenation by perhaloalkanes." Tetrahedron Letters 26, no. 42 (1985): 5129–30. http://dx.doi.org/10.1016/s0040-4039(00)98880-4.

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44

Bowry, Vincent W., and K. U. Ingold. "A radical clock investigation of microsomal cytochrome P-450 hydroxylation of hydrocarbons. Rate of oxygen rebound." Journal of the American Chemical Society 113, no. 15 (1991): 5699–707. http://dx.doi.org/10.1021/ja00015a025.

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45

Hazimeh, Hassan, Jean-Marc Mattalia, Caroline Marchi-Delapierre, Frédéric Kanoufi, Catherine Combellas, and Michel Chanon. "Structural Effects in Radical Clocks and Mechanisms of Grignard Reagent Formation: Special Effect of a Phenyl Substituent in a Radical Clock when the Crossroads of Selectivity is at a Metal/Solution Interface." European Journal of Organic Chemistry 2009, no. 17 (2009): 2775–87. http://dx.doi.org/10.1002/ejoc.200900096.

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46

Barmet, P., J. Dommen, P. F. DeCarlo, et al. "OH clock determination by proton transfer reaction mass spectrometry at an environmental chamber." Atmospheric Measurement Techniques 5, no. 3 (2012): 647–56. http://dx.doi.org/10.5194/amt-5-647-2012.

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Abstract. The hydroxyl free radical (OH) is the major oxidizing species in the lower atmosphere. Measuring the OH concentration is generally difficult and involves elaborate, expensive, custom-made experimental setups. Thus other more economical techniques, capable of determining OH concentrations at environmental chambers, would be valuable. This work is based on an indirect method of OH concentration measurement, by monitoring an appropriate OH tracer by proton transfer reaction mass spectrometry (PTR-MS). 3-pentanol, 3-pentanone and pinonaldehyde (PA) were used as OH tracers in α-pinene (AP

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47

Barmet, P., J. Dommen, P. F. DeCarlo, et al. "OH clock determination by proton transfer reaction mass spectrometry at an environmental chamber." Atmospheric Measurement Techniques Discussions 4, no. 6 (2011): 7471–98. http://dx.doi.org/10.5194/amtd-4-7471-2011.

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Abstract. The hydroxyl free radical (OH) is the major oxidizing species in the lower atmosphere. Measuring the OH concentration is generally difficult and involves elaborate, expensive, custom-made experimental setups. Thus other more economical techniques, capable of determining OH concentrations at environmental chambers, would be valuable. This work is based on an indirect method of OH concentration measurement, by monitoring an appropriate OH tracer by proton transfer reaction mass spectrometry (PTR-MS). 3-pentanol, 3-pentanone and pinonaldehyde (PA) were used as OH tracers in α-pinene (AP

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48

Pinzon-Rodriguez, Atticus, Staffan Bensch, and Rachel Muheim. "Expression patterns of cryptochrome genes in avian retina suggest involvement of Cry4 in light-dependent magnetoreception." Journal of The Royal Society Interface 15, no. 140 (2018): 20180058. http://dx.doi.org/10.1098/rsif.2018.0058.

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The light-dependent magnetic compass of birds provides orientation information about the spatial alignment of the geomagnetic field. It is proposed to be located in the avian retina, and be mediated by a light-induced, biochemical radical-pair mechanism involving cryptochromes as putative receptor molecules. At the same time, cryptochromes are known for their role in the negative feedback loop in the circadian clock. We measured gene expression of Cry1, Cry2 and Cry4 in the retina, muscle and brain of zebra finches over the circadian day to assess whether they showed any circadian rhythmicity.

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49

Liu, Katherine E., Cathy C. Johnson, Martin Newcomb, and Stephen J. Lippard. "Radical clock substrate probes and kinetic isotope effect studies of the hydroxylation of hydrocarbons by methane monooxygenase." Journal of the American Chemical Society 115, no. 3 (1993): 939–47. http://dx.doi.org/10.1021/ja00056a018.

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50

Murata, Shigeru, Yasuhiro Tsubone, Reina Kawai, Daisuke Eguchi, and Hideo Tomioka. "Mechanistic studies of intramolecular CH insertion reaction of arylnitrenes: isotope effect, configurational purity and radical clock studies." Journal of Physical Organic Chemistry 18, no. 1 (2004): 9–20. http://dx.doi.org/10.1002/poc.837.

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