Spectroscopic detection of two neutral CHNO2 isomers: nitrocarbene and nitrosoformaldehyde

O'bannon, P. E.; Suelzle, Detlev; Dailey, William P.; Schwarz, Helmut

doi:10.1021/ja00027a045

Cited by 20 publications

(15 citation statements)

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“…Yet, the NMR spectra indicates that both cis and trans conformations exist when they are in solution in a ratio of ca. 10:1, in agreement with the literature reports …”

Section: Experimental Sectionsupporting

confidence: 93%

Photocalibrated NO Release from N-Nitrosated Napthalimides upon One-Photon or Two-Photon Irradiation

Zhang¹,

Wu²,

Shang³

et al. 2016

Anal. Chem.

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NO donors are routinely used as the exogenous source in in vitro studies. However, the kinetics or the dose of NO release from the existing donors is not readily monitored. This complicates the elucidation of the involvement of NO in a biological response. We report herein a series of NO donors (NOD545a-g), whose NO release is triggered by UV light at 365 nm or a two-photon laser at 740 nm, and importantly, their NO release is accompanied by a drastic fluorescence turn-on, which has been harnessed to follow the kinetics and dose of NO release in a real-time fashion with spectroscopic methods or microscopic methods in in vitro studies. These merits have rendered NOD545a-g useful molecular tools in NO biology.

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“…Yet, the NMR spectra indicates that both cis and trans conformations exist when they are in solution in a ratio of ca. 10:1, in agreement with the literature reports …”

Section: Experimental Sectionsupporting

confidence: 93%

Photocalibrated NO Release from N-Nitrosated Napthalimides upon One-Photon or Two-Photon Irradiation

Zhang¹,

Wu²,

Shang³

et al. 2016

Anal. Chem.

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“…The direct spectroscopic observation of acyl nitroso compounds has been accomplished in the gas phase using both charge reversal and neutralization-reionization mass spectrometry [120,121] and more recently in solution using nanosecond timeresolved IR spectroscopy [122].…”

Section: The Intermediacy Of Acyl Nitroso Species In Reactionsmentioning

confidence: 99%

Donors of HNO

Miranda

Nagasawa

Toscano

2005

CTMC

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Recent comparisons of the pharmacological effects of nitric oxide (NO) and nitroxyl (HNO) donors have demonstrated that the responses to these redox-related nitrogen oxides are nearly universally dissimilar. These analyses have suggested the existence of mutually exclusive signaling pathways as a result of discrete chemical interactions of HNO and NO with a variety of critical biomolecules. Although the mechanisms of action are currently unresolved, the pharmacological responses to HNO are promising for clinical treatment of cardiovascular diseases such as heart failure, myocardial infarction and stroke. This review provides a detailed discussion of the most commonly utilized donors of HNO as well as a guideline for the characterization of novel donors.

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“…The chemistry of these species is an intriging and exciting area, which is actively investigated because of the wide biological implications [69]. Nitrosocarbonyls are fleeting intermediates and the only spectroscopic evidence for them has been provided in the gas-phase by Schwarz and co-workers using mass spectrometry techniques [73]. Nitrosocarbonyls are fleeting intermediates and the only spectroscopic evidence for them has been provided in the gas-phase by Schwarz and co-workers using mass spectrometry techniques [73].…”

Section: Detection Of Acyl Nitroso Intermediatesmentioning

confidence: 99%

Synthesis and Synthetic Applications of 1,2,4-Oxadiazole-4-Oxides

Quadrelli¹,

Caramella

2007

COC

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The first 1,2,4-oxadiazole-4-oxide was prepared by Wieland a century ago, but this compound remained largely a chemical curiosity until very recently. 1,2,4-Oxadiazole-4-oxides are a family of heterocycles closely related to the chemistry of nitrile oxides which were actively studied in the past half century and provided the basic knowledge on 1,2,4-oxadiazole-4-oxides. The dimerizations of nitrile oxides under acidic or basic conditions were thoroughly studied by different research groups, and offer the more common entries to the symmetrical substituted 1,2,4-oxadiazole-4-oxides. A more general route to symmetrical and unsymmetrical substituted 1,2,4-oxadiazole-4-oxides is based on the nitrile oxide cycloadditions to amidoximes. A variety of other 1,2,4-oxadiazole-4-oxides forming reactions are also known in the literature. Many of these reactions were neither fully exploited nor mechanistically understood since they require unusual starting reagents, often difficult to prepare, or take place affording complex mixtures of products. Some of these methods still await for improved procedures and proper mechanistic attention to be of general use and will be reviewed shortly.The chemistry of 1,2,4-oxadiazole-4-oxides is related to the fragility of the heterocyclic ring, which undergoes thermal or photochemical cycloreversion to nitriles and nitrosocarbonyl intermediates. Trapping of the nitrosocarbonyls takes place easily with dienes and enes, affording a variety of hetero Diels-Alder and ene adducts, which attract great interest because of their useful synthetic elaboration toward many natural products of potential pharmaceutical applications.The high efficiency of the photochemical cleavage of 1,2,4-oxadiazole-4-oxides at room temperature or well below affords the softest entry to the nitrosocarbonyls and allows for the study of their chemistry under convenient and simple experimental conditions. The photochemical cleavage have been applied successfully to Solid Phase chemistry, allowing for a safe and environmental friendly methodology for the synthesis of important intermediates.This report is comprehensive of the synthesis and synthetic applications of the 1,2,4-oxadiazole-4-oxides. R R' O 1 2 3 960 Quadrelli and Caramella 12 + 11 10 9 + 4 5 6 8 7 -HX 16 a N=O 13 b NH 2 _ X 9 N=O 7 NH 2

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Spectroscopic detection of two neutral CHNO2 isomers: nitrocarbene and nitrosoformaldehyde

Cited by 20 publications

References 0 publications

Photocalibrated NO Release from N-Nitrosated Napthalimides upon One-Photon or Two-Photon Irradiation

Photocalibrated NO Release from N-Nitrosated Napthalimides upon One-Photon or Two-Photon Irradiation

Donors of HNO

Synthesis and Synthetic Applications of 1,2,4-Oxadiazole-4-Oxides

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