Introduction:  Nitric Oxide Chemistry

Richter‐Addo, George B.; Legzdins, Peter; Burstyn, Judith N.

doi:10.1021/cr010188k

Cited by 165 publications

(122 citation statements)

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“…À ]-A C H T U N G T R E N N U N G (CH 2 ) 2 NH 2 + R, where R = CH 3 (1), (CH 2 ) 3 CH 3 (2), (CH 2 ) 5 CH 3 (3), and (CH 2 ) 7 CH 3 (4) were synthesized by reaction of the corresponding diamines with nitric oxide. Spectrophotometrically determined pK a (O) values, attributed to protonation at the terminal oxygen of the diazeniumdiolate group, show shifts to higher values in dependence of the chain lengths of R. The pH dependence of the decomposition of NO donors 1-3 was studied in buffered solution between pH 5 and 8 at 22 8C, from which pK a (N) values for protonation at the amino nitrogen, leading to release of NO, were estimated.…”

Section: Zwitterionic Diazeniumdiolates Of the Form Rn[n(o)nomentioning

confidence: 99%

“…[1][2][3][4] Since nitric oxide has been shown to mediate a variety of physiological and pathophysiological processes in living organisms, [5,6] the effect of NO-releasing compounds on biological systems has been studied extensively both in vitro and in vivo. [7][8][9] With regard to useful applications of NO-donating compounds as (pro)drugs, the release of nitric oxide should not occur spontaneously.…”

Section: Introductionmentioning

confidence: 99%

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Hydrophobic N‐Diazeniumdiolates and the Aqueous Interface of Sodium Dodecyl Sulfate (SDS) Micelles

et al. 2008

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Zwitterionic diazeniumdiolates of the form RN[N(O)NO(-)](CH(2))(2)NH(2) (+)R, where R=CH(3) (1), (CH(2))(3)CH(3) (2), (CH(2))(5)CH(3) (3), and (CH(2))(7)CH(3) (4) were synthesized by reaction of the corresponding diamines with nitric oxide. Spectrophotometrically determined pK(a)(O) values, attributed to protonation at the terminal oxygen of the diazeniumdiolate group, show shifts to higher values in dependence of the chain lengths of R. The pH dependence of the decomposition of NO donors 1-3 was studied in buffered solution between pH 5 and 8 at 22 degrees C, from which pK(a)(N) values for protonation at the amino nitrogen, leading to release of NO, were estimated. It is shown that the decomposition of these diazeniumdiolates is markedly catalyzed by anionic SDS micelles. First-order rate constants for the decay of 1-4 were determined in phosphate buffer pH 7.4 at 22 degrees C as a function of SDS concentration. Micellar binding constants, K(SM), for the association of diazeniumdiolates 1-3 with the SDS micelles were also determined, again showing a significant increase with increasing length of the alkyl side chains. The decomposition of 1-3 in micellar solution is quantitatively described by using the pseudo-phase ion-exchange (PIE) model, in which the degree of micellar catalysis is taken into account through the ratio of the second-order rate constants (k(2m)/k(2w)) for decay in the micelles and in the bulk aqueous phase. The decay kinetics of 1-3 were further studied in the presence of cosolvents and nonionic surfactants, but no effect on the rate of NO release was observed. The kinetic data are discussed in terms of association to the micelle-aqueous phase interface of the negatively charged micelles. The apparent interfacial pH value of SDS micelles was evaluated from comparison of the pH dependence of the first-order decay rate constants of 2 and 3 in neat buffer and the rate data obtained for the surfactant-mediated decay. For a bulk phase of pH 7.4, an interfacial pH of 5.7-5.8 was determined, consistent with the distribution of H(+) in the vicinity of the negatively charged micelles. The data demonstrate the utility of 2 and 3 as probes for the determination of the apparent pH value in the Stern region of anionic micelles.

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Section: Zwitterionic Diazeniumdiolates Of the Form Rn[n(o)nomentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Hydrophobic N‐Diazeniumdiolates and the Aqueous Interface of Sodium Dodecyl Sulfate (SDS) Micelles

et al. 2008

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“…[1][2][3][4] Initial theoretical studies of the coordination of NO to U III complexes suggested that distinct reaction pathways with NO are accessible to uranium and the early actinides, based on their oxophilicity and low-reduction potentials. 5 In light of both long-standing and recent evidence that uranium can be an efficient catalyst for important small molecule reactions, such as N 2 , CO 2 , and H 2 O reduction, [6][7][8][9][10][11][12] the potential complementary reactivity of uranium with NO may offer unique solutions for NO reduction.…”

mentioning

confidence: 99%

Reductive disproportionation of nitric oxide mediated by low-valent uranium

et al. 2016

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“…[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. Thus, weak complexes between NO and inert gases are frequently used as models to understand vdW interactions.…”

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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Introduction: Nitric Oxide Chemistry

Cited by 165 publications

References 0 publications

Hydrophobic N‐Diazeniumdiolates and the Aqueous Interface of Sodium Dodecyl Sulfate (SDS) Micelles

Hydrophobic N‐Diazeniumdiolates and the Aqueous Interface of Sodium Dodecyl Sulfate (SDS) Micelles

Reductive disproportionation of nitric oxide mediated by low-valent uranium

Complexes of nitric oxide with water and imidazole

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