O H H

piperine 15 12a 10a

Clauss(cgf) 070107 21 14 12 10 6
15mg in 100% CDCl3 13 11 7
O
20 N 5 1
16 2
19 17 H H 8 4
18 13a 11a 9 O
3

9 10
6 11 13

CHCl3 8

12

500 MHz

300 MHz

7.6 7.4 7.2 7.0 6.8 6.6 6.4 6.2 PPM

piperine

4.24

4.21
Clauss(cgf) 070107
15mg in 100% CDCl3
1H spectrum at 500 MHz

2.17
2.05
1.99
1.10

1.09
1.05

1.04
1.00
1.00

8 7 6 5 4 3 2 1 0 PPM
 O H H
15 12a 10a

piperine 21 14 12 10 6
O
20 N 13 11 7 5 1
Clauss(cgf) 070107 2 16 2
15mg in 100% CDCl3 19 17 H H 8 4
1H spectrum at 500 MHz 18 13a 11a 9 O
3

9
6 10
11
8
all expansions
20Hz/cm unless
otherwise noted
13
7.00 6.95 6.90 6.85 6.80 6.75 PPM
18 +
20
60Hz/cm
17 +
21 19
12

6.480
6.470
6.460
6.450
6.440 PPM -OH

1.85 1.80 1.75 1.70 1.65 1.60 1.55 PPM

7.487.467.447.427.407.38 PPM 3.803.753.703.653.603.553.50PPM

8 7 6 5 4 3 2 1 0 PPM
 piperine
Clauss(cgf) 070107
15mg in 100% CDCl3

1H gcosy spectrum
at 500 MHz
F1
(ppm)

3
O H H
15 12a 10a

21 14 12 10 6 4
O
20 N 13 11 7 5 1
16 2
19 17 H H 8 4
13a 11a O 5
18 9
3

8 7 6 5 4 3 2 1 0
F2 (ppm)
 piperine
Clauss(cgf) 070107
15mg in 100% CDCl3

1H gcosy expansion
at 500 MHz
F1
(ppm)
O H H
15 12a 10a

21 14 12 10 6
O
20 N 13 11 7 5 1
16 2
6.6
19 17 H H 8 4
18 13a 11a 9 O
3

6.8

7.0

7.2

7.4

7.4 7.2 7.0 6.8 6.6 F2 (ppm)

 piperine
Clauss(cgf) 070107
15mg in 100% CDCl3

1H HSQCAD F1
(1-bond 1H-13C correlation) (ppm)
at 500 MHz

-CH2- show in red 40

-CH3, >CH- in blue

60
O H H
15 12a 10a

21 14 12 10 6
O 80
20 N 13 11 7 5 1
16 2
19 17 H H 8 4
18 13a 11a 9 O
3 100

120

140

160

8 7 6 5 4 3 2 1
F2 (ppm)
 piperine
Clauss(cgf) 070107
15mg in 100% CDCl3

expansion of 1H HSQCAD F1
(1-bond 1H-13C correlation) 2 (ppm)
at 500 MHz
6 9
This adiabatic experiment 110
inverts -CH2-, show in red.

-CH3 and >CH- are left 13

positive in the experiment, 8 120

and are shown in blue. 11

130

10
12 140

O H H
15 12a 10a

21 14 12 10 6 150
O
20 N 13 11 7 5 1
16 2
19 17 H H 8 4
18 13a 11a 9 O 160
3

7.4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 F2 (ppm)

 piperine
Clauss(cgf) 070107
15mg in 100% CDCl3

1H gHMBCAD (long-range F1
1H-13C correlation) (ppm)
at 500 MHz

O H H 40
15 12a 10a

21 14 12 10 6
O
20 N 13 11 7 5 1 60
16 2
19 17 H H 8 4
18 13a 11a 9 O
3
80

100

120

140

160

8 7 6 5 4 3 2 F2 (ppm)
 10 2
9
11
piperine 6 13
Clauss(cgf) 070107 8
12
15mg in 100% CDCl3

O H H
15 12a 10a F1
12 10
(ppm)
21 14 6
O
20 N 13 11 7 5 1 C6
16 2 C9
19 17 H H 8 4 110
18 13a 11a 9 O
3

C13 120
expansion of 1H C8
gHMBCAD (n-bond C11
1H-13C correlation)
at 500 MHz C7 130

1-bond artifacts C10

(doublets in the F2 140
dimension split by C12
JCH~160Hz) have
been colored yellow. C4,C5
150

160

C14

7.4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 F2 (ppm)