Proceedings of the Eighth Conference on Time-Resolved Vibrational SpectroscopyView this Special Issue
Hiroaki Takahashi, Yoshiki Watanabe, Makoto Sakai, Masanori Tachikawa, "Photoinduced Intramolecular Hydrogen Transfer Reaction of Ortho Nitrobenzyl Compounds", Laser Chemistry, vol. 19, Article ID 029456, 6 pages, 1999. https://doi.org/10.1155/1999/29456
Photoinduced Intramolecular Hydrogen Transfer Reaction of Ortho Nitrobenzyl Compounds
Time-resolved resonance Raman and absorption spectra have revealed that the photoinduced intramolecular hydrogen transfer reaction of ortho nitrobenzyl compounds is initiated by the abstraction of methylene hydrogen by the ortho nitro group to generate the ortho aci-nitro acid isomer. In polar solvents the ortho aci-nitro acid is dissociated into the aci-nitro anion and a proton, and the proton is captured by other hydrogen accepting sites, such as 2-pyridyl, 4-pyridyl and 4-nitro groups to generate the ortho N—H quinoid, para N—H quinoid and para aci-nitro acid isomers, respectively. For 2-nitroethylbenzene and 2- and 4-(2′-nitrobenzyl)pyridines the structure of the aci-nitro anion is very similar to that of their respective ortho aci-nitro acid, while for 2,4-dinitroethylbenzene the structure of the aci-nitro anion quite resembles that of the para aci-nitro acid.
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