Issue 10, 2005

Effects of 4,5-dimethoxy groups on the time-resolved photoconversion of 2-nitrobenzyl alcohols and 2-nitrobenzaldehyde into nitroso derivatives

Abstract

The photoinduced conversion of the aci-nitro in the nitroso form was studied with four compounds containing the o-nitrobenzyl moiety in solution at ambient temperature using time-resolved UV-vis spectroscopy. For 4,5-dimethoxy-2-nitrobenzyl alcohol (2) and 4,5-methylenedioxy-2-nitrobenzyl alcohol (3) the absorption spectra are red-shifted and, in contrast to the parent 2-nitrobenzyl alcohol (1), a triplet state with CT character was detected after the 308 nm laser pulse. The other photochemical properties of 13 are similar. The aci-nitro form of 13 in acetonitrile or ethanol is quenched by water, the rate constant is (0.3–1.7) × 105 M−1 s−1. A CT triplet state and the nitroso product but no aci-nitro form were observed for 4,5-methylenedioxy-2-nitrobenzaldehyde (4). The conversion of the aci-nitro into the nitroso monomer and eventual dimer formation were studied by FTIR spectroscopy. The common features and specific differences in the photoreaction mechanisms of 14 are discussed.

Graphical abstract: Effects of 4,5-dimethoxy groups on the time-resolved photoconversion of 2-nitrobenzyl alcohols and 2-nitrobenzaldehyde into nitroso derivatives

Article information

Article type
Paper
Submitted
06 May 2005
Accepted
10 Jun 2005
First published
11 Aug 2005

Photochem. Photobiol. Sci., 2005,4, 822-828

Effects of 4,5-dimethoxy groups on the time-resolved photoconversion of 2-nitrobenzyl alcohols and 2-nitrobenzaldehyde into nitroso derivatives

H. Görner, Photochem. Photobiol. Sci., 2005, 4, 822 DOI: 10.1039/B506393K

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