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Structural study of (±) ethyl 3-acyloxy-1-azabicyclo[2.2.2]octane-3-carboxylates by 1H, 13C NMR spectroscopy, X-ray crystallography and DFT calculations

✍ Scribed by M.S. Arias-Pérez; A. Cosme; E. Gálvez; A. Morreale; J. Sanz-Aparicio; I. Fonseca

Publisher
Elsevier Science
Year
2006
Tongue
English
Weight
212 KB
Volume
789
Category
Article
ISSN
0022-2860

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✦ Synopsis

1 H, 13 C NMR spectroscopy and DFT/B3LYP calculations were applied to investigate the conformational preferences of the ethoxycarbonyl and acyloxy groups of some a-acyloxyesters derived from (G) ethyl 3-hydroxy-1-azabicyclo[2.2.2]octane-3-carboxylate. The crystal structure of (G) ethyl 3-diphenylacetoxy-1-azabicyclo[2.2.2]octane-3-carboxylate was determined by X-ray diffraction. To correlate between calculated conformations and the structure in solution, NMR chemical shifts calculations were also performed using the GIAO approach. It has been found that the lowest energetic conformer computed gives the greatest correspondance with experimental solution and solid state data.

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Structural characterization of (±)-3-ary
Structural characterization of (±)-3-aryl-1-azabicyclo[2.2.2]octan-3-ols by two-dimensional NMR spectroscopy and X-Ray crystallography. I
✍ M. S. Arias-Pérez; A. Cosme; E. Gálvez; F. Florencio; I. Fonseca; J. Sanz 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 English ⚖ 671 KB

## Abstract A series of (±)‐3‐aryl‐1‐azabicyclo[2.2.2]octan‐3‐ols were synthesized and studied by ^1^H, ^13^C and 2D NMR spectroscopy, and the crystal structure of (±)‐3‐(4‐methylphenyl)‐1‐azabicyclo[2.2.2]octan‐3‐ol was determined by X‐ray diffraction. The combined use of COSY, NOESY and ^1^H–^13^