Conformational equilibrium and dynamic behavior of bis-N-triflyl substituted 3,8-diazabicyclo[3.2.1]octane

Bagrat A Shainyan; Mikhail Yu Moskalik; Matthias Heydenreich; Erich Kleinpeter

doi:10.1002/mrc.4086

Conformational equilibrium and dynamic behavior of bis-N-triflyl substituted 3,8-diazabicyclo[3.2.1]octane

Magn Reson Chem. 2014 Aug;52(8):448-52. doi: 10.1002/mrc.4086. Epub 2014 Jun 10.

Authors

Bagrat A Shainyan¹, Mikhail Yu Moskalik, Matthias Heydenreich, Erich Kleinpeter

Affiliation

¹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Science, 1 Favorsky Street, 664033, Irkutsk, Russian Federation.

PMID: 24915750
DOI: 10.1002/mrc.4086

Abstract

Restricted rotation about the N-S partial double bonds in a bis-N-triflyl substituted 3,8-diazabicyclo[3.2.1]octane derivative 1 has been frozen at low temperature (ΔG(≠) = 11.6 kcal mol(-1)), and the existence of all four rotamers about the two N-S bonds, 3-in,8-in, 3-in,8-out, 3-out,8-in, and 3-out,8-out, respectively, proved experimentally by NMR spectroscopy and theoretically by DFT and MP2 calculations.

Keywords: 13C; 19F; 1H; Conformational equilibrium; Dynamic NMR; NMR; restricted N-S rotation.