Photolysis of (Halomethyl)naphthalenes: An Investigation of the Heterolysis and Homolysis of Carbon-Halogen Bonds in (Arylmethyl)halides
Slocum, Gregory Howard
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https://hdl.handle.net/2142/70239
Description
Title
Photolysis of (Halomethyl)naphthalenes: An Investigation of the Heterolysis and Homolysis of Carbon-Halogen Bonds in (Arylmethyl)halides
Author(s)
Slocum, Gregory Howard
Issue Date
1984
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Abstract
The photolysis of (halomethyl)naphthalenes in methanol and cyclohexane was examined by means of product and quantum yield studies, sensitization and quenching experiments, and the technique of transient absorption spectroscopy. Evidence is presented for three modes of heterolytic bond cleavage. The first originates from an excited singlet state, and may be direct or may involve an exciplex formed during sensitization. The second mode is through an exciplex of the (halomethyl)naphthalene and a triplet sensitizer. The third mode appears to be important only for (iodomethyl)naphthalene (19I) and involves formation of a complex between ground state 19I and atomic iodine which gives solvolysis product and diiodide radical ion on reaction with methanol. The triplet (halomethyl)naphthalenes are found to be unreactive. Carbon-halogen bond homolysis occurs apparently both from the direct photolysis and from sensitization via exciplex formation.
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