Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine

The effects on the redox properties of modifying the molecular skeleton of neutral bis-2-(4-dimethylamino)pyridinylidene electron donors, derived from 4-dimethylaminopyridine (4-DMAP), have been explored, by varying two parameters: (i) the length of a polymethylene chain linking the two pyridine-der...

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Main Authors: Jean Garnier, Alan R. Kennedy, Leonard E. A. Berlouis, Andrew T. Turner, John A. Murphy
Format: Article
Language:English
Published: Beilstein-Institut 2010-07-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.6.73
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author Jean Garnier
Alan R. Kennedy
Leonard E. A. Berlouis
Andrew T. Turner
John A. Murphy
author_facet Jean Garnier
Alan R. Kennedy
Leonard E. A. Berlouis
Andrew T. Turner
John A. Murphy
author_sort Jean Garnier
collection DOAJ
description The effects on the redox properties of modifying the molecular skeleton of neutral bis-2-(4-dimethylamino)pyridinylidene electron donors, derived from 4-dimethylaminopyridine (4-DMAP), have been explored, by varying two parameters: (i) the length of a polymethylene chain linking the two pyridine-derived rings and (ii) the nature of the nitrogen substituents on the 4 and 4′ positions of the precursor pyridines. Restricting the bridge length to two methylene units significantly altered the redox profile, while changes in the nitrogen-substituents at the 4 and 4′ positions led to only slight changes in the redox potentials.
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spelling doaj.art-6c989dd911d54466b23ca6c75a23cf712022-12-21T17:25:57ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972010-07-01617310.3762/bjoc.6.731860-5397-6-73Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridineJean Garnier0Alan R. Kennedy1Leonard E. A. Berlouis2Andrew T. Turner3John A. Murphy4WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, U.K.WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, U.K.WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, U.K.PR&D Laboratory Building, AstraZeneca, Silk Road Business Park, Charterway, Macclesfield SK10 2NA, United KingdomWestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, U.K.The effects on the redox properties of modifying the molecular skeleton of neutral bis-2-(4-dimethylamino)pyridinylidene electron donors, derived from 4-dimethylaminopyridine (4-DMAP), have been explored, by varying two parameters: (i) the length of a polymethylene chain linking the two pyridine-derived rings and (ii) the nature of the nitrogen substituents on the 4 and 4′ positions of the precursor pyridines. Restricting the bridge length to two methylene units significantly altered the redox profile, while changes in the nitrogen-substituents at the 4 and 4′ positions led to only slight changes in the redox potentials.https://doi.org/10.3762/bjoc.6.73dication4-DMAPelectron donorelectron transferradical cationredoxreduction
spellingShingle Jean Garnier
Alan R. Kennedy
Leonard E. A. Berlouis
Andrew T. Turner
John A. Murphy
Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine
Beilstein Journal of Organic Chemistry
dication
4-DMAP
electron donor
electron transfer
radical cation
redox
reduction
title Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine
title_full Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine
title_fullStr Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine
title_full_unstemmed Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine
title_short Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine
title_sort structure and reactivity in neutral organic electron donors derived from 4 dimethylaminopyridine
topic dication
4-DMAP
electron donor
electron transfer
radical cation
redox
reduction
url https://doi.org/10.3762/bjoc.6.73
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