TY - JOUR
T1 - Nitrogen inversion and N-O bond rotation in some hydroxylamine and isoxazolidine derivatives
AU - Hassan, Azfar
AU - Wazeer, Mohamed I.M.
AU - Perzanowski, Herman P.
AU - Ali, Sk Asrof
PY - 1997/3
Y1 - 1997/3
N2 - A series of trisubstituted hydroxylamine derivatives, both cyclic and acyclic, has been prepared. The energy barriers in these hydroxylamines are found to be dominated either by nitrogen inversion or N-O bond rotation depending on the nature of the substituents attached to the nitrogen. In several series of compounds, having XC6H4CH2 substituents attached to nitrogen, Hammett free energy correlations are obtained with positive ρ values, indicating increased electron density at the transition state for the inversion process. Isoxazolidines with C(5) ethoxy substituents demonstrate a strong anomeric effect.
AB - A series of trisubstituted hydroxylamine derivatives, both cyclic and acyclic, has been prepared. The energy barriers in these hydroxylamines are found to be dominated either by nitrogen inversion or N-O bond rotation depending on the nature of the substituents attached to the nitrogen. In several series of compounds, having XC6H4CH2 substituents attached to nitrogen, Hammett free energy correlations are obtained with positive ρ values, indicating increased electron density at the transition state for the inversion process. Isoxazolidines with C(5) ethoxy substituents demonstrate a strong anomeric effect.
UR - https://www.scopus.com/pages/publications/0001820418
U2 - 10.1039/a604719j
DO - 10.1039/a604719j
M3 - Article
AN - SCOPUS:0001820418
SN - 0300-9580
SP - 411
EP - 418
JO - Journal of the Chemical Society. Perkin Transactions 2
JF - Journal of the Chemical Society. Perkin Transactions 2
IS - 3
ER -