Electronic Supporting Information. Thermal conversion of a pyridine-bridged bisdithiazolyl radical to a zwitterionic bisdithiazolopyridone
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- Αντώνης Γεννάδιος
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1 Electronic Supporting Information Thermal conversion of a pyridine-bridged bisdithiazolyl radical to a zwitterionic bisdithiazolopyridone Stephen M. Winter, Ryan J. Roberts, Aaron Mailman, Kristina Cvrkalj, Abdeljalil Assoud and Richard T. Oakley* Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1 oakley@uwaterloo.ca Contents Section S1 Synthetic Procedures Page S2 Section S2 Gaussian 09 Archive Files Page S6 Section S3 EPR spectra and hyperfine coupling constants Page S10 Page S1
2 Section S1 Synthetic Procedures and Instrumental Methods. General methods and procedures The solvents acetonitrile (MeCN), dichloroethane (DCE), dichloromethane (DCM), methanol, isopropanol and diethyl ether were of at least reagent grade. MeCN was dried by distillation from P 2 O 5 and/or CaH 2, methanol by distillation from magnesium turnings, and both DCE and DCM by distillation from P 2 O 5. All reactions were performed under an atmosphere of dry nitrogen. Melting points are uncorrected. Fractional sublimations were performed in an ATS series 3210 three-zone tube furnace, mounted horizontally, and linked to a series 1400 temperature control system. Infrared spectra (Nujol mulls, KBr optics) were recorded on a Nicolet Avatar FTIR spectrometer at 2 cm -1 resolution. 1 H spectra were run on a Bruker Avance 300 MHz NMR spectrometer and low resolution Electro-Spray Ionization (ESI) mass spectra were run on a Micromass Q-TOF Ultima Global LC/MS/MS system. Elemental analyses were performed by MHW Laboratories, Phoenix, AZ Preparation of 4-methoxy-2,6-difluoropyridine 6 A solution of 2,4,6-trifluoropyridine (13.3 g, 0.10 mol) in 20 ml anhydrous methanol was added dropwise to a solution of sodium methoxide prepared by dissolving freshly cut sodium (2.30 g, 0.10 mol) in 100 ml methanol. The solution was stirred under N 2 for 1 h, and the solvent removed by rotary evaporation to leave a white paste. Diethyl ether (200 ml) was added, and the precipitate of sodium fluoride (3.9 g, mol) was filtered off. The solvent was evaporated to leave a colorless oil which was distilled to give 4- methoxy-2,6-difluoropyridine 6 (10.1 g, mol, 70 %) as a colorless oil, bp 70-72EC /10 Torr. 1 H NMR (δ, CDCl 3 ): 6.28 (s, 2H, aromatic), 3.87 (s, 3H, OMe). Anal. Calcd for C 6 H 5 F 2 NO: C, 49.66; H, 3.47; N, 9.65 %. Found: C, 48.79; H, 3.68; N, 9.77 %. Preparation of N-methyl-4-methoxy-2,6-difluoropyridinium Triflate 7 A solution of 4-methoxy- 2,6-difluoropyridine (5.00 g, 34.5 mmol) and methyl triflate (7.35 g, 44.8 mmol) in 30 ml DCE was left to stir under N 2 for 16 h. Diethyl ether (100 ml) was added and the resulting white precipitate of N-methyl-4-methoxy-2,6-difluoropyridinium triflate was filtered off, washed with 2 50 ml ether and dried in vacuo. Yield 10.0 g, 32.4 mmol, 94 %. Recrystallization from DCE/MeCN Page S2
3 afforded colorless needles, mp EC. 1 H NMR (δ, CD 3 CN): 7.17 (d, 2H, J = 4.8Hz, aromatic), 4.11 (s, 3H, NMe), 3.84 (t, 3H, J = 2.7Hz, OMe). Anal. Calcd for C 8 H 8 F 5 NO 4 S: C, 31.07; H, 2.61; N, 4.53 %. Found: C, 31.21; H, 2.89; N, 4.72 %. Preparation of N-methyl-4-methoxy-2,6-diaminopyridinium Triflate 8 Ammonia gas was bubbled into a solution of N-methyl-4-methoxy-2,6-difluoropyridinium triflate 7 (10.0 g, 32.4 mmol) in 120 ml anhydrous MeCN for 15 min. The vessel (a glass bomb) was then sealed and heated at 50 EC for 16 h. The vessel was cooled to room temperature, opened to vent, and the vessel reheated to 100 EC to discharge excess ammonia. The reaction mixture was filtered to remove NH 4 F (2.3 g), and the solvent was removed from the filtrate to afford N-methyl-4-methoxy-2,6-diaminopyridinium triflate 8 as a white solid that was recrystallized from isopropanol, mp EC. Yield 8.3 g (27.3 mmol, 84%). 1 H NMR (δ, CD 3 CN): 5.85 (s, 4H, broad NH 2 ), 5.82 (s, 2H, aromatic), 3.80 (s, 3H, NMe), 3.36 (s, 3H, OMe). Anal. Calcd for C 8 H 12 F 3 N 3 O 4 S: C, 31.68; H, 3.99; N, %. Found: C, 32.00; H, 4.04; N, %. Preparation of 8-Methoxy-4-methyl-4H-bis[1,2,3]dithiazolo[4,5-b:5',4'-e]pyridin-2-ium Triflate [4a][OTf] A solution of S 2 Cl 2 (18.0 g, mol) in 20 ml DCE was added dropwise to a slurry of N-methyl-4-methoxy-2,6-diaminopyridinium triflate 7 (8.00 g, 26.4 mmol) in a mixture of 40 ml MeCN and 20 ml DCE, and the mixture set to reflux under N 2 for 4 h. The mixture was cooled to RT for 1 h, then at!20 EC for 3 h. The sparkling red microcrystalline solid was filtered off, washed with 2 50 ml DCE, 50 ml CS 2, 50 ml DCE, and pumped dry. Yield 8.3 g. This solid was boiled into 200 ml MeCN, and the solution filtered and the filtrate boiled down to 75 ml. Red crystals of [4a][OTf] appeared immediately on cooling to RT. The flask was cooled to!20 EC overnight, and the product collected by filtration and washed with DCE. Yield 5.23 g (12.3 mmol, 47 %), dec > 225 EC. 1 H NMR (δ, CD 3 CN): 4.01 (s, 3H, OMe), 3.61 (s, 3H, NMe). IR: 1523 (m), 1428 (m), 1402 (w), 1361 (m), 1271 (s), 1246 (s), 1224 (s), 1158 (m), 1055 (w), 1028 (s), 856 (m), 797 (s), 682 (s), 668 (w), 638 (s), 517 (w), 481 (m) cm -1. Anal. Calcd for C 8 H 6 F 3 N 3 O 4 S 5 : C, 22.58; H, 1.42; N, 9.88 %. Found: C, 22.60; H, 1.55; N, %. Addition of [BzEt 3 N][Cl] to a solution of [4a][OTf] in MeCN produced a blue-black precipitate of the corresponding chloride salt Page S3
4 [4a][Cl]. Treatment of the latter with a stoichiometric quantity of AgSbF 6 in MeCN afforded a deep red solution of the hexafluoroantimonate salt [4a][SbF 6 ], which was recrystallized from DCE for analytical and crystallographic purposes. IR: 1524 (m), 1407 (m), 1358 (m), 1219 (w), 1203 (w), 1138 (w), 1057 (w), 927 (w), 858 (w), 794 (s), 681 (s), 659 (vs), 476 (m) cm -1. Preparation of 8-methoxy-4-methyl-4H-bis[1,2,3]dithiazolo[4,5-b:5',4'-e]pyridin-3-yl 4a TDAE (300 µl, 260 mg, 1.3 mmol) was injected by syringe into a slurry of [MeOBPMe][OTf] (851 mg, 2.00 mmol) in 25 ml of bubble degassed MeCN held in EtOH at!20 EC. The TDAE dissolved over a period of minutes, to produce a dark grey solid in a red solution. After 30 min, the solid material, crude 8-methoxy-4-methyl-4H-bis[1,2,3]dithiazolo[4,5-b:5',4'-e]pyridin-3-yl 4a, was filtered off, washed with 3 15 ml MeCN, and dried in vacuo. Yield g, 1.70 mmol, 85%. IR: 1499 (w), 1241 (s), 1208 (m), 1115 (m), 1053 (m), 971 (w), 914 (w), 817 (w), 772 (m), 656 (m), 609 (w) cm -1. Thermal Conversion of 4a to 9 and 5a A slurry of 4a (0.470 g, 1.70 mmol) in 10 ml of degassed (4 freeze-pump-thaw cycles) DCE was warmed to 50 EC. The solid dissolved to afford a dark green solution that darkened and turned red within a few minutes. A heavy dark brown precipitate was also formed. After 20 min the mixture was allowed to cool to room temperature. After 36 hr the brown solid, the intermediate radical 9, was filtered off, washed with 20 ml DCE and 2 20 ml MeCN, and dried in vacuo. Yield, 330 mg (0.61mol, 72% for 9 from 4a). IR: 1604 (m), 1522 (s), 1353 (s), 1269 (s), 1212 (m), 1196 (w), 1129 (w), 1058 (s), 1039 (s), 863 (m), 796 (m), 719 (w), 682 (m), 624 (w), 572 (w) cm -1. Crude 9 (330 mg, 0.61 mol) was heated overnight at 130 EC/10-3 Torr. The resulting black solid, crude bis-1,2,3-dithiazolo-n-methyl-pyridone 5a (300 mg, 1.1 mmol, 67 % from 4a) was purified by sublimation in a tube furnace along a temperature gradient of 200!140 EC /10-3 Torr to afford purple blocks, mp > 250 EC. IR: 1509 (s), 1462 (s), 1392 (s), 1383 (s), 1366 (s), 1212 (m), 1054 (w), 862 (m), 853 (m), 791 (s), 724 (s), 676 (s), 635 (w), 857 (m), 486 (m), (w), 445 (m) cm -1. Anal. Calcd for C 6 H 3 N 3 OS: C, 27.57; H, 1.16; N, %. Found: C, 27.60; H, 1.31; N, %. Page S4
5 Cyclic Voltammetry Cyclic voltammetry was performed using a PINE Bipotentiostat, Model AFCClBP1, with scan rates of mv s -1 on solutions of [4a][OTf] in CH 3 CN (dried by distillation from P 2 O 5 and CaH 2 ) containing 0.1 M tetra-n-butyl-ammonium hexafluorophosphate. Potentials were scanned with respect to the quasi-reference electrode in a single compartment cell fitted with Pt electrodes and referenced to the Fc/Fc + couple of ferrocene at 0.38 V vs SCE. 1 The E pa - E pc separation of the reversible couples were within 10 % of that of the Fc/Fc + couple. EPR Spectra X-Band EPR spectra were recorded at ambient temperature using a Bruker EMX-200 spectrometer; samples of the radicals were dissolved in degassed CH 2 Cl 2. Hyperfine coupling constants were obtained by spectral simulation using Simfonia 2 and WinSim. X-ray Measurements Needles of [4a][SbF 6 ] and 5a were glued to glass fibers with epoxy. X-ray data were collected using omega scans with a Bruker APEX I CCD detector on a D8 3-circle goniometer and Mo K α (λ = D) radiation. The data were scanned using Bruker s SMART program and integrated using Bruker s SAINT software. 3 The structures were solved by direct methods using SHELXS-90 4 and refined by least-squares methods on F 2 using SHELXL-97 5 incorporated in the SHELXTL 6 suite of programs. 1 R. T. Boeré, K. H. Moock and M. Parvez, Z. Anorg. Allg. Chem., 1994, 620, WinEPR Simfonia, version 1.25; Bruker Instruments, Inc., Billerica, MA, SAINT, version 6.22 Bruker Advanced X-ray Solutions, Inc., Madison, WI, Sheldrick, G. M. SHELXS-90. Acta Crystallogr. A 1990, 46, Sheldrick, G. M. SHELXL-97. Program for the Refinement of Crystal Structures, University of Gottingen, Gottingen, Germany, SHELXTL, VERSION 6.12 Program Library for Structure Solution and Molecular Graphics, Bruker Advanced X-ray Solutions, Inc., Madison, WI, Page S5
6 Section S2 Gaussian 09 7 Archive Files. 1. Radical 4a, PCM based UB3LYP/6-311G(d,p) full optimization. 1 1 UNPC-RTO-OFFICE-2008 FOpt UB3LYP 6-311G(d,p) C7H6N3O1S4(2) USER 25 -Mar # ub3lyp/6-311g(d,p) opt scf=tight SCRF=(PCM, solvent=dic hloromethane) ub3lyp/6-311g(d,p) MeOBPMe - standard radical - full op timization with PCM 0,2 C, , , C, , , C, , , C, , , C, , , N, , , N, , , S, , , S, , , S, , , S, , , N, , , C, , , O, , , C, , , H, , , H, , , H, , , H, , , H, , , H, , , Version=IA32W-G09RevA.02 State=2-A HF= S2= S 2-1=0. S2A= RMSD=8.413e-009 RMSF=5.249e-005 Dipole= , , Quadrupole= , , , , , PG=C01 7 Gaussian 09, Revision A.02, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C. Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. W.; Morokuma, K.; Zakrzewski, V. G.; Voth, G., A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J., Gaussian, Inc., Wallingford CT, Page S6
7 2. Radical 9, PCM based UB3LYP/6-311G(d,p) full optimization. 1 1 UNPC-NEW-IR FOpt UB3LYP 6-311G(d,p) C7H6N3O1S4(2) OAKLAB 25-Mar # ub3lyp/6-311g(d,p) opt scf=tight SCRF=(PCM, solvent=dichlorome thane) UB3LYP/6-311G(d,p) PCM geometry optimization on Steve's mutant 0,2 C, , , C, , , C, , , C, , , C, , , N, , , S, , , S, , , N, , , N, , , S, , , S, , , C, , , C, , , O, , , H, , , H, , , H, , , H, , , H, , , H, , , Version=IA32W-G09RevA.02 State=2-A HF= S2= S2-1=0. S2A= RMSD=5.820e-009 RMSF=8.811e-006 Dipole= , , Quadrup ole= , , , , , PG= C01 Electronic Energies (in CH 2 Cl 2 ) of 4a and 9 Isomer E(tot) Hartrees kcal/mol ΔH (kcal/mol) 4a (O-Me) (N-Me) Page S7
8 3. Radical 4a, PCM UB3LYP/EPR-III/6-31G(d)//UB3LYP/6-311G(d,p) EPR properties. 1 1 UNPC-RTO2008 SP UB3LYP GenECP C7H6N3O1S4(2) USER 27-Mar # ub3lyp/genecp prop=epr scf=tight SCRF=(PCM, solvent=dichloromethane) UB3LYP/EPR-III/6-31G(d) Calculation of EPR properties - standard radic al - in DCM 0,2 C,0, , , C,0, , , C,0, , , C,0, , , C,0, , , N,0, , , N,0, , , S,0, , , S,0, , , S,0, , , S,0, , , N,0, , , C,0, , , O,0, , , C,0, , , H,0, , , H,0, , , H,0, , , H,0, , , H,0, , , H,0, , , Version=IA32W-G09RevA.02 St ate=2-a HF= S2= S2-1=0. S2A= RMSD=3.603e- 009 Dipole= , , Quadrupole= , , , , , PG=C01 5. Radical 9, PCM UB3LYP/EPR-III/6-31G(d)//UB3LYP/6-311G(d,p) EPR properties. 1 1 UNPC-NEW-IR SP UB3LYP GenECP C7H6N3O1S4(2) OAKLAB 26-Mar # ub3lyp/genecp prop=epr scf=tight SCRF=(PCM, solvent=dichloromethane) UB3LYP/EPR-III/6-31G(d) Calculation of EPR properties Steve's Mutant in DCM 0,2 C,0, , , C,0, , , C,0, , , C,0, , , C,0, , , N,0, , , S,0, , , S,0, , , N,0, , , N,0, , , S,0, , , S,0, , , C,0, , , C,0, , , O,0, , , H,0, , , H,0, , , H,0, , , H,0, , , H,0, , , H,0, , , Version=IA32W-G09RevA.02 State=2- A HF= S2= S2-1=0. S2A= RMSD=4.399e-009 Di pole= , , Quadrupole= , , , , , PG=C01 Page S8
9 6. Pyridone 5a, UB3LYP/6-311G(d,p) full optimization - Singlet State. 1 1 UNPC-RTO-OFFICE-2008 FOpt RB3LYP 6-311G(d,p) C6H3N3O1S4 USER 18-Ma r # b3lyp/6-311g(d,p) opt b3lyp/6-311g(d,p) closed shell sing let OBPMe - full optimization 0,1 C, , , C, , , C, , , C, , , C, , , N, , , N, , , S, , , S, , , S, , , S, , , N, , , C, , , O, , , H, , , H, , , H, , , Version= IA32W-G09RevA.02 State=1-A HF= RMSD=5.072e-009 RMSF=1.234 e-004 Dipole= , , Quadrupole= , , , , , PG=C01 7. Pyridone 5a, UB3LYP/6-311G(d,p) full optimization - Triplet State. 1 1 UNPC-RTO-OFFICE-2008 FOpt UB3LYP 6-311G(d,p) C6H3N3O1S4(3) USER 18 -Mar # ub3lyp/6-311g(d,p) opt scf=tight ub3lyp/6-311g(d,p) Tr iplet OBPMe - full optimization 0,3 C, , , C, , , C, , , C, , , C, , , N, , , N, , , S, , , S, , , S, , , S, , , N, , , C, , , O, , , H, , , H, , , H, , , Version= IA32W-G09RevA.02 State=3-A HF= S2= S2-1=0. S2A= RMSD=4.990e-009 RMSF=4.767e-005 Dipole= , , Quadrupole= , , , , , PG=C01 Page S9
10 Section S3 EPR spectra and hyperfine coupling constants. Radical 4a - Calculated Properties. Spin Densities from PCM UB3LYP/6311G(d,p) full optimization Coupling Constants from PCM UB3LYP/EPR-III/6-31G(d)//UB3LYP/6-311G(d,p) Number Atom Spin Density Coupling Constant (Gauss) 1 C(13) C(13) C(13) C(13) C(13) N(14) N(14) S(33) S(33) S(33) S(33) N(14) C(13) O(17) C(13) H(1) H(1) H(1) H(1) H(1) H(1) Experimental coupling constants (in Gauss) by spectral simulation: a N = (2N), (1N), a H =0.313 (3H) Linewidth = 0.259, g = Page S10
11 Radical 9 - Calculated Properties. Spin Densities from PCM UB3LYP/6311G(d,p) full optimization Coupling Constants from PCM UB3LYP/EPR-III/6-31G(d)//UB3LYP/6-311G(d,p) Number Atom Spin Density Coupling Constant (Gauss) 1 C(13) C(13) C(13) C(13) C(13) N(14) S(33) S(33) N(14) N(14) S(33) S(33) C(13) C(13) O(17) H(1) H(1) H(1) H(1) H(1) H(1) Experimental coupling constants (in Gauss) by spectral simulation: a N = (1N), (1N) Linewidth = 0.22, g = Page S11
12 Experimental (A), simulated (B) a,b and calculated (C) c EPR spectra of 9 (left) and 4a (right). A A B B C C Field (mt) Field (mt) a Simulated spectrum of 4a containg 5% of 9. b Linewidths for B and C were mt (9) and mt (4a). c Coupling constants from PCM UB3LYP/EPR-III/6-31G(d)//UB3LYP/6-311G(d,p) calculations. Page S12
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