Mild Aliphatic and Benzylic hydrocarbon C H Bond Chlorination Using Trichloroisocyanuric Acid (TCCA)
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1 Mild Aliphatic and Benzylic hydrocarbon C H Bond Chlorination Using Trichloroisocyanuric Acid (TCCA) Sascha H. Combe, Abolfazl Hosseini, Alejandro Parra, # and Peter R. Schreiner*, Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17, Giessen, Germany; prs@org.chemie.uni-giessen.de # Departamento de Química Orgánica, Universidad Autónoma de Madrid Cantoblanco, Madrid, Spain Contents Spectral data... S2 Mechanistic studies - chain length... S18 Computations... S19 Computations at the B3LYP-D3/6-31G(d,p)/CPCM (solvent: CH2Cl2) level of theory... S19 Computations at the M06-2X/cc-pVTZ/CPCM (solvent: CH2Cl2) level of theory. S19 Literature... S32 S1
2 Spectral data S2
3 S3
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18 Mechanistic studies - chain length Chain length = yield 13 / NHPI in mol% Average chain length = sum of chain length / sum of experiments Table S1. Radical chain length initiated by NHPI 1 h NHPI [equiv.] 13 [%] a Chain length Average chain length (1.8) h (2.2) Table S2. Radical chain length initiated by NHPI and CBr4 1 h NHPI [equiv.] CBr4 [equiv.] 13 [%] a Chain length Average chain length (1.9) h (2.6) a Yield determined by 1 H-NMR with dimethylterephthalate as internal standard. S18
19 Computations Computations at the B3LYP-D3/6-31G(d,p)/CPCM (solvent: CH2Cl2) level of theory All computations based on Kohn-Sham density functional theory (DFT) 1 were performed with the program package Gaussian09. 2 Geometry optimizations were performed with the B3LYP functional combination. 3 Empirical dispersion corrections by Grimme (D3-BJ) 4 were used to treat non-covalent interactions. Frequency analyses were performed to confirm that the optimized structures are local minima or transition states, and also to obtain the thermodynamic corrections to Gibbs free energies. For copper we utilized a cc-pvdz-dk all-electron basis set, 5 while for all other atoms a 6-31G(d,p) basis set was employed. Intrinsic reaction coordinate (IRC) calculations were performed to ensure that the obtained transition states do connect the reactants and products. Solution-phase (CPCM) single-point energy calculations were conducted on the basis of the gas phase optimized structures using dichloromethane as solvent at 298 K and 1 atm. Computations at the M06-2X/cc-pVTZ/CPCM (solvent: CH2Cl2) level of theory All structures were optimized at the M06-2X/cc-pVTZ/CPCM (solvent: CH2Cl2) level of theory 6 utilizing the Gaussian09 2 program package. The computed structures were characterized as minima on the potential energy hypersurface by vibrational frequency computations (with minima having only real frequencies) that also provided thermal corrections and zero-point vibrational energies (ZPVEs). Table S3. Absolute energies in au at the B3LYP-D3/6-31G(d,p)/CPCM (solvent: CH2Cl2) level of theory Structure HF ZPVE H298 G298 1 (NHPI) (PINO) (PhMe) (Bn ) (CA) cyanuric acid monochloroisocyanuric acid monochloroisocyanuric acid S19
20 Structure HF ZPVE H298 G298 Cu(OAc) CuOAc AcOH H A TS B TS a C TS TS CBr TS Br3C Br3C TS CHBr S20
21 Table S4. Energies of the reactions in kcal mol 1 at the B3LYP-D3/6-31G(d,p)/CPCM (solvent: CH2Cl2) level of theory Reaction ΔH298 ΔG H Cu(OAc)2 + H CuOAc + AcOH Cu(OAc)2 2 + CuOAc + AcOH monochloroisocyanuric acid monochloroisocyanuric acid cyanuric acid Scheme S1. Generation of benzyl radical 3 (energies in kcal mol 1 ) S21
22 Scheme S2. Generation of benzyl chloride 4a (energies in kcal mol 1 ) Scheme S3. Regeneration of benzyl radical 24 (energies in kcal mol -1 ) S22
23 Scheme S4. Reaction of benzyl radical with CBr4 (energies in kcal mol 1 ) Scheme S5. Regeneration of benzyl radical 24 (energies in kcal mol 1 ) S23
24 Cartesian coordinates of all computed structures at the the B3LYP-D3/6-31G(d,p)/CPCM (solvent: CH2Cl2) level of theory NHPI 1 (C2v) C C C C C C H H H H C O O N C O H PINO 2 (C2v) C C C C C C H H H H C O O N C O PhMe 3 (Cs) C C C C C C H H H H H C H H H BnCl 4a (Cs) C C C C C C H H H H H C H H Cl BnBr 5 (Cs) C C C C C C H H H H H C H H Br TCCA 23 (C3) S24
25 C O N N C C O O N Cl Cl Cl Bn 24 (C2v) C C C C C C H H H H H C H H dichloroisocyanuric acid 25(Cs) C O N N C C O O N Cl Cl dichloroisocyanuric acid 26 (C2v) C O N N C C O O N Cl Cl H Br3C (C3v) C Br Br Br CBr4 (D2d) C Br Br Br Br cyanuric acid 27 (Cs) C O N N C C O O N H H H cyanuric acid (C1) C O N N C C O O N H H S25
26 HCBr3 (Cs) C Br Br Br H monochloroisocyanuric acid (C2v) C O N N C C O O N H H Cl monochloroisocyanuric acid (C1) C O N N C C O O N H Cl Complex A C C C C C C H H H C C C C C C C C H H H H O O N O H H C H H H Complex B C C C C C C H H H H H C H H C O N N C C O O N Cl Cl Cl TS2 S26
27 C C C C C C H H H H H C H H Cl N N N Cl Cl C C C O O O Cl Complex C C O N N C C O O N Cl Cl C C C C C C H H H H H C H H H TS3 C C C C C C H H H H H C H H H C O N N C C O O N Cl Cl TS3 C C C C C C H H H H H C H S27
28 H H C O N N C C O O N Cl Cl DCCA enol 28 (Cs) C O N N C C O O N Cl Cl H S28
29 Table S5. Absolute energies in au at the M06-2X/cc-pVTZ/CPCM (CH2Cl2) level of theory Structure HF ZPVE H298 G298 3 (PhMe) a (BnCl) (BnBr) (TCCA) (Bn ) (DCCA ) (DCCA) , (CA) cyanuric acid monochloroisocyanuric acid monochloroisocyanuric acid CBr Br3C HCBr Table S6. Energies of the reactions in kcal mol 1 at the M06-2X/cc-pVTZ/CPCM (CH2Cl2) level of theory Reaction ΔH298 ΔG monochloroisocyanuric acid monochloroisocyanuric acid cyanuric acid CBr4 Br3C Br3C HCBr a S29
30 Cartesian coordinates of all computed structures at the M06-2X/cc-pVTZ/CPCM (CH2Cl2) level of theory PhMe 3 (Cs) BnCl 4a (Cs) BnBr 5 (Cs) TCCA 23 (C3) Bn 24 (C2v) dichloroisocyanuric acid 25(Cs) S30
31 dichloroisocyanuric acid 26 (C2v) Br3C (C3v) CBr4 (D2d) cyanuric acid 27 (Cs) HCBr3 (Cs) monochloroisocyanuric acid (C2v) monochloroisocyanuric acid (C1) cyanuric acid (C1) S31
32 Literature (1) Calais, J.-L. Int. J. Quantum Chem. 1993, 47, 101. (2) 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. J.; Heyd, J.; Brothers, E. N.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A. P.; 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. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J.; Gaussian, Inc.: Wallingford, CT, USA, (3) (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648; (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785. (4) (a) Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, ; (b) Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, (5) (a) Dunning Jr., T. H. J. Chem. Phys. 1989, 90, 1007; (b) Balabanov, N. B.; Peterson, K. A. J. Chem. Phys. 2005, 123, (6) (a) Zhao, Y.; Truhlar, D. G. Theor. Chem. Account 2007, 120, 215; (b) Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157. S32
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