Reactivity of sydnones with singlet oxygen

Bhattacharyya, K. ; Das, P. K. ; George, M. V. (1986) Reactivity of sydnones with singlet oxygen Journal of Photochemistry, 34 (1). pp. 13-22. ISSN 0047-2670

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The rate constants kr for the reaction of several sydnones with singlet oxygen (1O2) have been measured by the competition technique based on the 485 nm laser flash photolysis of a 1O2 sensitizer and the kinetics of depletion of 1,3-diphenylisobenzofuran. The sydnone with a methyl substituent at the 4-position is particularly reactive (kr = (1 - 5) × 107 M-1 s-1 in various solvents). In contrast, the sydnones that are unsubstituted at the 4-position exhibit only poor reactivity towards 1O2 (kr ≤ 5 × 105 M-1 s-1 in methanol and benzene). The solvent polarity has a small positive influence on kr; for example, on going from carbon tetrachloride to acetone or acetonitrile, the increase in kr for 4-methyl-3-p-tolylsydnone is only twofold to threefold. This can ben explained by a slight increase in dipole moment on achieving a transition state from a sydnone substrate that is already considerably polar.

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Deposited On:10 Nov 2010 06:17
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