Journal
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES
Volume 2, Issue 7, Pages 796-800Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b301818k
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In this paper we report the deprotonation yields, the pK(a), and decay kinetics of the aci-nitro intermediates of some substituted 2-nitrobenzaldehydes that can be used as photoactivatable caged proton compounds. The decay of the aci-nitro absorbance for 2-nitrobenzaldehyde occurs within a few nanoseconds from photoexcitation. Addition of electron donating methoxy substituents at positions 4 and 5 leads to lower deprotonation yields, higher pK(a), and slower decays of the aci-nitro intermediates. On the contrary, the decay rate is accelerated by the introduction of an electron-withdrawing Cl atom at position 4 in the phenyl ring, with little influence on the deprotonation yield and pK(a) of the aci-nitro intermediate.
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