Propylamine - note the broad and weak NH2 peak, the degree of coupling, and the shift of the methylene protons due to the electronegative nitrogen |
Shifts:
R-N-H: 0.5 - 4 ppm. Variable shifts/broadening for the same reason as alcohols.
Ph-N-H: 3.0 - 5.0 ppm. Deshielded by both anisotropy and resonance.
CH-N: 2.2 - 2.9 ppm
Coupling:
N-H: 50 Hz. Usually not observed. Presumably due to proton exchange.
N-C-H: About 0 Hz. Usually not observed. I'm unsure why. Perhaps due to resonance creating (+)N=C hence proton exchange..
H-C-N-H: About 0 Hz. Usually not observed. Presumably due to proton exchange.
As with alcohols, adding D2O to the reaction mixture will cause the NH peak to shrink or vanish.
The quadrupole on N kills coupling.
ReplyDelete