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Photoinduced intramolecular charge shift reaction in ammonium N-(3,5-dinitrobenzoyl)-α-phenylglycinate adducts

Paper ID Volume ID Publish Year Pages File Format Full-Text
27526 44028 2010 4 PDF Available
Title
Photoinduced intramolecular charge shift reaction in ammonium N-(3,5-dinitrobenzoyl)-α-phenylglycinate adducts
Abstract

Ammonium N-(3,5-dinitrobenzoyl)-α-phenylglycinate adducts were synthesized and characterized by using different protonated amines as counter-ion: NH4+, (CH3–CH2–)2NH2+, (CH3–CH2–CH2)NH3+, (CH3–CH2–CH2–CH2–)NH3+ and (CH3–CH2–)3NH+. A photochemical process was observed under ultraviolet (λexc, 254 nm) or solar irradiation, both in solid state and in solution: DMSO, acetone or acetonitrile. 3,5-Dinitrobenzene and carboxylate groups, separated by an N-benzylamide bridge, are present in these adducts, acting as electron acceptor and electron donor, respectively. Spectroscopic analyses (NMR, IR and UV–vis) suggest a photoinduced intramolecular electron transfer. A first-order photochemical kinetics was proposed in DMSO/(n-propylammonium N-(3,5-dinitrobenzoyl)-α-phenylglycinate) solution; such behavior was similar for all adducts studied, probably due to total salt dissociation in solution. In the solid state, however, electron transfer process efficiency is directly proportional to Lewis base (amine) strength of the adduct counter-ion. Decarboxylation is observed after the irradiation process, giving rise to a σ-adduct intermediate, and subsequent formation of benzaldehyde and 3,5-dinitrobenzamide degradation products.

Keywords
Photoinduced; Electron transfer; Charge shift; N-(3,5-dinitrobenzoyl)-α-phenylglycinate; σ-Adduct
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Photoinduced intramolecular charge shift reaction in ammonium N-(3,5-dinitrobenzoyl)-α-phenylglycinate adducts
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 214, Issue 1, 5 July 2010, Pages 108–111
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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Price was $35.95
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Price after discount Only $4.95
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