261
6.1.3 Carbonyl and Thiocarbonyl Derivatives
Amides and Lactams. 15 N Chemical Shifts and Coupling Constants (δ
in ppm relative to CH 3 NO 2 , J in Hz)
NH
O
N
O
N
O
N
O
H
N
O
H
NH
O
NH
O
NH 2
O
-301.4
(acetone)
1 J NH -86.4
(CDCl 3 )
-327.0
(DMSO)
1 J NH -75.6
(CDCl 3 )
-326.5
(neat)
1 J NH -76.5
(CDCl 3 )
(Z) -270.1 (neat)
2 J NH 15.6
2 J NCH 3
1.4
-253.0 (Z)
-254.0 (E)
-233.4 (Z)
-231.1 (E)
(neat)
-273.2 (CCl 4 )
1 J NH -93.0
2 J NH 1.0
-271.7
-275.8 (CCl 4 )
-275.1
(CCl 4 )
-275.7 (DMSO) -248.7 (neat)
-281.0 (neat)
-249.6 (neat) -285.8 (neat)
-275.1 (EtOH) -275.2 (EtOH)
-277.7 (CCl 4 )
-277.7
(CCl 4 )
-282.3 (CCl 4 )
-282.3
(CCl 4 )
-320.4
(acetone)
NH 2
O
NH 2
NO 2
NH 2
NH 2
Cl
H
NH 2
O
NH 2
O
NH 2
O
NH 2
O
H
N
O
-10.2
-267.6 (neat)
1 J NH(syn) -88.3
1 J NH(anti) -92.7
2 J NH 14.6
-269.5 (neat)
1 J NH(syn) -88.4
1 J NH(anti) -90.9
3 J NH -1.3
NH
O
NH
O
NH
O
(E) -271.9 (neat)
2 J NH 15.1
2 J NCH 3
1.4
H
O
NH
CH 3
H
O
N
H
CH 3
≈ 90%
≈ 10%
H
NH
O
NH
O
NH
O
6.1 15 N NMR Spectroscopy