Controlled Photochemical Release of Nitric Oxide from O 2-Benzyl-Substituted Diazeniumdiolates

An investigation of potential photosensitive protecting groups for diazeniumdiolates (R2NN(O)NO-) has been initiated, and here the effect of meta electron-donating groups on the photochemistry of O 2-benzyl-substituted diazeniumdiolates (R2NN(O)NOCH2Ar) is reported. Photolysis of the parent benz...

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Published inJournal of the American Chemical Society Vol. 124; no. 33; pp. 9806 - 9811
Main Authors Ruane, Patrick H, Bushan, K. Mani, Pavlos, Christopher M, D'S, Raechelle A, Toscano, John P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.08.2002
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
NUCLEOPHILES
COMPLEX-IONS
NO
CONTROLLED BIOLOGICAL RELEASE
ORGANIC-PHOTOCHEMISTRY
CURRENT TRENDS
DESIGN
CHEMISTRY
DONORS
PHOTOLYSIS
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Abstract An investigation of potential photosensitive protecting groups for diazeniumdiolates (R2NN(O)NO-) has been initiated, and here the effect of meta electron-donating groups on the photochemistry of O 2-benzyl-substituted diazeniumdiolates (R2NN(O)NOCH2Ar) is reported. Photolysis of the parent benzyl derivative (Ar = Ph) results almost exclusively in undesired photochemistrythe formation of nitrosamine and an oxynitrene intermediate with very little, if any, photorelease of the diazeniumdiolate. We have been able to use meta substitution to tune the photochemistry of these benzylic systems. The desired diazeniumdiolate photorelease has been shown to become more substantial with stronger π-donating meta substituents. This effect has been verified by direct observation of the photoreleased diazeniumdiolate with 1H NMR spectroscopy and by NO quantification measurements conducted in high- and low-pH solutions. In addition, the observed rates of NO release are consistent with that expected for normal thermal decomposition of the diazeniumdiolate in aqueous solutions and also show the same pH dependence.
AbstractList An investigation of potential photosensitive protecting groups for diazeniumdiolates (R2N-N(O)=NO-) has been initiated, and here the effect of meta electron-donating groups on the photochemistry of O-2-benzyl-substituted diazeniumdiolates (R2N-N(O)=NOCH2Ar) is reported. Photolysis of the parent benzyl derivative (Ar = Ph) results almost exclusively in undesired photochemistry-the formation of nitrosamine and an oxynitrene intermediate with very little, if any, photorelease of the diazeniumdiolate. We have been able to use meta substitution to tune the photochemistry of these benzylic systems. The desired diazeniumdiolate photorelease has been shown to become more substantial with stronger pi-donating meta substituents. This effect has been verified by direct observation of the photoreleased diazeniumdiolate with H-1 NIMR spectroscopy and by NO quantification measurements conducted in high- and low-pH solutions. In addition, the observed rates of NO release are consistent with that expected for normal thermal decomposition of the diazeniumdiolate in aqueous solutions and also show the same pH dependence.
An investigation of potential photosensitive protecting groups for diazeniumdiolates (R2NN(O)NO-) has been initiated, and here the effect of meta electron-donating groups on the photochemistry of O 2-benzyl-substituted diazeniumdiolates (R2NN(O)NOCH2Ar) is reported. Photolysis of the parent benzyl derivative (Ar = Ph) results almost exclusively in undesired photochemistrythe formation of nitrosamine and an oxynitrene intermediate with very little, if any, photorelease of the diazeniumdiolate. We have been able to use meta substitution to tune the photochemistry of these benzylic systems. The desired diazeniumdiolate photorelease has been shown to become more substantial with stronger π-donating meta substituents. This effect has been verified by direct observation of the photoreleased diazeniumdiolate with 1H NMR spectroscopy and by NO quantification measurements conducted in high- and low-pH solutions. In addition, the observed rates of NO release are consistent with that expected for normal thermal decomposition of the diazeniumdiolate in aqueous solutions and also show the same pH dependence.
Author Ruane, Patrick H
Pavlos, Christopher M
D'S, Raechelle A
Bushan, K. Mani
Toscano, John P
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Issue 33
Keywords NUCLEOPHILES
COMPLEX-IONS
NO
CONTROLLED BIOLOGICAL RELEASE
ORGANIC-PHOTOCHEMISTRY
CURRENT TRENDS
DESIGN
CHEMISTRY
DONORS
PHOTOLYSIS
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Snippet An investigation of potential photosensitive protecting groups for diazeniumdiolates (R2NN(O)NO-) has been initiated, and here the effect of meta...
An investigation of potential photosensitive protecting groups for diazeniumdiolates (R2N-N(O)=NO-) has been initiated, and here the effect of meta...
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SubjectTerms Chemistry
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Title Controlled Photochemical Release of Nitric Oxide from O 2-Benzyl-Substituted Diazeniumdiolates
URI http://dx.doi.org/10.1021/ja026900s
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