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1 4 NMR 4.1 Zeeman 1, 13 C, 19 F, 31 P NMR 1 13 C 1/ %&'- 89:;'<= 7%&':#$>?@ 89)A89B.+ " %&' 23456,#$-./01 #$( )*+! %&'!"#$ #E = h $ 2% B 0 B α β ΔE B 0 ΔE B 0 γ gyromagnetic ratio T 1 γ = T 1 s 1 13 C γ = T 1 s 1 h Planck ΔE = h(γ/2π)b 0 = hν 1

2 ΔE ν NMR Fourier FT γ NMR 4.70 T Mz 13 C 50 Mz NMR 4.70 T XX C NMR NMR 0.5 ml CDCl 3 5 mm 4.2 NMR NMR 1 m 300 Mz NMR 2

3 4.2.1 NMR 4.2 NMR NMR 4.2 2,2 1 1 NMR 1/10 6 TMS Si(C 3 ) 4 ppm (parts per million) 3

4 NMR chemical shift NMR ppm δ = TMS / TMS 10 6!"#$ 4.1 C 3 C 2 C Ar C 3 C ± ± ± ± ± ± ± ± 0.3 %&3)45* C= %&'()* 7.0~ ~ ~ ~7.4 C 2 C 2 C 2 C 2 CN 2.1 ± ± ± ± ± 0.3 N 2 C 2 C 2 C C 2 N C 2 X C ± ± ± 0.3 N C ± 0.4 X 3.3 ± 0.3 (X=F: 4.1 ± 0.1) +,-./#$ 012%&#$ R R Ar 9.6 ± ± 0.6 Ar C N 2 CN 2 2~5 4~9 9~13 1~4 5~9 4

5 4.2 2,2 1 1 NMR δ ppm 3.29 ppm C C C C Z C C (Z =, N, X) ! (ppm) C 3 C 2 C sp 2 diamagnetic anisotropy 4.4!"# ()&' ()&' ()&' $%&' $%&' $%&' (a) *+,- (b).-/- (c) *

6 ring current ppm NMR , NMR C Br C C 3 C ,1 1 NMR (270 Mz) 6

7 δ 3.47 singlet 2 δ doublet 1 δ triplet spin spin splitting spin spin coupling spin spin coupling constant J J = 5.5 z J z N N NMR C 3 CC 2 C NMR (270 Mz) 7

8 3 δ δ quartet δ 4.12 C C J = 7.0 z A!"#$ X %$&'()*+,-./0 1./ -"#$ X %$&'()*+,1./0 1"#$ X %$&'()*+,2./0 2./ J J J αα, (αβ, βα), ββ ααα, (ααβ, αβα, βαα), (αββ, βαβ, ββα), βββ (C 3 ) 2 CCl C 6 C

9 z X C Y 6~18 C C 6~8!"#$%& 8~12 2~3 2~3 0~2 X X X 6~12 12~18 7~10 2~3 0~1,-./0123 0~ ~2 0~1.5 'W()*+& < 7 geminal 2 J 3 J C J = 9~12 z J = 10~15 z Karplus A, B, C Karplus 3 J = Acos 2 + Bcos + C 3 J 4 J < 1 z NMR 1 NMR NMR 9

10 NMR 400 Mz ppm ppm 6 7 N + 1 1:6:15:20:15:6:1 6 J = 7.2 z ppm 1.11 ppm C 2.15 ppm 10

11 NMR (400 Mz) ppm J = 5.8 z ppm 6.48 ppm J trans = 14.4, J cis = 6.8, J gem = 2.4 z NMR ,2 1 NMR 11

12 3 C C* C Br a b Br ,2 1 NMR (270 Mz) C C Br Br Me Br Br Br Me a Me b a Br b a b , a 2 J

13 J J (a)!" J > 10 " A " # (b)!" J = 5 " A " # (c)!" J = 2 " A " # J J (d)!" J = 1 " A " # (e)!" J = 0 " A = " # 4.12 ν z p ppm 13

14 4.13 p 1 NMR (400 Mz) 4.13 p 1 NMR J = 8.4 z a ,2 1 C 2 C 2 14

15 C 2 CDCl 3 2,2 1 1 NMR ppm J = 6.2 z 3.29 ppm C 2 2 NMR , NMR CDCl Mz NMR J z 1~10 4 NMR 15

16 b. irradiation NMR 4.15 (a) (b) 1.9 ppm (b) (a) NMR C NMR 12 C NMR 1.11% 13 C NMR 1 16

17 1/ C NMR 1 1 broad-band proton decoupling 13 C 4.4 NE FT NMR 2 13 C 13 C 13 C 13 C NMR 200 ppm C 13 C NMR TMS (C 3 ) 4 Si R C 3 R C 2 R R R C R R R C R C NMR ppm 0 8~35 15~50 20~60 30~40 C I C Br C Cl C N C 0~40 25~65 35~80 40~60 50~80 R C Y R C 65~85 C 100~150 C 110~170 R C R R C 165~ ~ ~215 NMR 13 C 1 1/4 NMR 1/64 1/5800 NE 17

18 13 C sp 2 sp C NMR C NMR 4.17 CDCl 3 13 C NMR 10% 13 C

19 C NMR CDCl 3 13 C NMR NMR saturation relaxation 2 spin-lattice relaxation 19

20 T 1 T 2 T 1 > T 2 NMR T 1 T 1 13 C NMR NE NMR verhauser nuclear verhauser effect, NE C NMR NE 3 13 C NMR NE 1 NMR 4.5 NMR 2D NMR NMR 20

21 NMR 2D NMR 2D NMR NMR 2D NMR 1 1 CSY correlation spectroscopy 1 13 C 1 13 C 13 C 2D NMR C C C NESY nuclear verhauser effect difference spectroscopy NE 1 1 CSY x y 1 NMR CSY a b 3 C 7 3 C b' a' C 3 c c' 3!"#(3-Carene) 6 3 C 7 1 eq ax ax eq 2 C 3 5 C

22 CSY a a δ 1.7~2.3 ppm 2, 2 5, b b c c (ax), 5 (ax), 2 (eq), 5 (eq), 4 22

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