Supporting Information. Route to benzo- and pyrido-fused 1,2,4-triazinyl radicals via N'-(het)aryl- N'-[2-nitro(het)aryl]hydrazides

Supporting Information Route to benzo- and pyrido-fused 1,2,4-triazinyl radicals via N'-(het)aryl- N'-[2-nitro(het)aryl]hydrazides Andrey A. Berezin, Georgia Zissimou, Christos P. Constantinides, Yassine Beldjoudi, Jeremy M. Rawson, Panayiotis A. Koutentis *, Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, Ontario, Canada N9B 3P4 Koutenti@ucy.ac.cy S1

Supporting Information Table of Contents Page Figures S1-S13. Solid-State and Solution EPR Spectra of New Radicals 1c-o S3-S21 Table T1. Spin Densities (ρ) Estimated from Hyperfine Coupling Constants using McConnell s Equation b NMR Spectra. 1 H and 13 C NMR Spectra for All New Compounds Figures S14-S26. Cyclic Voltammograms of Radicals 1c-o S22 S23 S78-S84 S2

Figure S1. EPR spectra of radical 1c. Solution: g = 2.0040, a N(1) /G = 7.68, a N(2) /G = 4.84, a N(4) /G = 4.90, a F /G = 0.54, ΔH pp /G = 1.79. Solution (2 nd deriv.): a N(1) /G = 7.69, a N(2) /G = 4.75, a N(4) /G = 5.00, a F /G = 0.73, ΔH pp /G = 1.90. S3

Solid-State: g = 2.0041 S4

Figure S2. EPR spectra of radical 1d. Solution: g = 2.0040, a N(1) /G = 7.81, a N(2) /G = 4.83, a N(4) /G = 5.07, ΔH pp /G = 1.80. Solid-State: g = 2.0040 S5

Figure S3. EPR spectra of radical 1e. Solution: g = 2.0040, a N(1) /G = 7.69, a N(2) /G = 4.57, a N(4) /G = 5.13, ΔH pp /G = 2.00. Solid-State: g = 2.0060 S6

Figure S4. EPR spectra of radical 1f. Solution: g = 2.0041, a N(1) /G = 7.82, a N(2) /G = 4.94, a N(4) /G = 4.95, ΔH pp /G = 2.26. Solid-State: g = 2.0042 S7

Figure S5. EPR spectra of radical 1g. Solution: g = 2.0035, a N(1) /G = 7.97, a N(2) /G = 4.23, a N(4) /G = 5.03, a F(7) /G = 3.14 ΔH pp /G = 1.43. Solution (2 nd deriv.): a N(1) /G = 7.97, a N(2) /G = 4.37, a N(4) /G = 5.36, a F(7) /G = 3.02, ΔH pp /G = 2.93. S8

Figure S6. EPR spectra of radical 1h. Solution: g = 2.0050, a N(1) /G = 8.07, a N(2) /G = 4.21, a N(4) /G = 5.36, a F(3) /G = 1.89 ΔH pp /G = 1.53. Solution (2 nd deriv.): a N(1) /G = 8.07, a N(2) /G = 4.19, a N(4) /G = 5.31, a F(3) /G = 1.26, ΔH pp /G = 2.06. S10

Figure S7. EPR spectra of radical 1i. Solution: g = 2.0042, a N(1) /G = 6.64, a N(2) /G = 4.38, a N(4) /G = 4.38, a F(3) /G = 4.39, a F(7) /G = 4.44 ΔH pp /G = 1.59. Solution (2 nd deriv.): a N(1) /G = 8.13, a N(2) /G = 2.70, a N(4) /G = 3.62, a F(3) /G = 4.02, a F(7) /G = 4.75, ΔH pp /G = 1.59. S12

Figure S8. EPR spectra of radical 1j. Solution: g = 2.0040, a N(1) /G = 7.51, a N(2) /G = 4.94, a N(4) /G = 5.13, ΔH pp /G = 2.00. Solid-State: g = 2.0046 S14

Figure S9. EPR spectra of radical 1k. Solution: g = 2.0040, a N(1) /G = 6.89, a N(2) /G = 4.95, a N(4) /G = 5.08, ΔH pp /G = 2.30. Solid-State: g = 2.0040 S15

Figure S10. EPR spectra of radical 1l. Solution: g = 2.0040, a N(1) /G = 7.12, a N(2) /G = 4.89, a N(4) /G = 5.26, ΔH pp /G = 2.49. Solid-State: g = 2.0040 S16

Figure S11. EPR spectra of radical 1m. Solution: g = 2.0040, a N(1) /G = 6.74, a N(2) /G = 4.88, a N(4) /G = 4.93, ΔH pp /G = 2.06. Solid-State: g = 2.0046 S17

Figure S12. EPR spectra of radical 1n. Solution: g = 2.0040, a N(1) /G = 6.88, a N(2) /G = 4.81, a N(4) /G = 4.81, a N(8) /G = 2.00, ΔH pp /G = 2.06. Solution (2 nd deriv.): a N(1) /G = 7.12, a N(2) /G = 4.81, a N(4) /G = 5.13, a N(8) /G = 1.94, ΔH pp /G = 2.12. S18

Figure S13. EPR spectra of radical 1o. Solution: g = 2.0040, a N(1) /G = 6.88, a N(2) /G = 4.20, a N(4) /G = 4.44, a F(7) /G = 4.38 ΔH pp /G = 1.95. Solution (2 nd deriv.): a N(1) /G = 6.88, a N(2) /G = 4.25, a N(4) /G = 4.32, a F(7) /G = 4.32, ΔH pp /G = 1.87. S20

Table T1. Spin densities (ρ) estimated from hyperfine coupling constants using McConnell s equation a Radical N1 N2 N4 1c 0.307 0.228 0.231 1c b 0.308 0.224 0.236 1d 0.312 0.228 0.239 1e 0.308 0.216 0.242 1f 0.313 0.233 0.233 1g 0.319 0.200 0.237 1g b 0.319 0.206 0.253 1h 0.323 0.199 0.253 1h b 0.323 0.198 0.250 1i 0.266 0.207 0.207 1i b 0.325 0.127 0.171 1j 0.300 0.233 0.242 1k 0.276 0.233 0.240 1l 0.285 0.231 0.248 1m 0.270 0.230 0.233 1n 0.275 0.227 0.227 1n b 0.285 0.227 0.242 1o 0.275 0.198 0.209 1o b 0.275 0.200 0.204 a a N = Q N ρ N, where a N are the hfcc in Gauss; Q N = 21.2 G (for N2 and N4) and Q N = 25 G (for N1). b Simulated second derivative EPR spectrum. S22

NMR Spectra. 1 H and 13 C NMR Spectra for All New Compounds S23

N'-(2-aminophenyl)-N'-phenylbenzohydrazide 8.20 8.151 8.10 7.9 7.855 7.841 7.838 NH 2 2.00 7.8 N NH 7.7 O 7.577 7.562 7.547 7.6 2.00 2.01 2.01 2.01 1.02 1.02 2.01 1.03 7.478 7.462 7.447 1.98 8.151 7.855 7.841 7.838 7.577 7.562 7.547 7.478 7.462 7.447 7.260 7.248 7.233 7.230 7.216 7.159 7.144 7.130 7.127 6.900 6.885 6.870 6.824 6.822 6.807 6.805 6.775 6.760 6.743 6.740 6.728 6.725 6.713 6.710 4.722 7.5 2.01 7.4 7.260 7.248 7.233 7.230 7.216 7.159 7.144 7.130 7.127 7.3 2.01 7.2 2.01 7.1 6.900 6.885 6.870 6.824 6.822 6.807 6.805 6.775 6.760 6.743 6.740 6.728 6.725 6.713 6.710 7.0 1.02 6.9 1.02 2.01 1.03 6.8 6.7 4.8 1.98 4.722 4.6 Current Data Parameters NAME Georgia Z EXPNO PROCNO 529 1 F2 - Acquisition Parameters Date_ 20131013 Time 22.45 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG TD zg30 65536 SOLVENT CDCl3 NS 16 DS 2 SWH 10330.578 Hz FIDRES 0.157632 Hz AQ RG 3.1719425 sec 128 DW 48.400 usec DE 6.50 usec TE 296.7 K D1 000000 sec TD0 1 ======== CHANNEL f1 ======== SFO1 500.0361158 MHz NUC1 1H P1 11.75 usec PLW1 15.41699982 W F2 - Processing parameters SI 65536 SF 500.0330404 MHz WDW EM SSB 0 LB GB 0 0.30 Hz PC 12 11 10 9 8 7 6 5 4 3 2 1 0

N'-(2-aminophenyl)-N'-phenylbenzohydrazide 167.390 NH 2 N NH O 147.025 145.856 129.198 129.087 128.834 132.352 132.246 130.372 129.198 129.087 128.834 127.958 127.258 120.177 118.404 116.570 113.314 Current Data Parameters NAME Georgia Z EXPNO 530 PROCNO 1 F2 - Acquisition Parameters Date_ 20131013 Time 22.48 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD SOLVENT 65536 CDCl3 NS 5120 DS 4 SWH 29761.904 Hz FIDRES 0.454131 Hz AQ 1.1010048 sec RG DW 2050 16.800 usec DE 6.50 usec TE 297.4 K CNST2 145.0000000 CNST11 00000 D1 2.00000000 sec D20 TD0 0.00689655 sec 1 165 160 167.390 155 150 145 147.025 145.856 132.352 132.246 130.372 129.198 129.087 128.834 127.958 127.258 120.177 118.404 116.570 113.314 129.2 129.0 140 128.8 135 77.254 77.000 76.746 130 125 120 115 110 ======== CHANNEL f1 ======== SFO1 125.7459782 MHz NUC1 13C P1 8.70 usec P2 17.40 usec PLW1 138.00000000 W ======== CHANNEL f2 ======== SFO2 500.0350280 MHz NUC2 1H CPDPRG[2 waltz16 PCPD2 80.00 usec PLW2 15.41699982 W PLW12 0.33258000 W 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 F2 - Processing parameters SI 32768 SF WDW 125.7334050 MHz EM SSB 0 LB Hz GB 0 PC 1.40

N'-(2-Aminophenyl)-N'-(pyridin-2-yl)picolinohydrazide (12b)

N'-(2-nitrophenyl)-N'-phenylbenzohydrazide (13a)

N'-[2-nitro-5-(trifluoromethyl)phenyl]-N'-phenylbenzohydrazide (13b)

N'-[2-nitro-5-(trifluoromethyl)phenyl]-N'-phenylbenzohydrazide 1.0 144.436 143.974 F F F 139.271 133.354 133.094 132.841 132.581 132.357 131.462 129.302 128.615 127.546 126.838 126.130 123.956 123.739 121.782 120.445 120.424 120.229 120.200 119.614 118.307 Current Data Parameters NAME Andrey EXPNO 232 PROCNO 1 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 O - N + O N HN O 0.2 0.1 0.0 120.445 120.424 120.229 120.200 120.171 120.5 120.0 F2 - Acquisition Parameters Date_ 20130420 Time 10.22 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD 65536 SOLVENT DMSO NS 1000 DS 4 SWH 29761.904 Hz FIDRES 0.454131 Hz AQ 1.1010048 sec RG 2050 DW 16.800 usec DE 6.50 usec TE 296.7 K CNST2 145.0000000 CNST11 00000 D1 2.00000000 sec D20 0.00689655 sec TD0 1 0.0-0.1-0.2-0.3 1.0 0.5 0.0 145 140 135 130 125 120 165.934 144.436 143.974 139.271 133.354 133.094 132.841 132.357 131.462 129.302 128.615 127.546 126.838 123.739 120.445 120.200 118.307 39.927 39.761 39.595 39.429 39.256 38.923 ======== CHANNEL f1 ======== SFO1 125.7459782 MHz NUC1 13C P1 8.70 usec P2 17.40 usec PLW1 138.00000000 W ======== CHANNEL f2 ======== SFO2 500.0350280 MHz NUC2 1H CPDPRG[2 waltz16 PCPD2 80.00 usec PLW2 15.41699982 W PLW12 0.33258000 W F2 - Processing parameters SI 32768 SF 125.7334723 MHz WDW EM SSB 0 LB Hz GB 0 PC 1.40 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10

4-fluoro-N'-(2-nitrophenyl)-N'-phenylbenzohydrazide

N'-(2-nitrophenyl)-N'-phenyl-2-thiophenecarbohydrazide_(13d)

N'-(2-nitrophenyl)-N'-phenyl-2-thiophenecarbohydrazide (13d)

N'-(2-nitrophenyl)-N'-phenyl-2-pyridinecarbohydrazide 8.685 8.676 8.137 8.121 8.064 8.049 8.046 8.043 8.033 8.027 7.898 7.882 7.822 7.807 7.791 7.679 7.670 7.667 7.664 7.655 7.559 7.544 7.528 7.249 7.232 7.217 6.938 6.924 6.909 6.881 6.865 0.60 0.55 0.50 N Current Data Parameters NAME Andrey EXPNO 35 PROCNO 1 0.45 0.40 0.35 0.30 0.25 0.20 0.15 O - N + O HN N O F2 - Acquisition Parameters Date_ 20111005 Time 17.07 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 65536 SOLVENT Acetone NS 16 DS 2 SWH 10330.578 Hz FIDRES 0.157632 Hz AQ 3.1719923 sec RG 144 DW 48.400 usec DE 6.50 usec TE 296.5 K D1 000000 sec 0.10 0.05 ======== CHANNEL f1 ======== NUC1 1H P1 1 usec PLW1 15.41699982 W SFO1 500.0361158 MHz 0.00 2.00 2.02 4.12 2.01 2.14 2.13 2.29 4.34 2.15 4.08 8.7 8.6 8.5 8.4 8.3 8.2 8.1 8.0 7.9 7.8 7.7 7.6 7.5 7.4 7.3 7.2 7.1 7.0 6.9 6.8 10.464 8.685 8.676 8.137 8.121 8.046 8.043 8.027 7.882 7.807 7.544 7.249 7.232 7.217 6.924 6.881 6.865 2.828 2.794 2.050 2.046 F2 - Processing parameters SI 65536 SF 500.0330363 MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC 0.5 0.0 1.05 2.00 4.12 2.294.34 4.08 12 11 10 9 8 7 6 5 4 3 2 1 0

N'-(2-Nitrophenyl)-N'-phenylpicolinohydrazide (13e)

N'-(2-Nitrophenyl)-N'-phenylacetohydrazide (13f)

Current Data Parameters NAME Andrey EXPNO 274 PROCNO 1 F F F N N + 10.777 10.227 8.160 8.144 8.071 8.054 7.902 7.768 7.751 7.686 7.659 7.642 7.338 7.322 7.304 7.288 7.273 7.125 7.110 7.049 7.034 7.019 6.948 0.35 0.30 0.25 0.20 0.15 0.10 O - NH O O CH 3 F2 - Acquisition Parameters Date_ 20130516 Time 17.27 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 65536 SOLVENT DMSO NS 16 DS 2 SWH 10330.578 Hz FIDRES 0.157632 Hz AQ 3.1719425 sec RG 80.6 DW 48.400 usec DE 6.50 usec TE 295.6 K D1 000000 sec TD0 1 0.05 0.00 0.08 1.01 0.09 0.09 1.04 2.12 1.042.21 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 10.777 10.227 8.144 8.071 8.054 7.686 7.659 7.642 7.322 7.304 7.288 7.273 7.049 7.034 6.948 6.931 3.343 3.320 2.500 2.010 1.925 ======== CHANNEL f1 ======== SFO1 500.0361158 MHz NUC1 1H P1 11.75 usec PLW1 15.41699982 W F2 - Processing parameters SI 65536 SF 500.0330323 MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC 1.0 0.5 0.0 0.08 1.01 1.04 2.12 2.21 3.09 12 11 10 9 8 7 6 5 4 3 2 1

174.172 169.166 145.688 144.489 144.279 139.309 139.085 133.414 133.162 132.902 132.641 129.434 129.196 126.956 126.754 126.104 124.305 123.929 123.200 121.755 121.083 121.054 120.809 120.780 118.186 117.421 1.0 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 0.0-0.1-0.2-0.3 F F F O N + O - N NH CH 3 O 0.20 0.15 0.10 0.05 0.00-0.05 126.104 124.305 175 170 165 160 155 150 145 140 135 130 125 120 115 123.929 123.200 121.755 121.083 121.054 120.809 120.780 126 125 124 123 122 121 120 119.581 Current Data Parameters NAME Andrey EXPNO 275 PROCNO 1 F2 - Acquisition Parameters Date_ 20130516 Time 17.34 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD 65536 SOLVENT DMSO NS 600 DS 4 SWH 29761.904 Hz FIDRES 0.454131 Hz AQ 1.1010548 sec RG 1820 DW 16.800 usec DE 6.50 usec TE 296.5 K CNST2 145.0000000 CNST11 00000 D1 2.00000000 sec d20 0.00689655 sec DELTA 0.00001108 sec TD0 1 NUC1 13C P1 8.70 usec p2 17.40 usec PLW1 138.00000000 W SFO1 125.7459782 MHz CPDPRG2 NUC2 1H PLW2 15.41699982 W PLW12 0.33258000 W SFO2 500.0350280 MHz 1.0 0.5 174.172 169.166 145.688 144.489 144.279 139.085 133.162 132.902 129.434 129.196 126.956 126.754 123.929 123.200 121.755 121.054 120.780 118.186 117.421 39.930 39.850 39.763 39.684 39.590 39.424 39.258 39.092 20.093 19.313 F2 - Processing parameters SI 32768 SF 125.7334739 MHz WDW EM SSB 0 LB Hz GB 0 PC 1.40 0.0 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0

2,2,2-Trifluoro-N'-(2-nitrophenyl)-N'-phenylacetohydrazide (13h)

2,2,2-trifluoro-N'-[2-nitro-5-(trifluoromethyl)phenyl]-N'-phenylacetohydrazide 8.167 8.138 F F F 7.804 7.774 7.717 7.379 7.353 7.326 7.151 7.126 7.102 6.985 6.959 Current Data Parameters NAME Andrey EXPNO 708 PROCNO 708 0.04 0.03 0.02 O - N + O N HN F F O F F2 - Acquisition Parameters Date_ 20130312 Time 21.43 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 65536 SOLVENT DMSO NS 16 DS 2 SWH 6172.839 Hz FIDRES 0.094190 Hz AQ 5.3084660 sec RG 287.4 DW 80 usec DE 9.00 usec TE 297.2 K D1 000000 sec TD0 1 0.01 ======== CHANNEL f1 ======== NUC1 1H P1 9.00 usec PL1 0.00 db SFO1 300.1318534 MHz 0.00 0.04 0.03 0.02 0.02 0.02 0.04 0.02 0.04 8.3 8.2 8.1 8.0 7.9 7.8 7.7 7.6 7.5 7.4 7.3 7.2 7.1 7.0 6.9 12.589 8.167 8.138 7.804 7.774 7.717 7.379 7.353 7.326 7.151 7.126 7.102 6.985 6.959 3.338 2.506 2.494 F1 - Acquisition parameters ND0 2 TD 256 SFO1 300.1314 MHz FIDRES 12.056327 Hz SW 10.284 ppm FnMODE undefined F2 - Processing parameters SI 32768 SF 300.1300011 MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC 0.02 0.01 0.00 0.02 0.02 0.02 0.04 0.04 13 12 11 10 9 8 7 6 5 4 3 2 1 0 F1 - Processing parameters SI 1024 MC2 QF SF 300.1300000 MHz WDW SINE SSB 0 LB 0.30 Hz GB 0.1

2,2,2-trifluoro-N'-[2-nitro-5-(trifluoromethyl)phenyl]-N'-phenylacetohydrazide 1.0 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 0.0-0.1 156.550 156.063 155.576 155.088 F O - F N + F O N HN F F O F 145.240 143.946 0.1 0.0 122.490 122.446 122.395 137.793 134.069 133.640 133.203 132.767 121.253 121.202 121.159 121.108 121.057 120.904 122 121 129.487 128.141 126.948 124.526 124.257 122.490 122.446 121.159 121.108 121.057 120.904 118.184 117.428 117.282 113.602 109.784 Current Data Parameters NAME Andrey EXPNO 710 PROCNO 710 F2 - Acquisition Parameters Date_ 20130312 Time 22.05 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD 65536 SOLVENT DMSO NS 10000 DS 4 SWH 17985.611 Hz FIDRES 0.274439 Hz AQ 1.8219508 sec RG 16384 DW 27.800 usec DE 6.00 usec TE 297.2 K CNST2 145.0000000 CNST11 00000 D1 2.00000000 sec d20 0.00689655 sec DELTA 0.00000908 sec TD0 1 ======== CHANNEL f1 ======== NUC1 13C P1 7.13 usec p2 14.26 usec PL1-2.00 db SFO1 75.4752953 MHz -0.2-0.3 1.0 0.5 0.0 155 150 145 140 135 130 125 120 115 110 156.550 156.063 155.576 155.088 145.240 143.946 137.793 133.640 133.203 132.767 129.487 126.948 124.526 124.257 122.490 121.159 121.108 118.184 117.428 113.602 109.784 40.259 39.982 39.706 39.430 39.153 38.870 38.593 ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 110.00 usec PL2 0.00 db PL12 22.00 db SFO2 300.1312005 MHz F2 - Processing parameters SI 32768 SF 75.4677888 MHz WDW EM SSB 0 LB Hz GB 0 PC 1.40 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0

N'-(4-Cyanophenyl)-N'-(2-nitrophenyl)benzohydrazide (13j)

N'-(4-Cyanophenyl)-N'-(2-nitrophenyl)thiophene-2-carbohydrazide (13k)

N'-(2-Nitrophenyl)-N'-(pyridin-2-yl)benzohydrazide N N Current Data Parameters NAME Georgia Z EXPNO 535 PROCNO 1 N + O O - NH O F2 - Acquisition Parameters Date_ 20131016 Time 14.59 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 65536 SOLVENT NS CDCl3 16 DS 2 SWH 10330.578 Hz FIDRES 0.157632 Hz AQ 3.1719425 sec RG 71.8 DW DE 48.400 usec 6.50 usec TE 296.2 K D1 000000 sec TD0 1.15 8.10 1.02 8.05 8.00 7.95 7.90 2.02 7.85 7.80 7.75 1.02 2.02 1.03 2.06 3.06 1.03 8.086 8.084 8.076 8.074 8.068 8.065 8.052 8.049 8.020 8.018 8.004 8.002 7.888 7.874 7.871 7.736 7.733 7.721 7.718 7.705 7.702 7.584 7.569 7.557 7.554 7.543 7.541 7.538 7.527 7.523 7.508 7.505 7.488 7.471 7.456 6.849 6.832 6.804 6.793 6.790 6.780 7.70 7.65 8.877 8.086 8.084 8.076 8.074 8.068 8.065 8.052 8.049 8.020 8.018 8.004 8.002 7.888 7.874 7.871 7.736 7.733 7.721 7.718 7.705 7.702 7.584 7.569 7.557 7.554 7.543 7.541 7.538 7.527 7.523 7.508 7.505 7.488 7.471 7.456 7.260 6.849 6.832 6.804 6.793 6.790 6.780 2.161 7.60 2.06 7.55 7.50 3.06 7.45 6.85 6.80 ======== CHANNEL f1 ======== SFO1 500.0361158 MHz 6.75NUC1 1H P1 11.75 usec PLW1 15.41699982 W F2 - Processing parameters SI 65536 SF 500.0330401 MHz WDW EM SSB LB 0 0.30 Hz GB PC 0 12 11 10 9 8 7 6 5 4 3 2 1 0

N'-(2-nitrophenyl)-N'-(pyridin-2-yl)benzohydrazide 166.76 156.94 147.78 146.12 138.13 137.08 134.85 132.58 132.56 131.86 128.84 128.43 127.39 125.58 116.44 107.19 132.58 132.56 77.25 77.00 76.75 EXPNO 544 PROCNO 1 F2 - Acquisition Parameters Date_ 20131017 Time 9.29 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD 65536 SOLVENT CDCl3 NS 105 DS 4 SWH 29761.904 Hz FIDRES 0.454131 Hz AQ 1.1010048 sec RG 2050 DW 16.800 usec DE 6.50 usec TE 296.7 K CNST2 145.0000000 CNST11 00000 D1 2.00000000 sec D20 0.00689655 sec TD0 1 132.65 132.55 132.45 ======== CHANNEL f1 ======== SFO1 125.7459782 MHz NUC1 13C P1 8.70 usec P2 17.40 usec PLW1 138.00000000 W 170 165 160 155 150 166.76 145 140 135 130 125 156.94 147.78 146.12 138.13 137.08 134.85 132.58 132.56 131.86 128.84 128.43 127.39 125.58 116.44 107.19 120 115 77.25 77.00 76.75 110 105 100 95 90 85 80 75 ======== CHANNEL f2 ======== SFO2 500.0350280 MHz NUC2 1H CPDPRG[2 waltz16 PCPD2 80.00 usec PLW2 15.41699982 W PLW12 0.33258000 W F2 - Processing parameters SI 32768 SF 125.7334143 MHz WDW EM SSB 0 LB Hz GB 0 PC 1.40 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0-10

N'-(2-Nitrophenyl)-N'-(pyridin-2-yl)picolinohydrazide (13m)

N'-[2-Nitro-5-(trifluoromethyl)phenyl]-N'-(pyridin-2-yl)picolinohydrazide (13n)

N'-(3-Nitropyridin-2-yl)-N'-phenylbenzohydrazide 8.582 8.454 8.451 8.444 8.442 8.142 8.139 8.126 8.123 7.822 7.807 7.582 7.567 7.552 7.483 7.467 7.452 7.377 7.362 7.346 7.335 7.320 7.260 7.219 7.204 7.190 7.066 7.056 7.050 7.040 Current Data Parameters NAME Georgia Z EXPNO 527 PROCNO 1 N N + O O - N NH O F2 - Acquisition Parameters Date_ 20131013 Time 17.17 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 65536 SOLVENT CDCl3 NS 16 DS 2 SWH 10330.578 Hz FIDRES 0.157632 Hz AQ 3.1719425 sec RG 128 DW 48.400 usec DE 6.50 usec TE 297.8 K D1 000000 sec TD0 1 ======== CHANNEL f1 ======== SFO1 500.0361158 MHz NUC1 1H P1 11.75 usec PLW1 15.41699982 W 8.6 8.5 8.4 8.3 8.2 8.1 8.582 8.454 8.451 8.444 8.442 8.142 8.139 8.126 8.123 7.822 7.807 7.582 7.567 7.552 7.483 7.467 7.452 7.377 7.362 7.346 7.335 7.320 7.260 7.219 7.204 7.190 7.066 7.056 7.050 7.040 8.0 7.9 2.00 7.8 7.7 7.6 7.5 2.01 7.4 6.05 1.01 7.3 7.2 7.1 1.02 2.00 2.01 6.05 1.01 1.02 1.625 0.001 F2 - Processing parameters SI 65536 7.0 SF WDW 500.0330407 MHz EM SSB 0 LB 0.30 Hz GB 0 PC 12 11 10 9 8 7 6 5 4 3 2 1 0

N'-(3-nitropyridin-2-yl)-N'-phenylbenzohydrazide 135.130 135.007 N N + O O - N NH O 132.618 131.475 129.287 128.894 128.316 127.364 126.039 Current Data Parameters NAME Georgia Z EXPNO 528 PROCNO 1 F2 - Acquisition Parameters Date_ 20131013 Time 17.26 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD 65536 SOLVENT CDCl3 NS 5120 DS 4 SWH 29761.904 Hz FIDRES 0.454131 Hz AQ 1.1010048 sec RG 2050 DW 16.800 usec DE 6.50 usec TE 298.8 K CNST2 145.0000000 CNST11 00000 D1 2.00000000 sec D20 0.00689655 sec TD0 1 35.5 135.0 134.5 134.0 166.444 133.5 133.0 151.887 150.333 132.5 132.0 131.5 131.0 143.563 135.130 135.007 132.618 131.475 129.287 128.894 128.316 127.364 126.039 122.133 117.540 130.5 130.0 129.5 77.255 77.000 76.746 129.0 128.5 128.0 127.5 127.0 126.5 126.0 125.5 ======== CHANNEL f1 ======== SFO1 125.7459782 MHz NUC1 13C P1 8.70 usec P2 17.40 usec PLW1 138.00000000 W ======== CHANNEL f2 ======== SFO2 500.0350280 MHz NUC2 1H CPDPRG[2 waltz16 PCPD2 80.00 usec PLW2 15.41699982 W PLW12 0.33258000 W F2 - Processing parameters SI 32768 SF 125.7334087 MHz WDW EM SSB 0 LB Hz GB 0 PC 1.40 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0

N'-(3-nitropyridin-2-yl)-N'-(pyridin-2-yl)picolinohydrazide 8.743 8.734 8.561 8.558 8.552 8.549 8.383 8.380 8.367 8.364 8.066 8.063 8.050 8.047 8.035 8.025 8.024 7.998 7.995 7.988 7.986 7.763 7.759 7.748 7.745 7.742 7.731 7.727 7.704 7.699 7.694 7.691 7.689 7.686 7.682 7.676 7.348 7.338 7.332 7.322 7.145 7.129 7.007 6.997 6.993 6.983 N O 8.8 N 8.7 N N + O NH O - 8.6 1.02 N 8.5 8.4 8.3 8.2 8.1 1.93 11.710 8.743 8.734 8.561 8.558 8.552 8.549 8.383 8.380 8.367 8.364 8.066 8.063 8.050 8.047 8.035 8.025 8.024 7.998 7.995 7.988 7.986 7.763 7.759 7.748 7.745 7.742 7.731 7.727 7.704 7.699 7.694 7.691 7.689 7.686 7.682 7.676 7.348 7.338 7.332 7.322 7.145 7.129 7.007 6.997 6.993 6.983 2.504 2.500 2.497 1.06 8.0 7.9 7.8 1.03 1.04 7.7 7.6 7.5 7.4 0.86 7.3 7.2 0.90 7.1 1.03 7.0 Current Data Parameters NAME Georgia Z EXPNO PROCNO 580 1 F2 - Acquisition Parameters Date_ 20131101 Time 6.19 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 65536 SOLVENT DMSO NS 16 DS 2 SWH 10330.578 Hz FIDRES AQ 0.157632 Hz 3.1719425 sec RG 32 DW 48.400 usec DE 6.50 usec TE 298.9 K D1 000000 sec TD0 6.9 1 ======== CHANNEL f1 ======== SFO1 500.0361158 MHz NUC1 1H P1 11.75 usec PLW1 15.41699982 W 0.78 1.02 1.93 1.06 1.03 1.04 0.86 0.90 1.03 F2 - Processing parameters SI SF 65536 500.0330313 MHz WDW SSB 0 EM LB GB 0 0.30 Hz PC 12 11 10 9 8 7 6 5 4 3 2 1 0

N'-(3-nitropyridin-2-yl)-N'-(pyridin-2-yl)picolinohydrazide 163.764 155.378 151.946 149.087 148.941 146.426 145.751 138.886 138.012 137.577 134.076 127.412 122.763 119.511 118.883 112.009 Current Data Parameters NAME Georgia Z EXPNO 581 PROCNO 1 N N N + O N NH O - O N F2 - Acquisition Parameters Date_ 20131101 Time 9.23 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD SOLVENT 65536 DMSO NS 3540 DS 4 SWH 29761.904 Hz FIDRES 0.454131 Hz AQ 1.1010048 sec RG DW 2050 16.800 usec DE 6.50 usec TE 299.8 K CNST2 145.0000000 CNST11 00000 D1 2.00000000 sec D20 TD0 0.00689655 sec 1 ======== CHANNEL f1 ======== SFO1 125.7459782 MHz NUC1 13C P1 8.70 usec P2 17.40 usec PLW1 138.00000000 W 165 160 163.764 155 150 155.378 151.946 149.087 148.941 146.426 145.751 138.886 138.012 137.577 134.076 145 127.412 122.763 119.511 118.883 112.009 140 135 130 125 120 39.932 39.764 39.597 39.430 39.263 39.095 38.927 115 110 ======== CHANNEL f2 ======== SFO2 500.0350280 MHz NUC2 1H CPDPRG[2 waltz16 PCPD2 80.00 usec PLW2 15.41699982 W PLW12 0.33258000 W 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 F2 - Processing parameters SI 32768 SF WDW 125.7334524 MHz EM SSB 0 LB Hz GB 0 PC 1.40

10.399 7.827 7.811 7.653 7.638 7.622 7.439 7.422 7.278 7.263 7.249 7.235 7.220 6.955 6.941 6.927 6.833 6.817 0.07 1.975 1.840 1.665 0.06 N 0.25 Current Data Parameters NAME Andrey EXPNO 183 PROCNO 1 0.05 0.04 0.03 0.02 O - N + O HN O 0.20 0.15 0.10 0.05 F2 - Acquisition Parameters Date_ 20130226 Time 18.14 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 65536 SOLVENT DMSO NS 16 DS 2 SWH 10330.578 Hz FIDRES 0.157632 Hz AQ 3.1719923 sec RG 114 DW 48.400 usec DE 6.50 usec TE 295.1 K D1 000000 sec TD0 1 0.01 0.00 0.99 1.03 1.01 3.06 2.02 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 10.399 0.00 3.05 7.827 7.811 7.638 7.622 7.439 7.422 7.263 7.249 7.235 7.220 6.941 6.833 6.817 6.19 6.24 2.0 1.9 1.8 1.7 1.6 3.343 2.499 1.975 1.840 1.665 ======== CHANNEL f1 ======== NUC1 1H P1 11.75 usec PLW1 15.41699982 W SFO1 500.0361158 MHz F2 - Processing parameters SI 65536 SF 500.0330318 MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC 0.2 0.1 0.0 1.03 3.06 2.02 3.056.24 11 10 9 8 7 6 5 4 3 2 1 0

0.60 0.55 0.50 0.45 0.40 0.35 0.30 0.25 0.20 0.15 0.10 0.05 0.00-0.05-0.10-0.15-0.20 0.5 0.0 175.738 O - N + O 175.738 N HN O 1 0-1 145.629 142.400 138.636 39.762 39.596 39.430 39.264 39.090 DMSO-d6 38.021 35.883 133.724 128.826 125.142 124.477 124.029 121.913 116.646 0.0-0.5 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 145.629 39.928 142.400 39.762 40 35 30 39.596 138.636 133.724 40.0 39.5 39.0 128.826 DMSO-d6 125.142 124.477 124.029 39.928 39.762 39.596 39.264 39.090 38.924 38.021 35.883 27.424 121.913 116.646 Current Data Parameters NAME Andrey EXPNO 184 PROCNO 1 F2 - Acquisition Parameters Date_ 20130226 Time 18.39 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG jmod TD 65536 SOLVENT DMSO NS 284 DS 4 SWH 29761.904 Hz FIDRES 0.454131 Hz AQ 1.1010548 sec RG 1820 DW 16.800 usec DE 6.50 usec TE 296.1 K CNST2 145.0000000 CNST11 00000 D1 2.00000000 sec D20 0.00689655 sec TD0 1 ======== CHANNEL f1 ======== NUC1 13C P1 8.38 usec P2 16.76 usec PLW1 138.00000000 W SFO1 125.7459782 MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD2 80.00 usec 175 170 165 160 155 150 145 140 135 130 125 120 115 PLW2 15.41699982 W PLW12 0.33258000 W SFO2 500.0350280 MHz 39.430 39.264 DMSO-d6 27.424 39.090 38.924 F2 - Processing parameters SI 32768 SF 125.7334742 MHz WDW EM SSB 0 LB Hz GB 0 PC 1.40

N'-(4-Cyanophenyl)benzohydrazide 7.914 7.900 N 7.610 7.595 7.581 7.568 7.551 7.530 7.514 7.499 6.836 6.818 7.610 7.595 7.581 7.568 7.551 7.530 7.514 7.499 Current Data Parameters NAME Georgia Z EXPNO 551 PROCNO 1 HN NH O 7.62 1.09 7.60 7.58 2.00 7.56 7.54 2.07 7.52 7.50 7.48 F2 - Acquisition Parameters Date_ 20131019 Time 21.42 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD 65536 SOLVENT DMSO NS 16 DS 2 SWH 10330.578 Hz FIDRES 0.157632 Hz AQ 3.1719425 sec RG 32 DW 48.400 usec DE 6.50 usec TE 298.3 K D1 000000 sec TD0 1 ======== CHANNEL f1 ======== SFO1 500.0361158 MHz NUC1 1H P1 11.75 usec PLW1 15.41699982 W 8.0 2.00 7.9 10.525 7.8 7.7 1.09 7.6 0.80 0.85 2.00 1.09 2.00 2.07 1.91 2.00 2.07 7.5 8.775 7.914 7.900 7.610 7.595 7.581 7.568 7.551 7.530 7.514 7.499 6.836 6.818 7.4 7.3 7.2 7.1 7.0 2.503 2.500 2.497 6.9 1.91 6.8 6.7 F2 - Processing parameters SI 65536 SF 500.0330320 MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC 12 11 10 9 8 7 6 5 4 3 2 1 0

N'-(4-Cyanophenyl)benzohydrazide 166.575 153.101 N HN NH O 133.560 132.550 132.087 128.700 127.478 120.171 111.931 99.096 Current Data Parameters NAME Georgia Z EXPNO 552 PROCNO 1 F2 - Acquisition Parameters Date_ 20131019 Time 23.30 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG TD jmod 65536 SOLVENT DMSO NS 2048 DS 4 SWH 29761.904 Hz FIDRES 0.454131 Hz AQ 1.1010048 sec RG DW 2050 16.800 usec DE 6.50 usec TE 299.2 K CNST2 145.0000000 CNST11 00000 D1 2.00000000 sec D20 TD0 0.00689655 sec 1 170 165 160 166.575 155 153.101 150 145 133.560 132.550 132.087 128.700 127.478 120.171 140 111.931 135 99.096 130 125 120 115 110 39.933 39.765 39.598 39.431 39.263 39.096 38.929 105 100 ======== CHANNEL f1 ======== SFO1 125.7459782 MHz NUC1 13C P1 8.70 usec P2 17.40 usec PLW1 138.00000000 W ======== CHANNEL f2 ======== SFO2 500.0350280 MHz NUC2 1H CPDPRG[2 waltz16 PCPD2 80.00 usec PLW2 15.41699982 W PLW12 0.33258000 W 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 F2 - Processing parameters SI SF 32768 125.7334508 MHz WDW SSB 0 EM LB Hz GB PC 0 1.40

N'-(4-Cyanophenyl)thiophene-2-carbohydrazide 7.887 7.882 7.850 7.840 7.570 7.553 7.216 7.207 7.199 N 6.813 6.796 C urrent Data Parameters NA ME Georgia Z EXPNO 573 PRO C NO 1 HN S NH O F2 - A cquisition Parameters Date_ 20131028 Time 13.12 INSTRUM spect PRO BHD 5 mm PA BBO BB- PULPRO G zg30 TD 65536 SO LV ENT DMSO NS 20 DS 2 SWH 10330.578 Hz FIDRES 0.157632 Hz A Q 3.1719425 sec RG 32 DW 48.400 usec DE 6.50 usec TE 298.1 K D1 000000 sec TD0 1 1.08 2.00 2.00 ======== C HA NNEL f1 ======== SFO 1 500.0361158 MHz NUC 1 1H P1 11.75 usec PLW1 15.41699982 W 7.9 7.8 0.88 0.88 1.08 2.00 2.00 10.552 7.7 7.6 7.5 8.791 7.887 7.882 7.850 7.840 7.570 7.553 7.216 7.207 7.199 6.813 6.796 7.4 7.3 7.2 7.1 7.0 2.500 6.9 6.8 F2 - Processing parameters SI 65536 SF 500.0330320 MHz WDW EM SSB 0 LB 0.30 Hz GB 0 PC 12 11 10 9 8 7 6 5 4 3 2 1 0

N'-(4-Cyanophenyl)thiophene-2-carbohydrazide 161.461 153.009 N HN NH O S 137.065 133.599 131.889 129.140 128.340 120.128 111.898 99.227 Current Data Parameters NAME Georgia Z EXPNO 572 PROCNO 1 F2 - Acquisition Parameters Date_ 20131028 Time INSTRUM 13.15 spect PROBHD 5 mm PABBO BB- PULPROG jmod TD 65536 SOLVENT DMSO NS 256 DS SWH 4 29761.904 Hz FIDRES 0.454131 Hz AQ 1.1010048 sec RG 2050 DW 16.800 usec DE 6.50 usec TE 298.3 K CNST2 CNST11 145.0000000 00000 D1 2.00000000 sec D20 0.00689655 sec TD0 1 165 160 155 161.461 150 153.009 145 140 137.065 133.599 131.889 129.140 128.340 120.128 135 111.898 99.227 130 125 120 115 110 39.932 39.765 39.598 39.430 39.263 39.095 38.927 105 100 ======== CHANNEL f1 ======== SFO1 125.7459782 MHz NUC1 13C P1 8.70 usec P2 17.40 usec PLW1 138.00000000 W ======== CHANNEL f2 ======== SFO2 500.0350280 MHz NUC2 1H CPDPRG[2 waltz16 PCPD2 80.00 usec PLW2 15.41699982 W PLW12 0.33258000 W 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 F2 - Processing parameters SI 32768 SF 125.7334505 MHz WDW EM SSB 0 LB Hz GB 0 PC 1.40

1,3-Di(2-pyrid-2-yl)-1,4-dihydro-1,2,4-benzotriazine (23b)

1,3-Di(pyrid-2-yl)-7-(trifluoromethyl)-1,4-dihydro-1,2,4-benzotriazine (23c)

1,3-Di(pyrid-2-yl)-1,4-dihydro-1,2,4-pyridotriazine 8.53 8.52 8.49 8.49 8.48 8.48 8.18 8.17 7.76 7.76 7.74 7.74 7.73 7.72 7.72 7.71 7.69 7.69 7.66 7.65 7.65 7.64 7.63 7.61 7.35 7.35 7.34 7.34 7.34 7.33 7.26 7.04 7.03 7.03 7.02 6.68 6.68 6.67 6.66 6.65 6.64 6.64 6.63 8.6 8.6 2.00 2.00 8.5 8.53 8.52 8.51 8.51 8.50 8.50 8.5 8.4 8.4 8.3 8.3 8.2 8.2 8.20 8.18 8.1 8.1 8.0 8.0 7.9 7.9 7.8 7.8 2.20 3.00 7.7 7.7 2.00 1.98 7.6 7.6 7.5 7.5 7.4 7.4 8.53 8.52 8.51 8.51 8.50 8.50 8.20 8.18 7.76 7.76 7.74 7.74 7.73 7.73 7.72 7.72 7.71 7.70 7.69 7.69 7.65 7.65 7.64 7.64 7.63 7.36 7.35 7.35 7.34 7.34 7.34 7.33 7.33 7.26 7.05 7.04 7.04 7.03 7.03 7.03 7.02 7.02 6.68 6.68 6.67 6.66 6.65 6.64 6.64 6.63 1.42 7.3 7.76 7.76 7.74 7.74 7.73 7.73 7.72 7.72 7.71 7.70 7.69 7.69 7.65 7.65 7.64 7.64 7.63 7.36 7.35 7.35 7.34 7.34 7.34 7.33 7.33 7.26 7.3 7.2 7.2 7.1 7.1 7.0 7.05 7.04 7.04 7.03 7.03 7.03 7.02 7.02 7.0 6.9 6.9 6.8 6.8 6.7 6.68 6.68 6.67 6.66 6.65 6.64 6.64 6.63 6.7 6.6 6.6 6.5 Current Data Parameters NAME Georgia Z EXPNO 560 PROCNO 1 F2 - Acquisition Parameters Date_ 20131024 Time 20.42 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG zg30 TD SOLVENT 65536 CDCl3 NS 28 DS 2 SWH 10330.578 Hz FIDRES 0.157632 Hz AQ 3.1719425 sec RG 71.8 DW 48.400 usec DE 6.50 usec TE 297.9 K D1 000000 sec TD0 1 6.5 ======== CHANNEL f1 ======== SFO1 500.0361158 MHz NUC1 1H P1 11.75 usec PLW1 15.41699982 W 12 11 10 9 2.00 8 3.00 1.98 7 6 5 4 3 2 1 0 F2 - Processing parameters SI SF 65536 500.0330400 MHz WDW SSB 0 EM LB 0.30 Hz GB 0 PC

1,3-Di(pyrid-2-yl)-1,4-dihydro-1,2,4-pyridotriazine N 154.134 N NH N N N 147.844 147.802 147.151 145.3 145.243 145.243 145.171 145.171 145.1 141.350 137.406 136.613 119.295 119.4 119.146 119.0 128.268 124.880 121.021 119.295 119.146 118.747 116.276 Current Data Parameters NAME Georgia Z EXPNO 561 PROCNO 1 F2 - Acquisition Parameters Date_ 20131024 Time 21.38 INSTRUM spect PROBHD 5 mm PABBO BB- PULPROG TD jmod 65536 SOLVENT CDCl3 NS 1024 DS 4 SWH 29761.904 Hz FIDRES 0.454131 Hz AQ RG 1.1010048 sec 2050 DW 16.800 usec DE 6.50 usec TE 299.2 K CNST2 145.0000000 CNST11 00000 D1 2.00000000 sec D20 TD0 0.00689655 sec 1 155 150 145 140 154.134 147.844 147.802 147.151 145.243 145.171 141.350 137.406 136.613 128.268 124.880 121.021 119.295 119.146 118.747 116.276 135 77.253 77.000 76.745 130 125 120 ======== CHANNEL f1 ======== SFO1 125.7459782 MHz NUC1 13C P1 8.70 usec P2 17.40 usec PLW1 138.00000000 W ======== CHANNEL f2 ======== SFO2 500.0350280 MHz NUC2 1H CPDPRG[2 waltz16 PCPD2 80.00 usec PLW2 15.41699982 W PLW12 0.33258000 W 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 F2 - Processing parameters SI SF 32768 125.7334142 MHz WDW SSB 0 EM LB Hz GB 0 PC 1.40

1,3-Di(pyrid-2-yl)-1,2,4-benzotriazin-7(1H)-one (24)

Figure S14. Cyclic voltammogram for radical 1c. Figure S15. Cyclic voltammogram for radical 1d.

Figure S16. Cyclic voltammogram for radical 1e. Figure S17. Cyclic voltammogram for radical 1f.

Figure S18. Cyclic voltammogram for radical 1g. Figure S19. Cyclic voltammogram for radical 1h.

Figure S20. Cyclic voltammogram for radical 1i. Figure S21. Cyclic voltammogram for radical 1j.

Figure S22. Cyclic voltammogram for radical 1k. Figure S23. Cyclic voltammogram for radical 1l.

Figure S24. Cyclic voltammogram for radical 1m. Figure S25. Cyclic voltammogram for radical 1n.

Figure S26. Cyclic voltammogram for radical 1o.