Structure and infrared spectrum of 2-hydroxyphenyl radical

Infrared spectrum of 2-hydroxyphenyl, C 6H 4-OH, produced from 2-iodophenol in a low-temperature argon matrix upon UV irradiation ( λ>280 nm) was measured with an FT-IR spectrophotometer. This radical was found to be less stable by 120 kJ mol −1 than phenoxyl, C 6H 5-O , by a density functional t...

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Bibliographic Details
Published in:Chemical physics letters 2004-07, Vol.392 (1), p.259-264
Main Authors: Nagata, Mitsuhiro, Futami, Yoshisuke, Akai, Nobuyuki, Kudoh, Satoshi, Nakata, Munetaka
Format: Article
Language:English
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Summary:Infrared spectrum of 2-hydroxyphenyl, C 6H 4-OH, produced from 2-iodophenol in a low-temperature argon matrix upon UV irradiation ( λ>280 nm) was measured with an FT-IR spectrophotometer. This radical was found to be less stable by 120 kJ mol −1 than phenoxyl, C 6H 5-O , by a density functional theory calculation. Two final photoproducts were identified as cyclopentadienylidenemethanone and 4-iodo-2,5-cyclohexadienone in analogy with the photoproducts of 2-chloro and 2-bromophenols. A kinetic analysis shows that the latter is produced via 2-hydroxyphenyl by hydrogen migration and iodine recombination while the former is produced by Wolff rearrangement after elimination of hydrogen iodide.
ISSN:0009-2614
1873-4448
DOI:10.1016/j.cplett.2004.04.120