2-2 1h nmr spectrum of 3a in cdcl3

14
2-2 PPM 15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1 0.9037 1.9814 2.0563 1.0000 0.9764 2.9306 6.3632 3.1204 13.863 7.713 7.542 5.300 4.725 4.262 3.934 3.881 3.739 1 H NMR spectrum of 3a in CDCl 3 x tol x

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Page 1: 2-2 1H NMR spectrum of 3a in CDCl3

2-2

PPM15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 -1

0.90

37 1.98

142.

0563

1.00

00

0.97

642.

9306

6.36

323.

1204

13.8

63

7.7

13 7

.542

5.3

00

4.7

25 4

.262

3.9

34 3

.881

3.7

39

1H NMR spectrum of 3a in CDCl3

x tol

x

Page 2: 2-2 1H NMR spectrum of 3a in CDCl3

2-31H NMR spectrum of 3a (top) and acenaphthenequinonemonophenylhydrazone (bottom) in C6D6

PPM15.0 14.0 13.0 12.0 11.0 10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 -1.0

14.206

13.349

x tol

x

Page 3: 2-2 1H NMR spectrum of 3a in CDCl3

2-413C NMR spectrum of 3a in CDCl3

PPM200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10

190.518

185.614

170.254

168.839

167.153

164.874

63.861

55.856

54.326

54.203

53.298

52.878

43.795

x tol

x

x tol

x

x

x

Page 4: 2-2 1H NMR spectrum of 3a in CDCl3

2-5DEPT135 NMR spectrum of 3a in CDCl3

PPM200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0

129.

892

124.

908

115.

324

54.

325

54.

205

53.

298

52.

881

43.

774

29.

670

x

x

x xx

Page 5: 2-2 1H NMR spectrum of 3a in CDCl3

2-6HMQC NMR spectrum of 3a (13C enriched) in C6D6

Page 6: 2-2 1H NMR spectrum of 3a in CDCl3

2-7HMBC NMR spectrum of 3a (13C enriched) in C6D6

Page 7: 2-2 1H NMR spectrum of 3a in CDCl3

2-8HMBC NMR spectrum of 3a (13C enriched) in C6D6

5.5 5.0 4.519

018

017

016

015

014

013

0

PPM

151.74155.06

128.66

145.24

135.77

147.88

2JCH

2JCH

3JCH

3JCH

3JCH3JCH

C(5)

C(10)

C(7)C(11)C(9)C(6)

Page 8: 2-2 1H NMR spectrum of 3a in CDCl3

2-9INADEQUATE 1D spectrum of 3a (13C enriched) in C6D6 (Jcc=57 Hz)

PPM200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10

190.

890

186.

177

154.

975

151.

679

142.

835

140.

991

138.

172

131.

972

131.

614

129.

321

126.

740

126.

397

43.

957

Page 9: 2-2 1H NMR spectrum of 3a in CDCl3

2-10Selective INADEQUATE 1D spectrum of 3a (13C enriched) in C6D6(OBS2: 190.9 ppm, Jcc=57 Hz)

PPM200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0

128.645

128.

645

Page 10: 2-2 1H NMR spectrum of 3a in CDCl3

2-11Selective INADEQUATE 1D spectrum of 3a (13C enriched) in C6D6(OBS2: 186.2 ppm, Jcc=57 Hz)

PPM200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0

136.504

135.904

136.

504

135.

904

Page 11: 2-2 1H NMR spectrum of 3a in CDCl3

2-12Selective INADEQUATE 1D spectrum of 3a (13C enriched) in C6D6(OBS2: 44.0 ppm, Jcc=77 Hz)

PPM200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0

155.032

151.716

155.

032

151.

716

Page 12: 2-2 1H NMR spectrum of 3a in CDCl3

2-13Selective INADEQUATE 1D spectrum of 3a (13C enriched) in C6D6(OBS2: 155.1 ppm, Jcc=57 Hz)

PPM200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0

145.867

145.189

128.880

128.403

44.095

43.828

145.

867

145.

189

128.

880

128.

403

44.0

9543

.828

Page 13: 2-2 1H NMR spectrum of 3a in CDCl3

2-14Selective INADEQUATE 1D spectrum of the 13C enriched 3a in C6D6(OBS2: 151.7 ppm, Jcc=57 Hz)

PPM200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0

148.074

147.716

135.990

135.534

44.087

43.824

148.

074

147.

716

135.

990

135.

534

44.0

8743

.824

Page 14: 2-2 1H NMR spectrum of 3a in CDCl3

2-15ES-Mass spectrum (neg.) of 3a

529R

600 650 700 750 800 850 900 950 1000 1050 1100 1150 1200 1250 1300 1350 1400 1450 1500 1550 1600m/z0

100

%

020711_7 83 (1.522) Cm (71:85) TOF MS ES- 3.88e31144.42

3879

1143.401938

1145.441738

1160.411212

1161.44958