Oxidation Reactions Using Urea-Hydrogen Peroxide; A Safe Alternative to Anhydrous Hydrogen Peroxide

Cooper, Mark S.; Heaney, H.; Newbold, Amanda J.; Sanderson, William R.

doi:10.1055/s-1990-21156

Cited by 222 publications

(124 citation statements)

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“…For 1-3, the harmonic vibrational frequencies 1 , 2 , 3 , 5 , 7 , and 8 corresponded clearly to the HP monomer vibrational modes. Moreover, 4 , 6 , and 9 were assigned as the intermolecular modes ͑see Table IV͒.…”

Section: Vibrational-frequency Analysismentioning

confidence: 91%

Basis set superposition error-counterpoise corrected potential energy surfaces. Application to hydrogen peroxide⋯X (X=F−, Cl−, Br−, Li+, Na+) complexes

Daza¹,

Dobado²,

Molina³

et al. 1999

The Journal of Chemical Physics

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Mo ր ller-Plesset ͑MP2͒ and Becke-3-Lee-Yang-Parr ͑B3LYP͒ calculations have been used to compare the geometrical parameters, hydrogen-bonding properties, vibrational frequencies and relative energies for several X Ϫ and X ϩ hydrogen peroxide complexes. The geometries and interaction energies were corrected for the basis set superposition error ͑BSSE͒ in all the complexes ͑1-5͒, using the full counterpoise method, yielding small BSSE values for the 6-311 ϩG(3d f ,2p) basis set used. The interaction energies calculated ranged from medium to strong hydrogen-bonding systems ͑1-3͒ and strong electrostatic interactions ͑4 and 5͒. The molecular interactions have been characterized using the atoms in molecules theory ͑AIM͒, and by the analysis of the vibrational frequencies. The minima on the BSSE-counterpoise corrected potential-energy surface ͑PES͒ have been determined as described by S. Simón, M. Duran, and J. J. Dannenberg, and the results were compared with the uncorrected PES.

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Section: Vibrational-frequency Analysismentioning

confidence: 91%

Basis set superposition error-counterpoise corrected potential energy surfaces. Application to hydrogen peroxide⋯X (X=F−, Cl−, Br−, Li+, Na+) complexes

Daza¹,

Dobado²,

Molina³

et al. 1999

The Journal of Chemical Physics

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“…3 Also, HP is a byproduct of several metabolic pathways, giving significant quantities of HP detectable in the human blood. 4 HP generates highly reactive radicals by different mechanisms such as the Fenton reaction, the Haber-Weiss reaction, or reactions with ascorbic acid.…”

Section: Introductionmentioning

confidence: 99%

Adenine−Hydrogen Peroxide System: DFT and MP2 Investigation

Dobado

Molina

1999

J. Phys. Chem. A

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Theoretical calculations have been performed for different possible hydrogen bonding complexes between adenine and hydrogen peroxide (AHP). The studied complexes (1-6) were cyclic ones showing two hydrogen bonds of different strength. All of the structures have been characterized at the B3LYP/6-31G(2d,p) and MP2(full)/6-31G(2d,p) levels, yielding only real frequencies (minima) at the B3LYP/6-31G(2d,p). The binding energies have been carried out for all of the structures, taking into account the so-called BSSE and yielding for the most stable structure 6 values of -11.53 and -11.95 kcal/mol at the B3LYP and MP2 levels, respectively. BSSE-free PES calculations were also performed for several complexes. The Bader analyses were also applied to investigate the hydrogen bonding electronic properties.

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“…Saponification of 20, followed by ketal hydrolysis under acidic conditions, yielded carboxylic acid 12. Cyclization of this intermediate with boron trifluoride etherate (BF 3 • OEt 2 ) afforded 2,7-dioxabicyclo[3.2.1]octan-3-one 11, which underwent Baeyer-Villiger oxidation with trifluoroperacetic acid to give analog 8 containing the dioxabicyclic fragment found in the rearranged spongian diterpene aplyviolene (5) (35).…”

Section: Synthesis Of Analogs Having the 27-dioxabicyclo[321]octanmentioning

confidence: 99%

Golgi-modifying properties of macfarlandin E and the synthesis and evaluation of its 2,7-dioxabicyclo[3.2.1]octan-3-one core

Schnermann

Beaudry

Egorova

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

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Golgi-modifying properties of the spongian diterpene macfarlandin E (MacE) and a synthetic analog, t-Bu-MacE, containing its 2,7-dioxabicyclo[3.2.1]octan-3-one moiety are reported. Natural product screening efforts identified MacE as inducing a novel morphological change in Golgi structure defined by ribbon fragmentation with maintenance of the resulting Golgi fragments in the pericentriolar region. t-Bu-MacE, which possesses the substituted 2,7-dioxabicyclo[3.2.1]octan-3-one but contains a tert-butyl group in place of the hydroazulene subunit of MacE, was prepared by chemical synthesis. Examination of the Golgi-modifying properties of MacE, t-Bu-MacE, and several related structures revealed that the entire oxygen-rich bridged-bicyclic fragment is required for induction of this unique Golgi organization phenotype. Further characterization of MacE-induced Golgi modification showed that protein secretion is inhibited, with no effect on the actin or microtubule cytoskeleton being observed. The conversion of t-Bu-MacE and a structurally related des-acetoxy congener to substituted pyrroles in the presence of primary amines in protic solvent at ambient temperatures suggests that covalent modification might be involved in the Golgi-altering activity of MacE.organelle organization | chemical biology | natural product | reactivity

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Oxidation Reactions Using Urea-Hydrogen Peroxide; A Safe Alternative to Anhydrous Hydrogen Peroxide

Cited by 222 publications

References 0 publications

Basis set superposition error-counterpoise corrected potential energy surfaces. Application to hydrogen peroxide⋯X (X=F−, Cl−, Br−, Li+, Na+) complexes

Basis set superposition error-counterpoise corrected potential energy surfaces. Application to hydrogen peroxide⋯X (X=F−, Cl−, Br−, Li+, Na+) complexes

Adenine−Hydrogen Peroxide System: DFT and MP2 Investigation

Golgi-modifying properties of macfarlandin E and the synthesis and evaluation of its 2,7-dioxabicyclo[3.2.1]octan-3-one core

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