Laser Flash Photolysis of Dithio-2,2′-dipyridine; Structure and Reactivity of Pyridyl-2-thio Radical

Maksudul M. Alam, Akira Watanabe, Osamu Ito

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48 Citations (Scopus)

Abstract

Photochemical reactions of dithio-2,2′-dipyridine were studied by the laser flash photolysis method to clarify the structure and reactivities of the intermediate radical. The transient absorption band appearing at 490 nm was attributed to a radical in which the unpaired electron was mainly localized at the sulfur atom, namely, pyridyl-2-thio radical (2-PyS·). The low reactivities of 2-PyS· to O2 and hydrogen-atom donors were confirmed by the invariance of the decay rates of 2-PyS·. The high reactivity of 2-PyS· in addition reactions to conjugated dienes was confirmed by the accelerated first-order decay rate of 2-PyS· upon addition of the diene. For example, the addition reaction rate constant for isoprene was 1.2 × 109 M-1 s-1 (in THF), which is higher than that of PhS. Such reactivities were interpreted by comparison with MO calculations.

Original languageEnglish
Pages (from-to)3440-3444
Number of pages5
JournalJournal of Organic Chemistry
Volume60
Issue number11
DOIs
Publication statusPublished - 1995 Jun 1

ASJC Scopus subject areas

  • Organic Chemistry

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