Supporting Information for. Department of Chemistry, Vanderbilt University, Nashville, TN 37235
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1 Supporting Information for Functional Group Transformations in Derivatives of 1,4-Dihydrobenzo[1,2,4]triazinyl Radical Agnieszka Bodzioch, a, Minyan Zheng, a Piotr Kaszyński, a,b * Greta Utecht a a Organic Materials Research Group Department of Chemistry, Vanderbilt University, ashville, T b Faculty of Chemistry, University of Łódź, Tamka 12, Łódź, Poland Table of Content: 1. 1 H MR and 13 C MR spectra for selected compounds.s2 2. Thermodynamic data for formation of 32.S66 3. Partial data for TD-DFT calculation (B3LYP/6-31G(d,p)) for 1 S67 4. Theoretical hfcc values for model radicals S75 5. Simulation of EPR spectra S75 6. Archive data for DFT calculations S76 S 1
2 1. 1 H MR and 13 C MR spectra for selected compounds 6a Ph(O)CO CF 3 H H OC(O)Ph S 2
3 6b S 3
4 Ph(O)CO CF 3 H H OCH 2Ph S 4
5 6c S 5
6 I CF 3 H H OCH 2 Ph S 6
7 6d S 7
8 I CF 3 H H I S 8
9 6e S 9
10 CF 3 H H O 2 S 10
11 7a S 11
12 Ph(O)CO I H H OC(O)Ph S 12
13 7d S 13
14 I I H H I S 14
15 8d S 15
16 I F H H I S 16
17 9a S 17
18 Ph(O)CO H H OC(O)Ph S 18
19 9b S 19
20 Ph(O)CO H H OCH 2 Ph S 20
21 11a S 21
22 O H CF 3 OC(O)Ph S 22
23 11b S 23
24 O H CF 3 OCH 2 Ph S 24
25 11d S 25
26 O H CF 3 I S 26
27 11e S 27
28 S 28
29 12a S 29
30 O H I OC(O)Ph S 30
31 12d S 31
32 O H I I S 32
33 13d S 33
34 O H F I S 34
35 14a S 35
36 O H OC(O)Ph S 36
37 14b S 37
38 O H OCH 2 Ph S 38
39 15a S 39
40 Cl CF 3 OC(O)Ph S 40
41 15b S 41
42 Cl CF 3 OCH 2 Ph S 42
43 S 43
44 15d Cl CF 3 I S 44
45 15e S 45
46 Cl CF 3 O 2 S 46
47 16d S 47
48 Cl I I S 48
49 17d S 49
50 Cl F I S 50
51 18a S 51
52 Cl OC(O)Ph S 52
53 18b S 53
54 Cl OCH 2 Ph S 54
55 22a S 55
56 F 3 C O 2 I S 56
57 22b S 57
58 F 3 C O 2 OCH 2 Ph S 58
59 23a S 59
60 F 3 C O 2 H 2 I S 60
61 23b S 61
62 F 3 C O 2 H 2 OCH 2 Ph S 62
63 26 S 63
64 O H H OCH 2 Ph OCH 2 Ph S 64
65 S 65
66 2. Thermodynamic data for formation of 1,3-diphenyl-1,4-dihydrobenzo[1,2,4]triazine 32 Z a 5 Ph Ph Z H Ph Ph 29 Me 3 H 31 Me 3 H Z Ph Z H Ph 29[H + ] H Ph 31[H + ] Ph H Me 3 a, Z = H b, Z = OH c, Z = C Figure S1. Proposed mechanism for the formation of 1,3-diphenyl-1,4- dihydrobenzo[1,2,4]triazine 32. Z Ph 32 H Ph Table S1. Thermodynamic data for formation of 1,4-dihydrobenzo[1,2,4]triazine 32 from 29. Z ΔH (upper) and ΔG 298 (lower) in CH 2 Cl 2 /kcal mol -1 a,h b,oh c,c [H + ] 31[H + ] [H + ] 29[H + ] 30[H + ] 29[H + ] 31[H + ] S 66
67 3. Partial data for TD-DFT calculation (B3LYP/6-31G(d,p)) for 1r and 4x. α-homo-1, E = ev α -HOMO, E = ev α -LUMO, E = ev α -LUMO+1, E = ev β -HOMO-1, E = ev β-homo, E = ev β-lumo, E = ev β-lumo+1; E = ev Figure S2. B3LYP/6-31G(2d,p) derived contours and energies of frontier molecular orbitals for 1r. S 67
68 β-homo-1; E = ev Figure S3. B3LYP/6-31G(2d,p) derived contour and energies of frontier molecular orbitals for 4x ! /L mol -1 cm n 1r wavelength /nm Figure S4. Magnified absorption spectra for 1r and 4n. Excitation energies and oscillator strength 1r Excited State 1: A ev nm f= <S**2>= A ->144A A ->146A B ->143B B ->143B This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: A 142A ->144A ev nm f= <S**2>=1.135 S 68
69 143A ->144A A ->145A B ->143B B ->143B B ->143B B ->144B Excited State 3: A 141A ->145A A ->144A A ->144A A ->145A B ->143B B ->145B B ->143B B ->144B ev nm f= <S**2>=1.458 Excited State 4: A ev nm f= <S**2>= A ->144A A ->146A A ->144A A ->146A B ->143B B ->143B B ->144B B ->145B B ->146B Excited State 5: A 143A ->145A B ->143B B ->143B B ->143B B ->143B Excited State 6: A 141A ->145A A ->145A B ->143B B ->143B B ->143B B ->143B B ->143B B ->143B B ->145B ev nm f= <S**2>= ev nm f= <S**2>=0.881 S 69
70 Excited State 7: A 141A ->145A A ->145A A ->147A A ->148A B ->143B B ->143B B ->143B B ->143B B ->144B B ->145B B ->143B ev nm f= <S**2>=1.721 Excited State 8: A ev nm f= <S**2>= A ->145A A ->146A B ->143B B ->143B B ->143B B ->143B B ->145B B ->143B Excited State 9: A ev nm f= <S**2>= A ->144A A ->146A A ->147A A ->148A A ->151A A ->152A B ->143B Excited State 10: A 138A ->144A A ->145A A ->146A A ->144A A ->145A A ->146A A ->147A A ->148A A ->153A B ->146B Excited State 11: A 134A ->144A ev nm f= <S**2>= ev nm f= <S**2>=2.004 S 70
71 138A ->144A A ->150A A ->144A A ->146A A ->151A A ->152A A ->153A A ->146A A ->147A A ->148A B ->144B B ->150B B ->143B B ->151B B ->144B B ->144B B ->146B B ->152B B ->153B Excited State 12: A 142A ->146A A ->146A A ->147A A ->148A A ->152A B ->143B B ->143B B ->144B B ->146B Excited State 13: A 138A ->144A A ->144A A ->146A A ->146A B ->143B B ->144B B ->143B B ->146B Excited State 14: A 142A ->144A B ->143B B ->143B B ->143B ev nm f= <S**2>= ev nm f= <S**2>= ev nm f= <S**2>=0.859 S 71
72 4x 140B ->143B B ->144B B ->144B Excited State 1: A ev nm f= <S**2>= A -> 92A B -> 91B This state for optimization and/or second-order correction. Total Energy, E(TD-HF/TD-KS) = Copying the excited state density for this state as the 1-particle RhoCI density. Excited State 2: A 91A -> 92A A -> 94A B -> 91B B -> 91B B -> 91B Excited State 3: A 87B -> 91B B -> 91B B -> 91B Excited State 4: A 91A -> 93A A -> 94A B -> 91B B -> 91B B -> 91B B -> 91B Excited State 5: A 90A -> 92A A -> 93A A -> 94A B -> 91B B -> 91B B -> 91B B -> 91B B -> 92B Excited State 6: A 90A -> 92A A -> 93A ev nm f= <S**2>= ev nm f= <S**2>= ev nm f= <S**2>= ev nm f= <S**2>= ev nm f= <S**2>=1.554 S 72
73 91A -> 94A A -> 96A B -> 95B B -> 91B B -> 91B B -> 92B Excited State 7: A 88A -> 95A A -> 92A A -> 97A A -> 93A A -> 94A A -> 97A B -> 95B B -> 91B B -> 92B B -> 97B Excited State 8: A 90A -> 92A A -> 93A A -> 94A A -> 96A B -> 91B B -> 91B B -> 91B B -> 91B B -> 91B Excited State 9: A 85A -> 93A A -> 94A A -> 95A A -> 96A A -> 97A B -> 91B B -> 93B B -> 91B B -> 91B B -> 94B B -> 97B B -> 94B Excited State 10: A 91A -> 95A ev nm f= <S**2>= ev nm f= <S**2>= ev nm f= <S**2>= ev nm f= <S**2>=0.904 S 73
74 91A -> 96A B -> 91B B -> 92B Excited State 11: A 85A -> 93A A -> 94A A -> 94A A -> 96A A -> 96A A -> 97A B -> 92B B -> 93B B -> 91B B -> 95B B -> 91B B -> 94B B -> 96B Excited State 12: A 90A -> 92A A -> 96A A -> 97A B -> 92B B -> 93B B -> 91B B -> 91B Excited State 13: A 84B -> 91B B -> 91B B -> 91B Excited State 14: A 85A -> 93A A -> 94A A -> 94A A -> 96A A -> 92A A -> 94A A -> 95A A -> 97A B -> 91B B -> 91B B -> 93B B -> 94B ev nm f= <S**2>= ev nm f= <S**2>= ev nm f= <S**2>= ev nm f= <S**2>=1.356 S 74
75 90B -> 92B Theoretical hfcc values for model radicals Table S2. Theoretical hyperfine coupling constants (G) for selected radicals. X F 3 C Y Heterocyclic ring CF 3 at (1) at C(3) compound a (1) a (2) a (4) a H(5) a H(6) a H(8) a F a Ho a Hm a Hp a Ho a Hm 1e X=H, Y=O 2 1t X=H, Y=H 2 1y X=H 2, Y=O 2 1 X=H, Y=OMe 1 X=H, Y=O- a B3LYP/EPR-II//B3LYP/6-31G(2d,p). The hfcc calculated by averaging values for equivalent nuclei. 5. Simulation of EPR spectra Simulation of the EPR spectra was done with the PEST program (EPR-WinSim.2002 version 0.98 for Windows; available at: using results of B3LYP/EPR-II//B3LYP/6-31G(2d,p) for initial input. The resulting hfcc values were perturbed until the global minimum for the fit was achieved. Spectra used for simulation were generated by reflection of the left half of each spectrum. S 75
76 Figure S5. A comparison for experimental, simulate and difference spectra for selected radicals. 6. Archive files for DFT calculations 1e 1\1\GIC-OCTOPUS\FOpt\UB3LYP\6-31G(2d,p)\C20H12F34O2(2)\PIOTR\20-Feb- 2014\0\\#P B3LYP/6-31G(2d,p) FOpt=tight freq(noraman) SCF=Direct #P Ge om=(odistance,oangle) fcheck\\7-cf3-1-ph-3-pho2-benzotrazinyl, C1\\ 0,2\C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \, , , \, , , \H, , , \C, , , \, , , \C, , , \C, , , \C, , S 76
77 , \C, , , \C, , , \C, , , \H, , , \H, , , \H, , , \H, , , \C, , , \ C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \H, , , \H, , , \H, , , \H, , , \C, , , \F, , , \F, , , \F, , , \, , , \O, , , \O, , , \H, , , \\Version=EM64 L-G09RevC.01\State=2-A\HF= \S2= \S2-1=0.\S2A= \RMSD=4.844e-09\RMSF=4.692e-07\Dipole= , , \Quadrupole= , , , , , \PG=C01 1r 1\1\GIC-OCTOPUS\FOpt\UB3LYP\6-31G(2d,p)\C36H21F33(2)\PIOTR\23-Mar-20 14\0\\#P B3LYP/6-31G(2d,p) FOpt=tight freq(noraman) SCF=Direct #P Geom =(odistance,oangle) fcheck\\7-cf3-1,3-(phccph)-benzotrazinyl, C1\\0, 2\, , , \, , , \C, , , \, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \H, , , \H, , , \H, , , \H, , , \H, , , \H, , , \H, , , \H, , , \H, , , \H, , , \C, , , \F, , , \F, , , \F, , , \C, , , \C, , , \C, , , \ C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \H, , , \H, , , \H, , , \H, , , \C, , , \C, , , \C, , , \C,2.5 S 77
78 , , \C, , , \C, , , \H, , , \H, , , \H, , , \H, , , \H, , , \\Versio n=em64l-g09revc.01\state=2-a\hf= \s2= \s2-1=0.\s2a= \RMSD=1.703e-09\RMSF=8.807e-07\Dipole= , , \Quadrupole= , , , , , \PG=C01 [X(C36H21F33)]\\ 1t 1\1\GIC-OCTOPUS\FOpt\UB3LYP\6-31G(2d,p)\C20H14F34(2)\PIOTR\21-Feb-20 14\0\\#P B3LYP/6-31G(2d,p) FOpt=tight freq(noraman) SCF=Direct #P Geom =(odistance,oangle) fcheck\\7-cf3-1-ph-3-phh2-benzotrazinyl, C1\\0, 2\C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \, , , \, , , \H, , , \C, , , \, , , \C, , , \ C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \H, , , \H, , , \H, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \H, , , \H, , , \H, , , \H, , , \C, , , \F, , , \F, , , \F, , , \, , , \H, , , \H, , , \H, , , \\Version=EM6 4L-G09RevC.01\State=2-A\HF= \S2= \S2-1=0.\S2A= \RMSD=7.030e-09\RMSF=3.690e-07\Dipole= , , \Quadrupole= , , , , , \PG=C01 1y 1\1\GIC-OCTOPUS\FOpt\UB3LYP\6-31G(2d,p)\C20H13F35O2(2)\PIOTR\18-Apr- 2014\0\\#P B3LYP/6-31G(2d,p) FOpt=tight SCF=Direct #P Geom=(oDistance,oAngle) fcheck\\7-cf3-1-h2ph-3-pho2-benzotrazinyl, C1\\0,2\C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \, , , \, , , \H, , , \C, , , \, , , \C, , , \C, , , \C, , , \C, , , \C, , S 78
79 , \C, , , \H, , , \H, , , \ H, , , \H, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \H, , , \H, , , \H, , , \H, , , \C, , , \F, , , \F, , , \F, , , \, , , \O, , , \O, , , \, , , \H, , , \H, , , \\Version=EM64L-G09RevC.01\State=2-A\HF= \S2= \S2-1=0.\S2A= \RMSD=1. 642e-09\RMSF=3.235e-07\Dipole= , , \Quadrupo le= , , , , , \pg= C01 1 X = OAc, Y = OMe 1\1\GIC-OCTOPUS\FOpt\UB3LYP\6-31G(2d,p)\C22H183O3(2)\PIOTR\23-Feb-20 14\0\\#P B3LYP/6-31G(2d,p) FOpt=tight freq(noraman) SCF=Direct #P Geom =(odistance,oangle) fcheck\\7-cf3-1-phoac-3-phome-benzotrazinyl, C1\ \0,2\C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \, , , \, , , \H, , , \C, , , \, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \H, , , \H, , , \H, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \H, , , \H, , , \H, , , \O, , , \H, , , \C, , , \O, , , \C, , , \H, , , \H, , , \H, , , \O, , , \C, , , \H, , , \H, , , \H, , , \H, , , \\Version=EM64L-G09Re vc.01\state=2-a\hf= \s2= \s2-1=0.\s2a= \rmsd= 6.357e-09\RMSF=1.065e-06\Dipole= , , \Quadru pole= , , , , , \pg =C01 [X(C22H183O3)]\\@ S 79
80 4x 1\1\GIC-OCTOPUS\FOpt\UB3LYP\6-31G(2d,p)\C21H183O2(2)\PIOTR\25-Mar-20 14\0\\#P B3LYP/6-31G(2d,p) FOpt=tight freq(noraman) SCF=Direct #P Geom =(odistance,oangle) fcheck\\7-h-1,3-(phome)-benzotrazinyl, C1\\0,2\C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \, , , \, , , \H, , , \C, , , \, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \H, , , \H, , , \H, , , \C, , , \C, , , \C, , , \C, , , \C, , , \C, , , \H, , , \H, , , \ H, , , \H, , , \O, , , \H, , , \O, , , \C, , , \H, , , \H, , , \H, , , \H, , , \C, , , \H, , , \H, , , \H, , , \\Version=EM64L-G09RevC.01\State=2-A\HF= \S2= \S2-1=0.\S2A= \RMSD=2.071e-09\RMSF=9.631e-07 \Dipole= , , \Quadrupole= , , ,5.266, , \PG=C01 S 80
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