Is There Stereoselectivity in Spin Trapping Superoxide by 5-tert-Butoxycarbonyl-5-methyl-1-pyrroline N-oxide?
Ester-containing nitrones, including 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-oxide 5, have been reported to be robust spin traps for superoxide (O2•-). Using a chiral column, we have been able to isolate the two enantiomers of nitrone 5. With enantiomerically pure nitrone 5a and 5b we explored whether one of these isomers was solely responsible for the EPR spectrum of aminoxyl 6. Data obtained demonstrate that the spin trapping of O2•- by nitrone 5a and nitrone 5b afford the identical EPR spectra and lifetimes in homogenous aqueous solution and exhibit the same ratio of cis and trans isomers. Quantum chemical modeling in vacuo also finds no difference, aside from the expected optical activity, arising from the difference in stereochemistry.
- Research Organization:
- Pacific Northwest National Laboratory (PNNL), Richland, WA (US), Environmental Molecular Sciences Laboratory (EMSL)
- Sponsoring Organization:
- USDOE
- DOE Contract Number:
- AC05-76RL01830
- OSTI ID:
- 15020654
- Report Number(s):
- PNNL-SA-45026; 6894; KP1704020; TRN: US200521%%70
- Journal Information:
- Journal of Organic Chemistry, 70(18):7093-7097, Vol. 70, Issue 18
- Country of Publication:
- United States
- Language:
- English
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