Concept of polarity of free radicals in reactions of addition to olefins

Volovik, S. V.; Dyadyusha, G. G.; Станинец, В. И.

doi:10.1007/bf00522538

Cited by 5 publications

(3 citation statements)

References 16 publications

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“…Free radical polarity or the ability of radicals to react with polar or nonpolar agents are important factors affecting the potential biological targets of free radical attack. For example, acetonyl radicals are electrophilic in nature while benzoyl radicals are largely nucleophilic suggesting that they may have different targets within the body. , However, there is a paucity of data regarding the specific biological targets of free radicals derived from cigarette smoke or e-cigarette/HnB aerosols, in part due to the lack of information regarding the chemical nature of the radicals produced. To begin to understand the nature of radical species produced by different tobacco products, we conducted exploratory experiments to determine the interaction of these radicals with solvents of differing polarity.…”

Section: Discussionmentioning

confidence: 99%

“…While the exact structures of the e-cig radicals remain unknown, they do appear to be different as compared to conventional cigarettes . As a radical’s structure and its electrophilic or nucleophilic nature can dictate the types of molecules it may interact with, assessing basic chemical characteristics may help us identify their potential impacts in the body. , With the emergence of these new HnB products, we sought to characterize the polarity and determine the levels of free radicals generated from these devices and compare them to other tobacco products.…”

Section: Introductionmentioning

confidence: 99%

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Free Radical Production and Characterization of Heat-Not-Burn Cigarettes in Comparison to Conventional and Electronic Cigarettes

Bitzer

Goel

Trushin

et al. 2020

Chem. Res. Toxicol.

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With conventional cigarettes, the burning cone reaches temperatures of >900 °C, resulting in the production of numerous toxicants and significant levels of highly reactive free radicals. In attempts to eliminate combustion while still delivering nicotine and flavorings, a newer alternative tobacco product has emerged known as “heat-not-burn” (HnB). These products heat tobacco to temperatures of 250–350 °C depending on the device allowing for the volatilization of nicotine and flavorants while potentially limiting the production of combustion-related toxicants. To better understand how the designs of these new products compare to conventional cigarettes and different styles of electronic cigarettes (e-cigs), we measured and partially characterized their production of free radicals. Smoke or aerosols were trapped by a spin trap phenyl-N-tert-butylnitrone (PBN) and analyzed for free radicals using electron paramagnetic resonance (EPR). Free radical polarity was assessed by passing the aerosol or smoke through either a polar or nonpolar trap prior to being spin trapped with PBN. Particulate-phase radicals were detected only for conventional cigarettes. Gas-phase free radicals were detected in smoke/aerosol from all products with levels for HnB (IQOS, Glo) (12 pmol/puff) being similar to e-cigs (Juul, SREC, box mod e-cig) and hybrid devices (Ploom) (5–40 pmol/puff) but 50-fold lower than conventional cigarettes (1R6F). Gas phase radicals differed in polarity with HnB products and conventional cigarettes producing more polar radicals compared to those produced from e-cigs. Free radical production should be considered in evaluating the toxicological profile of nicotine delivery products and identification of the radicals is of paramount importance.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Free Radical Production and Characterization of Heat-Not-Burn Cigarettes in Comparison to Conventional and Electronic Cigarettes

Bitzer

Goel

Trushin

et al. 2020

Chem. Res. Toxicol.

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“…The `phility' concept, 41 first, allows one to determine the most reactive centre of a non-symmetrical alkene molecule; second, to predict changes in the reactivity of a given radical with different alkenes or a given alkene with different radicals; and third, to estimate the preferred direction of charge transfer in the system (from the alkene to the radical or, conversely, from the radical to the alkene).…”

Section: Potential Energy Surfaces Of Reactions and Structure Of Tran...mentioning

confidence: 99%

Simulation of reactions of fluoroalkenes by quantum chemistry methods

Fokin¹,

Landau²

1998

Russ. Chem. Rev.

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The indium activation diagnostic was calibrated using an accelerator neutron source to facilitate the diagnosis of deuterium-deuterium (DD) neutron yields of implosion experiments in the Shenguang-III facility. The scattered neutron background of the accelerator room was measured by placing a polypropylene shadow bar in front of the indium sample, so as to correct the calibrated factor of this activation diagnostic. The proper size of the shadow bar was given by Monte Carlo simulation. The calibration results showed that the scattered neutron background of the accelerator room was about 9% of the incident neutrons on the sample. Subtracting the portion induced by the neutron background, the calibrated factor for this sample condition was 4.52×10 -7 counts/n with an uncertainty of 4.3%.

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