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Photochemistry of N-alkylsuccinimide in methanol and ethanol: An experimental and calculated investigation

Paper ID Volume ID Publish Year Pages File Format Full-Text
28251 44066 2007 7 PDF Available
Title
Photochemistry of N-alkylsuccinimide in methanol and ethanol: An experimental and calculated investigation
Abstract

The photochemistry of N-R-succinimide (R = H, Me, Et) in methanol and ethanol was investigated. Two kinds of photo-reduction products, i.e. 5-alkoxy-N-R-2-pyrrolidinone (2) and 5-(1-hydroxyalkyl)-5-alkoxy-N-R-2-pyrrolidinone (3) (alkoxy: MeO and EtO, R: Me and Et) have been identified. The formation of 2 relates to a continuous two-step H-abstraction, which is rare in the photolysis of common ketones. However, in the case of succinimide, a new pinacolic product, 5,5′-dihydroxy-5,5′-bis(2-pyrrolidinone) (4), was found for the first time. DFT calculations have been carried out in order to study the aggregation behaviors of succinimide during the photochemical process. The strong tendency to form succinimide dimer (1c–1c) via reciprocal intermolecular hydrogen-bonds is in good explanation for the generation of product 4.

Keywords
Photolysis; Succinimide; DFT; Dimer; Monomer
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Photochemistry of N-alkylsuccinimide in methanol and ethanol: An experimental and calculated investigation
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 187, Issues 2–3, 15 April 2007, Pages 377–383
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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