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Table 6 Theoretical and experimental 1H-NMR chemical shifts (ppm) of 3a–g compounds computed at the level of the DFT/B3LYP/6-311G theory

From: Inhibition of DRP-1 mitochondrial mitophagy and fission by novel α-aminophosphonates bearing pyridine: synthesis, biological evaluations, and computer-aided design

 

Chemical shifts, δ (ppm)

 

                                                      3a

                                                3b

                                            3c

 

Experimental a

Theoretical b

 

Experimental a

Theoretical b

 

Experimental a

Theoretical b

H28, H29 pyridine

7.89 (s), 9.74 (s)

7.38, 8.28

H26, H27 pyridine

7.90 (s), 9.76 (s)

7.39, 8.27

H27, H28 pyridine

7.23 (s), 8.04 (s)

7.36, 8.29

H42substituted phenyl

7.69 (s)

7.83

H40, H41, H42, H43 substituted phenyl

6.89(d), 7.72(d)

6.99, 8.03

H41, H42, H43, H44 substituted phenyl

6.48–7.90 (m)

6.84–8.13 (m)

H43, H44 substituted phenyl

6.92(d), 7.35 (d)

6.87, 7.06

CH29–P proton

6.09 (s)

6.37

CH30–P proton

6.47 (s)

7.30

CH31–P proton

6.46 (s)

6.43

2 × CH2–CH3

3.97–4.03 (m)

4.22–4.95 (m)

O–CH3

3.75 (s)

3.99

O–CH3

3.75 (s)

3.72

2 × CH2–CH3

1.02 (t)

0.97

2 × CH2–CH3

3.83–3.98 (m)

4.04–4.65 (m)

2 × CH2–CH3

3.81–4.01 (m)

4.15–4.45

   

2 × CH2–CH3

0.96–1.17 (m)

0.90–1.32 (m)

2 × CH2–CH3

1.18 (t)

1.01

      

                                                  3d

                                              3e

                                                 3f

 

Experimentala

Theoreticalb

 

Experimentala

Theoreticalb

 

Experimentala

Theoreticalb

H27, H28 pyridine

7.89 (s), 8.91 (s)

7.50, 8.28

H28, H29 pyridine

7.89 (s), 9.63 (s)

7.37, 8.26

H24, H25 pyridine

7.71 (s), 8.08 (s)

7.41, 8.38

H43, H44

substituted phenyl

7.02 (d), 7.39 (d)

7.25, 8.00

H42, H45, H43, H44 substituted phenyl

6.72(d), 7.63(d)

6.62, 7.29

H40 thiophene

7.89 (s)

8.31

H45, H46, H47, H48 substituted phenyl

7.56–8.15 (m)

7.70–7.86 (m)

CH31–P proton

6.47 (s)

6.47

H38, H39 thiophene

6.95 (d), 7.44 (d)

7.18, 7.58

CH32–P proton

5.72 (d)

7.08

N–(CH3)2

2.99 (s)

2.82

CH27–P proton

5.18 (d)

6.74

2 × CH2–CH3

3.84–4.02 (m)

4.03–4.30 (m)

2 × CH2–CH3

3.97–4.03 (m)

4.22–4.95 (m)

2 × CH2–CH3

3.96–3.99 (m)

4.12–4.31

2 × CH2–CH3

1.00 (t), 1.20 (t)

1.10 (t)

2 × CH2–CH3

1.02 (t)

0.97

2 × CH2–CH3

1.06–1.21 (m)

1.04–1.29 (m)

                                                      3g

      
 

Experimentala

Theoreticalb

      

H26, H27 pyridine

7.89 (s), 9.44 (s)

7.38, 8.30

      

H40, H41, H42, H43 substituted phenyl

6.91–8.48 (m)

7.23–8.17 (m)

      

CH29–P proton

6.44 (s)

6.88

      

2 × CH2–CH3

3.80–4.02 (m)

4.19–4.56 (m)

      

2 × CH2–CH3

1.05–1.23 (m)

0.99–1.33

      
  1. Every value is expressed in terms of the TMS chemical shift, calculated at the same theoretical level
  2. aExperimental values of chemical shifts in this work obtained to 500 MHz in DMSO
  3. bTheoretical values of chemical shifts obtained by DFT/B3LYP/6-311G method in DMSO
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BMC Chemistry

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