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.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
El-Gendy
Bahaa El-Dien M
Bel-D
Draghici
Bogdan
B
Hall
C Dennis
CD
Steel
Peter J
PJ
D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013777:Tetrazoles / Q000138:chemical synthesis / Q000737:chemistry*
D013777:Tetrazoles