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Table 5 Significant donor–acceptor interactions of 3a/3b and their second order perturbation energies calculated at B3LYP level using 6-31G (d, p) basis set

From: Synthesis and structural properties of 2-((10-alkyl-10H-phenothiazin-3-yl)methylene)malononitrile derivatives; a combined experimental and theoretical insight

Donor (i) (occupancy)

Type

EDA, % EDB, %

Acceptor (j) (occupancy)

Type

EDA, % EDB, %

E(2)a (kcal/mol)

Ej–E bi

(a.u.)

F (i, j) (a.u.)

BD C3–C4 1.97721

σ

49.64 50.36

BD* C2–C3 0.02660

σ*

51.36 48.64

3.16

1.25

0.056

BD C4–C5 1.97419

σ

48.62 51.38

BD* C3–C4 0.01233

σ*

50.36 49.64

2.53

1.29

0.051

BD C4–C5 1.59136

Ï€

44.97 55.03

BD* C13–C14 0.24073

Ï€*

59.29 40.71

22.02

0.27

0.071

BD C2–C3 1.97034

σ

48.64 51.36

BD* C3–C4 0.01233

σ*

50.36 49.64

2.69

1.30

0.053

BD C2–C3 1.60070

Ï€

53.51 46.49

BD* C4–C5 0.42336

Ï€*

55.03 44.97

25.19

0.28

0.076

BD C1–C2 1.97300

σ

50.22 49.78

BD* C2–C3 0.02660

σ*

51.36 48.64

3.44

1.26

0.059

BD C1–C6 1.97721

σ

50.97 49.03

BD* C5–C6 0.02189

σ*

50.82 49.18

2.95

1.27

0.055

BD C1–C6 1.71641

Ï€

54.39 45.61

BD* C2–C3 0.40194

Ï€*

46.49 53.51

19.81

0.29

0.069

BD C5–C6 1.97016

σ

49.18 50.82

BD* C4–C5 0.02494

σ*

51.38 48.62

3.18

1.24

0.056

BD C7–C12 1.97320

σ

49.77 50.23

BD* C11–C12 0.02533

σ*

48.64 51.36

3.93

1.28

0.063

BD C7–C8 1.97672

σ

51.41 48.59

BD* C7–C12 0.03387

σ*

50.23 49.77

4.58

1.26

0.068

BD C7–C8 1.69501

Ï€

53.56 46.44

BD* C11–C12 0.38891

Ï€*

51.02 48.98

20.16

0.28

0.069

BD C11–C12 1.66680

Ï€

48.98 51.02

BD* C9–C10 0.33937

Ï€*

50.66 49.34

20.47

0.29

0.069

BD C9–C10 1.66550

Ï€

49.34 50.66

BD* C7–C8 0.38725

Ï€*

46.44 53.56

22.74

0.27

0.071

BD C13–C14 1.81237

Ï€

40.71 59.29

BD* C15–N2 0.08582

Ï€*

54.47 45.53

19.91

0.39

0.081

BD C13–C14 1.81237

Ï€

40.71 59.29

BD* C16–N3 0.08857

Ï€*

54.71 45.29

20.52

0.40

0.083

LP N1 1.69519

  

BD* C2–C3 0.40194

Ï€*

46.49 53.51

31.28

0.27

0.084

LP N1 1.69519

  

BD* C11–C12 0.38891

Ï€*

51.02 48.98

24.09

0.28

0.075

LP S1 1.84528

  

BD* C1–C6 0.34392

Ï€*

45.61 54.39

12.09

0.27

0.053

LP S1 1.84528

  

BD* C7–C8 0.38725

Ï€*

46.44 53.56

11.23

0.27

0.053

  1. aE(2) means energy of hyperconjucative interactions (stabilization energy)
  2. bEnergy difference between donor (i) and acceptor (j) NBO orbitals