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NMR study of the tautomeric behavior of N-(α-aminoalkyl)tetrazoles.

NMR study of the tautomeric behavior of N-(α-aminoalkyl)tetrazoles. N-(α-Aminoalkyl)tetrazoles exist in solution as equilibrium mixtures of N1 and N2 tautomers. The position of equilibrium depends significantly on the polarity of the solvent and the substituents in the tetrazole ring. Interconversion between individual tautomers is shown to proceed via tight ion-pair intermediates in which intramolecular recombination is faster than the intermolecular crossover since the latter probably requires solvent separation of ion-pair intermediates. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png The Journal of Organic Chemistry Pubmed

NMR study of the tautomeric behavior of N-(α-aminoalkyl)tetrazoles.

The Journal of Organic Chemistry , Volume 75 (19): -6391 – Jan 4, 2011

NMR study of the tautomeric behavior of N-(α-aminoalkyl)tetrazoles.


Abstract

N-(α-Aminoalkyl)tetrazoles exist in solution as equilibrium mixtures of N1 and N2 tautomers. The position of equilibrium depends significantly on the polarity of the solvent and the substituents in the tetrazole ring. Interconversion between individual tautomers is shown to proceed via tight ion-pair intermediates in which intramolecular recombination is faster than the intermolecular crossover since the latter probably requires solvent separation of ion-pair intermediates.

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ISSN
0022-3263
DOI
10.1021/jo101195z
pmid
20828118

Abstract

N-(α-Aminoalkyl)tetrazoles exist in solution as equilibrium mixtures of N1 and N2 tautomers. The position of equilibrium depends significantly on the polarity of the solvent and the substituents in the tetrazole ring. Interconversion between individual tautomers is shown to proceed via tight ion-pair intermediates in which intramolecular recombination is faster than the intermolecular crossover since the latter probably requires solvent separation of ion-pair intermediates.

Journal

The Journal of Organic ChemistryPubmed

Published: Jan 4, 2011

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