NMR Spectra

NMR spectroscopy is commonly used for the identification of isomeric tetrazolium salts. There are significant differences in the chemical shifts of C-methyl and ^-methyl protons as shown in Table 4 for compounds 128

NMR Spectra

NMR Spectra

(126)

 

(127)

 

Scheme 18

 

CH3

СНзСОСН^® ^CH3

N N

I I

N-=-N

(128)

 

NMR Spectra

Compound

О

ffi

N-CH3

C-CH3

128

6.00

4.44

2.92

129

6.12

4.37

2.86

 

Table 5. ‘H-NMR Chemical Shifts (5) of Methyl-Substituted

Tetrazoliums 130-135

Compound

1-CH3

3-CH3

4-CH3

5-CH3

130

4.31

4.58

131

4.33

4.60

132

4.35

133

4.72

134

4.30

2.90

135

4.62

2.78

 

NMR SpectraNMR Spectra

NMR Spectra

(136) (137)

 

Compound

X

1-CH3

3-CH3

4-CH3

136

H

4.40

4.40

136

no2

4.45

4.45

137

H

4.60

4.80

137

no2

4.65

4.90

NMR Spectra NMR Spectra

Table 7. ‘H-NMR Chemical Shifts (5) of N-Phenyl Tetrazoliums 138 and 139

Compound

R

H(R)

О

ffi

О

ffi

H(Ph-2’/6′)

138

H

1 1 .30

1.80

4.96

8.02

138

CH3

2.93

1.73

4.73

7.75

138

CH2C1

5.31

1.76

4.88

7.78

139

H

2.93

1.82

5.07

8.26

139

CH2C1

5.45

1.80

5.03

8.24

Подпись: (140)

(141)

Compound

H-5

Ph-2′-H

Ph-3 ‘/14’-H

140

10.74

7.81

7.56

141

10.26

8.26

7.81

Table 9. 13C-NMR Chemical Shifts (5) of Methyl-Substituted

Tetrazoliums 130-135

Compound

1-CH3

3-CH3

4-CH3

5-CH3

Ring

130

37.80

38.80

162.7

131

38.80

37.75

162.7

132

38.33

142.1

133

44.18

149.3

134

37.04

8.96

152.6

135

44.10

9.93

159.1

Table 10.

15N-NMR Chemical Shifts (5) of Methyl-Substituted Tetrazoliums 130-132

Compound

N1

N2

N3

N4

130

-71.5

— 101.2

— 17.5

— 148.7

131

-148.1

-17.9

— 101.2

-76.1

132

-127.5

-22.2

— 14.4

— 142.5

and 129,187 Table 5 for 130—135,219 and in Table 6 for 136 and 137.180-215 The 5-ring proton chemical shifts in 5-unsubstituted tetrazolium as well as the ortho proton in phenyl substituents at the 5-position are sensitive to N-substituents and substitution patterns as shown in Table 7 for 138 and 139 and in Table 8 for 140 and 141.181-218

Carbon-13 NMR has been used in the study of thiolate and disub — stituted tetrazolium derivatives.217-219 The chemical shifts of both the substituent and ring carbons show strong sensitivity to substitutents as shown in Table 9 for 130—135.219 Tetrazolium salts have also been studied by nitrogen-15 NMR (Table 10).220’221

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