60
3 Combination Tables
3.6 Halogen Compounds
Assignment
Range
Comments
al C–F
(C)=C–F
C=(C–F)
ar C–F
ar C–(C–F)
70–100 ppm
125–175 ppm
65–115 ppm
140–165 ppm
105–135 ppm
CF 3 : ≈115 ppm
Coupling with 19 F (isotope abundance,
100%; I = 1/2): | 1 J CF | 100–300 Hz
| 2 J CF | 10–40 Hz
| 3 J CF | 5–10 Hz
| 4 J CF | 0–5 Hz
al C–Cl
(C)=C–Cl
C=(C–Cl)
ar C–Cl
ar C–(C–Cl)
30–60 ppm
100–150 ppm
100–155 ppm
120–150 ppm
125–135 ppm
al C–Br
(C)=C–Br
C=(C–Br)
ar C–Br
ar C–(C–Br)
10–45 ppm
90–140 ppm
90–140 ppm
110–140 ppm
125–135 ppm
al C–I
(C)=C–I
C=(C–I)
ar C–I
ar C–(C–I)
-20 to +30 ppm
60–110 ppm
120–150 ppm
85–115 ppm
125–145 ppm
CH 2 –F
≈4.3 ppm
Coupling with 19 F (isotope abundance,
100%; I = 1/2): | 2 J HF | 40–80 Hz
| 3 J HF | 0–50 Hz
| 4 J CF | 0–5 Hz
CH 2 –Cl
CH 2 –Br
CH 2 –I
≈3.5 ppm
≈3.4 ppm
≈3.1 ppm
H–CX=C
5.5–8.0 ppm
Similar shifts for all halogens
H–C=CF
H–C=CCl
H–C=CBr
H–C=CI
4.0–6.0 ppm
4.5–6.5 ppm
5.0–7.0 ppm
5.5–7.5 ppm
H–phenyl–hal
7.0–7.6 ppm
Shielding by F in ortho and para positions;
small effects for Cl and Br; deshielding by
I in ortho, and shielding in meta position
C–F st
C–Cl st
C–Br st
C–I st
1400–1000 cm -1
850–600 cm -1
700–500 cm -1
650–450 cm -1
Strong
Strong
Strong
Strong
13 C
1 H
IR