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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supporting Information Abnormal N-Heterocyclic Carbene Based Nickel Complex for Catalytic Reduction of Nitroarenes GonelaVijaykumar, [a] and Swadhin K. Mandal* [a] [a] Department of Chemical Sciences, Indian Institute of Science Education and Research, Kolkata, Mohanpur , India. Fax: (+) , Contents 1 H NMR and 13 C NMR spectroscopy data of Hydrosilaylation Product... 1 H and 13 C NMR spectra images... X-ray crystallographic details... References... 1
2 1 H and 13 C NMR data Toluidine 1,2 1 H NMR (400 MHz, CDCl 3, 25 C):δ 6.99 (d, 2H, J= 7.6 Hz), 6.64 (d, 2H, J= 8.4 Hz), 3.54 (br s, 2H, - ), 2.27 (s, 3H) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ143.9, 129.8, 127.8, 115.3, 20.5 ppm. Aniline 1 1 H NMR: (400 MHz, CDCl 3, 25 C): δ 7.20 (t, 2H, J= 7.5 Hz), 6.81 (t, 1H, J= 7.5Hz), 6.71 (d, 2H, J = 7.5 Hz), 3.65 (br s, 2H, - ) ppm; 13 C NMR: (100 MHz, CDCl 3, 25 C): δ146.4, 129.3, 118.6, ppm. 4-Fluoroaniline 1 F 1 H NMR (400 MHz, CDCl 3, 25 C): δ 6.88 (m, 2H), 6.64 (m, 2H), 3.58 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ157.7, 155.3, 142.5, 116.2, 116.1, 115.9, ppm. 4-Chloroaniline 2 Cl 1 H NMR (400 MHz, CDCl 3, 25 C): δ 7.11 (d, 2H, J = 7.5 Hz), 6.61 (d, 2H, J = 7.5 Hz), 3.62 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ 145.0, 129.2, 123.2, ppm. 2
3 4-Bromoaniline 2 Br 1 H NMR (400 MHz, CDCl 3, 25 C): δ7.22 (d, 2H, J = 7.5 Hz), 6.55 (d, 2H, J = 7.5 Hz), 3.65 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C):δ145.6, 132.1, 116.8, ppm. 4-Iodoaniline 3 I 1 H NMR (400 MHz, CDCl 3, 25 C): δ7.42 (d, J= 7.5 Hz, 2H), 6.48 (d, J= 7.5 Hz, 2H), 3.67(br s, 2H, - NH2) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ 146.1, 137.9, 117.3, 79.4 ppm. 4-Methoxyaniline 1 OMe 1 H NMR (400 MHz, CDCl 3, 25 C): δ6.76 (d, 2H, J = 8 Hz), 6.60 (d, 2H, J= 8 Hz), 3.75 (s, 3H), 3.42(br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ152.9, 140.0, 116.5, 114.9, 55.8 ppm. 4-Aminoaniline 1 1 H NMR (100 MHz, CDCl 3, 25 C): δ6.57 (s, 4H), 3.33 (br s, 4H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ138.7, ppm. 3
4 3-Bromoaniline 2 Br 1 H NMR (400 MHz, CDCl 3, 25 C): δ7.02 (t, 1H, J = 8 Hz), 6.88 (d, 1H, J= 8 Hz), 6.83 (s, 1H),6.59 (d, 1H, J= 8 Hz),3.71(br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ147.8, 130.7, 123.1, 121.4, 117.8, ppm. 3-Chloroaniline 4 1 H NMR (400 MHz, CDCl 3, 25 C): δ7.07 (t, 1H, J = 8 Hz), 6.73 (dd, 1H, J= 8 Hz,), 6.67(t, 1H, J = 1.6 Hz), 6.53 (dd, 1H, J= 8 Hz), 3.71(br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ147.5, 134.8, 130.2, 118.4, 114.8, ppm. 3-Iodoaniline 5 Cl I 1 H NMR (400 MHz, CDCl 3, 25 C): δ (m, 2H), 6.88 (t, 1H, J= 8 Hz), 6.63 (d, 1H, J = 1.6 Hz), 3.53(br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ147.8, 130.8, 127.5, 123.8, 114.3, 95.0 ppm. m-phenylenediamine 6 1 H NMR (400 MHz, CDCl 3, 25 C): δ7.58 (d, 1H, J= 8 Hz), 7.48 (s, 1H), 7.28 (t, 1H, J = 7.6 Hz), 3.99 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C):δ147.6, 130.2, , ppm. 4
5 2-Fluoroaniline 6 F 1 H NMR (400 MHz, CDCl 3, 25 C): δ (m, 2H), (m, 2H), 3.67 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ152.9, 150.6, 134.6, 124.5, 124.3, 118.7, 118.6, 117.0, ppm. 2-Bromoaniline 7 Br 1 H NMR (400 MHz, CDCl 3, 25 C):δ7.42 (d, 1H, J= 8 Hz), 7.12 (t, 1H, J= 8 Hz), 6.77 (d, 1H, J = 8 Hz), 7.64 (t, 1H, J= 8 Hz), 4.07 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ144.1, 132.7, 128.4, 119.5, 115.8, ppm. 1-Aminonaphthalene 2 1 H NMR (400 MHz, CDCl 3, 25 C): δ (m, 2H), (m, 2H), (m, 2H), 6.81 (d, 1H, J= 8 Hz), δ 4.15 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ 142.0, 134.3, 128.4, 126.2, 125.7, 124.7, 123.5, 120.7, 118.8, ppm. 3-Aminobenzylalcohol 8 OH 1 H NMR (400 MHz, CDCl 3 J= 8 Hz, 25 C): δ7.16 (t, 1H, J = 8 Hz), 6.75 (d, 1H, J= 7.5 Hz), 6.69 (s, 1H), 6.62 (d, 1H, J= 7.5 Hz), 4.59 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3 J= 8 Hz, 25 C): δ146.5, 142.1, 129.4, 117.0, 114.3, 113.5, ppm. 5
6 3-Aminobenzonitrile 9 CN 1 H NMR (400 MHz, CDCl 3, 25 C): δ7.23 (t, 1H, J = 7.5 Hz), 7.01 (d, 1H, J = 7.5 Hz), 6.89 (s, 1H), 6.87 (d, 1H, J = 7.5Hz), 3.91 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ 147.1, 130.1, 121.8, 119.3, 117.5, ppm. 12) 3-Aminostyrene 10 1 H NMR (400 MHz, CDCl 3, 25 C): δ7.14 (t, 1H, J = 7.5 Hz), 6.83 (d, 1H, J= 7.5 Hz), 6.74 (br s, 1H), 6.67 (dd, 1H, J1= 18 Hz, J2= 12 Hz), 6.63 (d, 1H, J = 7.5 Hz), 5.72 (d, 1H, J= 18 Hz), 5.23 (d, 1H, J= 12 Hz), 3.61 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ146.4, 138.6, 136.9, 129.3, 116.9, 114.7, 113.5, ppm. 8-Aminoquinoline 4 N 1 H NMR (400 MHz, CDCl 3, 25 C): δ 8.77 (d, 1H, J = 4 Hz), 8.08 (d, 1H, J = 7.5 Hz), (m, 2H), 7.17 (d, J = 7.5 Hz, 1H), 6.95 (d, J = 8 Hz, 1H), 4.99 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ 147.5, 144.0, 138.5, 136.1, 128.9, 127.5, 121.4, 116.1, ppm. 6-Aminoquinoline 3 H 2 N N 1 H NMR (400 MHz, CDCl 3, 25 C): δ 8.66 (d, 1H, J = 7.5 Hz), 7.92 (dd, 1H, J= 8.4, 4.2 Hz), 7.29 (dd, 1H, J = 7.7, 3.5 Hz), 7.17 (dd, 1H, J = 8.9, 2.6 Hz), 6.91 (d, 1H, J = 2.4 Hz), 3.95 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ 146.9, 144.7, 143.4, 134.0, 130.6, 129.9, 121.7, 121.5, ppm. 6
7 6-Amino-1,4-benzodioxane 3 H 2 N O O 1 H NMR (400 MHz, CDCl 3, 25 C): δ6.67 (d, 1H, J = 6.8 Hz), 6.24 (d, 1H, J = 2 Hz), 6.20 (dd, 1H, J=2 Hz, J = 2 Hz), (m, 2H), (m, 2H), 3.39 (br s, 2H, - ) ppm; 13 C NMR (100 MHz, CDCl 3, 25 C): δ 143.8, 140.7, 136.4, 117.5, 108.6, 104.1, 64.6, 64.1 ppm. Fig. S1: The 1 H NMR spectrum (CDCl 3 ) of complex 1. Ph N Ph Ph Cl Ni N Cl N N Ph 7
8 Fig. S2: The 13 C NMR spectrum (CDCl 3 ) of complex 1. Ph N Ph Ph Cl Ni N Cl N N Ph Fig. S3: The 1 H NMR spectrum (CDCl 3 ) of toluidine. 8
9 Fig. S4: The 13 C NMR spectrum (CDCl 3 ) of toluidine. Fig. S5: The 1 H NMR spectrum (CDCl 3 ) of aniline. 9
10 Fig. S6: The 13 C NMR spectrum (CDCl 3 ) of aniline. Fig. S7: 1 H NMR spectrum (CDCl 3 ) of 4-Fluoroaniline. F 10
11 Fig. S8: The 13 C NMR spectrum (CDCl 3 ) of 4-Fluoroaniline. F Fig. S9: 1 H NMR spectrum (CDCl 3 ) of p-anisidine. OMe 11
12 Fig. S10: 13 C NMR spectrum (CDCl 3 ) of p-anisidine. OMe Fig. S11: 1 H NMR spectrum (CDCl 3 ) of 4-Chloroaniline. Cl 12
13 Fig. S12: The 13 C NMR spectrum (CDCl 3 ) of 4-Chloroaniline. Cl Fig. S13: The 1 H NMR spectrum (CDCl 3 ) of 4-Bromoaniline. Br 13
14 Fig. S14: The 13 C NMR spectrum (CDCl 3 ) of 4-Bromoaniline. Br Fig. S15: The 1 H NMR spectrum (CDCl 3 ) of 4-Iodoaniline. I 14
15 Fig. S16: The 13 C NMR spectrum (CDCl 3 ) of 4-Iodoaniline. I Fig. S17: The 1 H NMR spectrum (CDCl 3 ) of 4-Aminoaniline. 15
16 Fig. S18: The 13 C NMR spectrum (CDCl 3 ) of 4-Aminoaniline. Fig. S19: The 1 H NMR spectrum (CDCl 3 ) of 3-Chloroaniline. Cl 16
17 Fig. S20: The 13 C NMR spectrum (CDCl 3 ) of 3-Chloroaniline. Cl Fig. S21: The 1 H NMR spectrum (CDCl 3 ) of 3-Bromoaniline. Br 17
18 Fig. S22: The 13 C NMR spectrum (CDCl 3 ) of 3-Bromoaniline. Br Fig. S23: The 1 H NMR spectrum (CDCl 3 ) of 3-Iodoaniline. I 18
19 Fig. S24: The 13 C NMR spectrum (CDCl 3 ) of 3-Iodoaniline. I Fig. S25: The 1 H NMR spectrum (CDCl 3 ) of m-phenylenediamine. 19
20 Fig. S26: The 13 C NMR spectrum (CDCl 3 ) of m-phenylenediamine. Fig. S27: The 1 H NMR spectrum (CDCl 3 ) of 3-Aminobenzonitrile. CN 20
21 Fig. S28: The 13 C NMR spectrum (CDCl 3 ) of 3-Aminobenzonitrile. CN Fig. S29: The 1 H NMR spectrum (CDCl 3 ) of 2-Fluoroaniline. F 21
22 Fig. S30: The 13 C NMR spectrum (CDCl 3 ) of 2-Fluoroaniline. F Fig. S31: The 1 H NMR spectrum (CDCl 3 ) of 2-Bromoaniline. Br 22
23 Fig. S32: The 13 C NMR spectrum (CDCl 3 ) of 2-Bromoaniline. Br Fig. S33: The 1 H NMR spectrum (CDCl 3 ) of 3-Amino benzylalcohol. OH 23
24 Fig. S34: The 13 C NMR spectrum (CDCl 3 ) of 3-Amino benzylalcohol. OH Fig. S35: The 1 H NMR spectrum (CDCl 3 ) of 1-Aminonaphthalene. 24
25 Fig. S36: The 13 C NMR spectrum (CDCl 3 ) of 1-Aminonaphthalene. Fig. S37: The 1 H NMR spectrum (CDCl 3 ) of 8-Aminoquinoline. N 25
26 Fig. S38: The 13 C NMR spectrum (CDCl 3 ) of 8-Aminoquinoline. N Fig. S39: The 1 H NMR spectrum (CDCl 3 ) of 6-Aminoquinoline. H 2 N N 26
27 Fig. S40: The 13 C NMR spectrum (CDCl 3 ) of 6-Aminoquinoline. H 2 N N Fig. S41: The 1 H NMR spectrum (CDCl 3 ) of 3-Aminostyrene. 27
28 Fig. S42: The 13 C NMR spectrum (CDCl 3 ) of 3-Aminostyrene. Fig. S43: The 1 H NMR spectrum (CDCl 3 ) of 6-Amino-1,4-benzodioxane. H 2 N O O 28
29 Fig. S44: The 13 C NMR spectrum (CDCl 3 ) of 6-Amino-1,4-benzodioxane. H 2 N O O 29
30 Fig. S45: The stacked 1 H NMR spectra (CDCl 3 ) recorded from the reaction mixture of stoichiometric reactions between complex 1 and nitrobenzene as well as PhSiH 3 and compared with 1 H NMR spectra of all starting reactants. 30
31 Fig. S46: The 13 C NMR spectrum (CDCl 3 ) recorded from the reaction mixture of the stoichiometric reaction between complex 1 and with PhSiH 3 (top) in comparison with that recorded for catalyst 1 (bottom). Fig. S47: The 29 Si NMR spectrum (CDCl 3 ) obtained from the reaction mixture of stoichiometric reaction of complex 1 with PhSiH 3. 31
32 Table S1. Crystal Data and Details of the Structure Determination for 1. CCDC Empirical formula C 39 H 44 ClN 2 Ni 0.5 Formula weight Temperature (K) 100 Wavelength (A ) Crystal system triclinic Space group P-1 Unit cell dimensions a ( Å) (6) b (Å ) (5) c (Å ) (8) α ( ) (4) β ( ) (4) γ( ) (4) Volume (Å 3 ) (18) Z 2 Calculated density (Mg/m3) Absorption coefficient (mm-1) F(000) 646 Crystal size (mm) 0.31 x 0.42 x 0.56 Theta range for data collection( ) 1.9, 28.3 Dataset -15: 13 ; -16: 16 ; -19: 17 Tot.,Uniq. Data, R(int) 13758, 8387, Observed Data [I > 0.0 sigma(i)] 7097 Nref, Npar 8387, 393 R, wr2, S , , 1.05 Min. and Max. Resd. Dens. [e/ang^3] -0.45,
33 Table S2. Selected bond distances (Å) and angles ( ) for 1. Complex 1 Bond distances (Å) Bond angles ( ) Ni1 -Cl (5) Cl1 -Ni1 -C (5) Ni1 -C (17) C1 -Ni1 -C1_a N1 -C (2) Cl1 -Ni1 -Cl1_a N1 -C (2) Cl1 -Ni1 -C1_a 88.08(5) N1 -C (2) Cl1_a -Ni1 -C (5) N2 -C (2) C1 -N1 -C (15) N2 -C (2) C1 -N1 -C (14) C3 -N1 -C (15) Table S3. Final Coordinates and Equivalent Isotropic Displacement Parameters of the non-hydrogen atoms for 1 Atom x y z U(eq) [Ang^2] Ni1 1/2 1/2 1/ (1) Cl (4) (4) (3) (1) N (12) (12) (9) (4) N (13) (12) (9) (4) C (15) (15) (11) (5) C (15) (15) (12) (5) C (15) (15) (11) (5) C (15) (14) (12) (4) C (16) (15) (12) (5) C (17) (16) (14) (5) C (18) (16) (14) (6) C (17) (16) (13) (5) C (16) (15) (12) (5) C (17) (16) (13) (5) 33
34 C (17) (18) (14) (6) C (19) (17) (13) (6) C (17) (16) (13) (5) C (2) (18) (14) (6) C (18) (19) (16) (6) C (16) (15) (11) (5) C (17) (16) (12) (5) C (17) (17) (13) (5) C (18) (17) (13) (5) C (18) (16) (13) (5) C (17) (15) (12) (5) C (16) (16) (13) (5) C (2) (18) (14) (6) C (2) (2) (17) (8) C (2) (19) (17) (7) C (2) (17) (16) (6) C (18) (16) (14) (5) C (15) (15) (12) (5) C (16) (17) (12) (5) C (19) (2) (14) (6) C (2) (2) (16) (8) C (19) (2) (16) (7) C (16) (17) (13) (5) C (19) (18) (14) (6) C (2) (2) (2) (8) C (2) (2) (17) (8) 34
35 C (19) (18) (13) (6) C (2) (2) (15) (7) C (2) (2) (15) (7) Table S4. (An)isotropic Displacement Parameter for 1 Atom U(1,1) or U U(2,2) U(3,3) U(2,3) U(1,3) U(1,2) Ni (2) (2) (2) (1) (1) (1) Cl (2) (2) (2) (2) (2) (2) N (7) (6) (7) (5) (5) (5) N (7) (7) (6) (5) (5) (5) C (8) (8) (8) (6) (6) (6) C (8) (8) (8) (6) (6) (6) C (8) (8) (8) (6) (6) (6) C (8) (7) (8) (6) (6) (6) C (8) (8) (8) (7) (7) (7) C (9) (8) (10) (8) (8) (7) C (10) (9) (10) (8) (8) (7) C (9) (9) (9) (7) (7) (7) C (8) (8) (8) (7) (7) (7) C (9) (9) (9) (7) (7) (7) C (9) (10) (10) (8) (8) (8) C (10) (10) (9) (8) (8) (8) C (9) (9) (9) (7) (7) (7) C (11) (10) (10) (9) (8) (9) C (9) (10) (13) (10) (9) (8) 35
36 C (8) (8) (8) (6) (6) (7) C (9) (9) (9) (7) (7) (7) C (8) (10) (9) (8) (7) (7) C (9) (9) (9) (8) (7) (8) C (10) (9) (9) (7) (8) (8) C (9) (9) (8) (7) (7) (7) C (8) (8) (9) (7) (7) (7) C (12) (10) (10) (8) (9) (9) C (15) (13) (12) (11) (11) (11) C (13) (11) (14) (11) (11) (10) C (11) (9) (12) (9) (10) (8) C (9) (9) (10) (8) (8) (7) C (8) (8) (8) (7) (7) (7) C (8) (9) (8) (7) (7) (7) C (11) (13) (9) (9) (8) (10) C (11) (16) (12) (12) (9) (11) C (10) (13) (12) (10) (9) (9) C (8) (9) (9) (8) (7) (7) C (10) (11) (10) (9) (8) (9) C (12) (12) (17) (12) (12) (10) C (12) (14) (13) (11) (10) (11) C (10) (11) (9) (8) (8) (9) C (11) (13) (10) (10) (9) (10) C (15) (12) (10) (9) (10) (11) 36
37 References: 1. U. Sharma, P. K. Verma, N. Kumar, V. Kumar, M. Bala and B. Singh, Chem. Eur. J., 2011, 17, U. Sharma, N. Kumar, P. K. Verma, V. Kumar and B. Singh, Green Chem., 2012, 14, R. Dey, N. Mukherjee, S. Ahammed and B. C. Ranu, Chem. Commun., 2012, 48, K. Junge, B. Wendt, N.Shaikh and M. Beller, Chem. Commun., 2010, 46, R. V. Jagadeesh, D. Banerjee, P. B. Arockiam, H. Junge, K. Junge, M.-M. Pohl, J.Radnik, A. Brückner and M. Beller Green Chem., 2015, 17, R. J. Rahaim and R. E. Maleczka, Jr.,Org. Lett,.2005, 7, E.Kumaran, V. S.Sridevi and W. K. Leong, Organometallics, 2010, 29, H. Yang,Y. Li, M. Jiang, J. Wang and H. Fu, Chem. Eur. J., 2011, 17, R. J. Rahaim and R. E. Maleczka, Org. Lett., 2005,7, E. Vasilikogiannaki, C. Gryparis, V. Kotzabasaki, I. N. Lykakis and M. Stratakis, Adv. Synth. Catal., 2013, 355,
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College of Life Science, Dalian Nationalities University, Dalian , PR China.
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Supporting Information Multifunctinality and Crystal Dynamics of Highly Stable Porous Metal-Organic Framework [Zn 4 O(NTB) 2 ] Eun Young Lee, Seung Yeon Jang, and Myunghyun Paik Suh* School of Chemistry,
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Synthesis, Characterization, and Computational Study of Three-Coordinate SNS-Copper(I) Complexes Based on Bis-Thione Precursors
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Electronic, Crystal Chemistry, and Nonlinear Optical Property Relationships. or W, and D = P or V)
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Supporting Information Gold-catalyzed Cycloisomerization of 1,6-Diyne-4-en-3-ols to form Naphthyl Ketone Derivatives. Jian-Jou Lian and Rai-Shung Liu* Department of Chemistry, National Tsing-Hua University,
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Supporting Information Pb 3 B 6 O 11 F 2 : A First Noncentrocentric Lead Fluoroborate with Large Second Harmonic Generation Response Hongyi Li, a Hongping Wu, a * Xin Su, a Hongwei Yu, a,b Shilie Pan,
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