The structure of N-aminoazoles: an experimental (X-ray and15N NMR) and theoretical study
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 2,p. 237-244
- https://doi.org/10.1039/p29900000237
Abstract
INDO calculations with complete optimization of the geometries (INDO ∥ INDO) have been carried out on the seventeen parent N-methyl and N-aminoazoles. The results are consistent with the available experimental evidence and provide a coherent picture of the conformation of the sp3 amino group. The nitrogen-15 chemical shifts of eleven N-aminoazoles have been determined for the first time. Experimental determination of the geometry by X-ray crystallography has been carried out on 1 -aminobenzimidazole: P21/n,a= 7.972 5(4), b= 11.041 1 (4), c= 7.525 1 (3)Å, β= 94.435(3)°, and on 2-aminobenzotriazole: P21/c, a= 11.590 0 (5), b= 4.603 1 (8), c= 12.559 1 (8)Å, β= 109.914(4)°.Keywords
This publication has 21 references indexed in Scilit:
- Effect of N‐substituents on the 13C NMR parameters of azolesMagnetic Resonance in Chemistry, 1988
- Binding of ammonium ion to azoles in the gas phase. A theoretical study of the N.cntdot.H+.cntdot.N ionic hydrogen bondThe Journal of Organic Chemistry, 1987
- 1,2,3‐Triazine, III Synthese von N‐Aminopyrazolen und deren Oxidation zu 1,2,3‐Triazinen. Molekülstruktur des 1,2,3‐TriazinsEuropean Journal of Organic Chemistry, 1985
- 1H, 13C and 15N NMR spectra of [1,2‐15N2]pyrazole derivativesMagnetic Resonance in Chemistry, 1984
- N,N-Linked biazoles. III. MNDO calculations on the conformation of N,N-linked biazoles and their quaternary saltsCanadian Journal of Chemistry, 1984
- Pyrazoles and their Benzo DerivativesPublished by Elsevier ,1984
- Enhancement of nuclear magnetic resonance signals by polarization transferJournal of the American Chemical Society, 1979
- 1,2,3-BenzotriazinesJournal of the Chemical Society, Perkin Transactions 1, 1975
- Reactive intermediates. Part I. Synthesis and oxidation of 1- and 2-aminobenzotriazoleJournal of the Chemical Society C: Organic, 1969
- Über einige neue ditertiäre Hydrazine und Tetrazene der aromatischen Reihe (XIII)European Journal of Organic Chemistry, 1912