Photochemistry and Reactivity of the Phenyl Radical–Water System: A Matrix Isolation and Computational Study

Mardyukov, Artur; Crespo‐Otero, Rachel; Sánchez-García, Elsa; Sander, Wolfram

doi:10.1002/chem.200903362

Cited by 33 publications

(32 citation statements)

References 66 publications

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“…48 The abstraction of hydrogen from benzene by OH radicals forming phenyl radicals is regarded as a minor process. 49 Even if the ionization of benzene followed by the deprotonation in aprotic solvents forms phenyl radicals, it abstracts hydrogen from water, forming OH radicals and benzene, and thus 1 is expected. 49 The successive reactions of 1 forming phenol and biphenyl have been well investigated under various conditions.…”

Section: ¹1mentioning

confidence: 99%

“…49 Even if the ionization of benzene followed by the deprotonation in aprotic solvents forms phenyl radicals, it abstracts hydrogen from water, forming OH radicals and benzene, and thus 1 is expected. 49 The successive reactions of 1 forming phenol and biphenyl have been well investigated under various conditions. The dimerization of 1 yields biphenyl after the dehydration.…”

Section: ¹1mentioning

confidence: 99%

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Synthesis of Hydrophilic and Hydrophobic Carbon Nanoparticles from Benzene/Water Bilayer Solution with Femtosecond Laser Generated Plasma Filaments in Water

Hamaguchi¹,

Okamoto²,

Mitamura³

et al. 2014

Bulletin of the Chemical Society of Japan

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We synthesized hydrophilic and hydrophobic carbon nanoparticles (CNPs) by femtosecond laser (0.8¯m, 40 fs) irradiation of the water layer of an aerated benzene/water (B/W) bilayer solution. Focusing intense femtosecond laser pulses onto water creates a high density of reactive species such as hydroxyl radicals in a well-confined volume; i.e., plasma filament. The properties of the particle surface were controlled simply by adjusting the laser focusing position, the duration between the preparation of B/W bilayer solution and the laser irradiation. The hydrophobic CNPs appeared to be nearly identical in size and morphology to hydrophilic CNPs. Raman spectroscopy revealed that both particles had a graphitic and disordered structure; however, IR spectroscopy clearly showed that the hydroxy group is the origin of the hydrophilicity. The time evolution of particle formation, products in water, and benzene dissolution behavior in water reveals that the surface properties are determined by the concentration of benzene in water. The diluted aqueous benzene solution gave hydrophilic particles; however, the density of particles was much smaller than that formed in B/W bilayer solution. We concluded that the production of denser hydrophilic CNPs in B/W bilayer was achieved by limiting the concentration of benzene in water layer by B/W interface, and by continuously supplying benzene into water layer through B/W interface. We discuss the subsequent reaction mechanism leading to CNPs of different surface characters.

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Section: ¹1mentioning

confidence: 99%

Section: ¹1mentioning

confidence: 99%

Synthesis of Hydrophilic and Hydrophobic Carbon Nanoparticles from Benzene/Water Bilayer Solution with Femtosecond Laser Generated Plasma Filaments in Water

Hamaguchi¹,

Okamoto²,

Mitamura³

et al. 2014

Bulletin of the Chemical Society of Japan

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“…60 The primary thermal product of the reaction between phenyl radical and water is a weakly bound complex stabilized by an OH Á Á Á p interaction. This complex is photolabile, and visible light irradiation (lW 420 nm) resulted in hydrogen atom transfer from water to the phenyl radical and the formation of a highly labile complex between benzene and the OH radical.…”

Section: Fragmentation Reactions and Formation Of Complexes Or Weaklymentioning

confidence: 99%

“…59Fig. 24Reaction of phenyl radical with water and subsequent photochemical reaction of the formed species 60. …”

mentioning

confidence: 99%

Light induced reactions in cryogenic matrices

Fausto

Gómez‐Zavaglia

2011

Photochemistry

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“…[4] Most recently, the role of unpaired electrons in the interactions of aromatic radicals with water was also investigated by us, evidencing the effect of the aromatic ring on complex formation in radicals. [5][6][7] The nitric oxide (NO) molecule is a radical involved in many biological processes. [8][9][10][11] Despite its small size, the theoretical study of NO associations with other molecules remains a challenge due to the radical character of the NO monomer and the van der Waals (vdW) character of its complexes.…”

Section: Introductionmentioning

confidence: 99%

Complexes of nitric oxide with water and imidazole

et al. 2015

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NO-Imi-H 2 O complexes can be used as a model to investigate the interactions of histidine with nitric oxide and water in biological systems like myoglobin. We discuss here the water-imidazole, water-nitric oxide dimers and the trimolecular complexes of nitric oxide with water and imidazole from the donor-acceptor point of view using the Natural Bond Orbitals (NBO) and Energy Decomposition Analysis (EDA) schemes. The comparison between trimolecular and bimolecular complexes shows that in general, the stabilization energies are more sensitive to changes in the interactions of imidazole with water than to changes in the interactions with nitric oxide. The effect of imidazole ring protonation on the geometry and stabilization of the complexes is also investigated. We found that cooperative effects are more relevant in charged complexes and planar structures than in neutral species and non-planar complexes. The driving forces governing the interactions between open and closed shell systems are also discussed with special emphasis on the role of lone pairs and unpaired electrons.

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Photochemistry and Reactivity of the Phenyl Radical–Water System: A Matrix Isolation and Computational Study

Cited by 33 publications

References 66 publications

Synthesis of Hydrophilic and Hydrophobic Carbon Nanoparticles from Benzene/Water Bilayer Solution with Femtosecond Laser Generated Plasma Filaments in Water

Synthesis of Hydrophilic and Hydrophobic Carbon Nanoparticles from Benzene/Water Bilayer Solution with Femtosecond Laser Generated Plasma Filaments in Water

Light induced reactions in cryogenic matrices

Complexes of nitric oxide with water and imidazole

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