TY - JOUR
T1 - Conformational assignments and a nitrogen inversion process in some 3-acyloxy-1,3-oxazinanes by NMR and X-ray analysis
AU - Hashmi, Syed M.A.
AU - Wazeer, Mohammed I.M.
AU - Hussain, M. Sakhawat
AU - Reibenspies, Joseph H.
AU - Perzanowski, Herman P.
AU - Ali, Sk Asrof
PY - 1999/4
Y1 - 1999/4
N2 - The stereochemistry of the preferred conformers of several 3-acyloxy-1,3-oxazinanes has been established by NMR spectroscopy. A strong anomeric effect stabilizes the conformation having an equatorial orientation of the lone pair on nitrogen. A nitrogen inversion process was found to be the rate-limiting process in the conformational equilibria. The range of ΔG‡ values was found to be 60-71 kJ mol-1. Solid state structures as determined by X-ray diffraction confirm the findings of the NMR study.
AB - The stereochemistry of the preferred conformers of several 3-acyloxy-1,3-oxazinanes has been established by NMR spectroscopy. A strong anomeric effect stabilizes the conformation having an equatorial orientation of the lone pair on nitrogen. A nitrogen inversion process was found to be the rate-limiting process in the conformational equilibria. The range of ΔG‡ values was found to be 60-71 kJ mol-1. Solid state structures as determined by X-ray diffraction confirm the findings of the NMR study.
UR - https://www.scopus.com/pages/publications/0041626603
U2 - 10.1039/a807273f
DO - 10.1039/a807273f
M3 - Article
AN - SCOPUS:0041626603
SN - 0300-9580
SP - 877
EP - 883
JO - Journal of the Chemical Society. Perkin Transactions 2
JF - Journal of the Chemical Society. Perkin Transactions 2
IS - 4
ER -