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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Syntheses and structures of copper complexes of 3-(6-(1H-pyrazol-1-yl)pyridin-2-yl)pyrazol-1-ide and their excellent performance in the syntheses of nitriles and aldehydes Da-Wei Tan, a Jing-Bo Xie, a Qi Li, a Hong-Xi Li, a, * Jun-Chi Li, a Jian-Ping Lang a,b * a College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou , P. R. China b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai , P. R. China S1
2 Table of Contents Figure S1. One-dimensional chain (extended along the b axis) formed via H-bonding interactions in 4. S4 Figure S2. The calculated isotope pattern (top) and the observed patterns (below) of the [{(Cu(NO 3 ))(μ-pzpypz)} 2 + NO 3 + 2CH 3 CN] + cation in the positive-ion ESI mass spectrum of 1. S4 Figure S3. The calculated isotope pattern (top) and the observed patterns (below) of the [CuClO 4 (pzpypzh)cuoch 3 (pzpypz)] + cation in the positive-ion ESI mass spectrum of 2. S4 Figure S4. The calculated isotope pattern (top) and the observed patterns (below) of the [{Cu 2 (μ-so 4 )(μ-pzpypz) 2 } + HSO 4 + 2MeOH + 4H 2 O + CH 3 CN] + cation in the positive-ion ESI mass spectrum of 3. S5 Figure S5. The calculated isotope pattern (top) and the observed patterns (below) of the [{(CuI)(μ-pzpypz)} 2 + I + 3H 2 O + 4CH 3 CN] + cation in the positive-ion ESI mass spectrum of 5. S5 The 1 H and 13 C NMR data of benzonitrile, 2-methylbenzonitrile, 3-methylbenzonitrile, 4-methylbenzonitrile, 2-methoxybenzonitrile, 3-methoxybenzonitrile, 4-methoxybenzonitrile, 4-chlorobenzonitrile, 4-nitrobenzonitrile, 3,4-(methylenedioxy)benzonitrile, 1-naphthonitrile, 3-cyanopyridine, 2-thiophenecarbonitrile, benzaldehyde, 2-methylbenzaldehyde, 3-methylbenzaldehyde, 4-methylbenzaldehyde, 2-methoxybenzaldehyde, 3-methoxybenzaldehyde, 4-methoxybenzaldehyde, 4-chlorobenzoic aldehyde, 4-nitrobenzaldehyde, 3-pyridinecarboxaldehyde, 2-thenaldehyde S6 The 1 H and 13 C NMR spectra of 1-(6-(1H-pyrazol-1-yl)pyridin-2-yl)ethanone S8 The 1 H and 13 C NMR spectra of 1-(6-(1H-pyrazol-1-yl)pyridin-2-yl)-3-(dimethylamino)prop- 2-en-1-one S9 The 1 H and 13 C NMR spectra of 2-(1H-pyrazol-1-yl)-6-(1H-pyrazol-3-yl)pyridine S10 The 1 H and 13 C NMR spectra of the product benzonitrile S11 The 1 H and 13 C NMR spectra of the product 2-methylbenzonitrile S12 The 1 H and 13 C NMR spectra of the product 3-methylbenzonitrile S13 The 1 H and 13 C NMR spectra of the product 4-methylbenzonitrile S14 The 1 H and 13 C NMR spectra of the product 2-methoxybenzonitrile S15 The 1 H and 13 C NMR spectra of the product 3-methoxybenzonitrile S16 The 1 H and 13 C NMR spectra of the product 4-methoxybenzonitrile S17 S2
3 The 1 H and 13 C NMR spectra of the product 4-chlorobenzonitrile S18 The 1 H and 13 C NMR spectra of the product 4-nitrobenzonitrile S19 The 1 H and 13 C NMR spectra of the product 1-naphthonitrile S20 The 1 H and 13 C NMR spectra of the product 3,4-(methylenedioxy)benzonitrile S21 The 1 H and 13 C NMR spectra of the product 3-cyanopyridine S22 The 1 H and 13 C NMR spectra of the product 2-thiophenecarbonitrile S23 The 1 H and 13 C NMR spectra of the product benzaldehyde S24 The 1 H and 13 C NMR spectra of the product 2-methylbenzaldehyde S25 The 1 H and 13 C NMR spectra of the product 3-methylbenzaldehyde S26 The 1 H and 13 C NMR spectra of the product 4-methylbenzaldehyde S27 The 1 H and 13 C NMR spectra of the product 2-methoxybenzaldehyde S28 The 1 H and 13 C NMR spectra of the product 3-methoxybenzaldehyde S29 The 1 H and 13 C NMR spectra of the product 4-methoxybenzaldehyde S30 The 1 H and 13 C NMR spectra of the product 4-chlorobenzoic aldehyde S31 The 1 H and 13 C NMR spectra of the product 4-nitrobenzaldehyde S32 The 1 H and 13 C NMR spectra of the product 3-pyridinecarboxaldehyde S33 The 1 H and 13 C NMR spectra of the product 2-thenaldehyde S34 S3
4 Figure S1. One-dimensional chain (extended along the b axis) formed via H-bonding interactions in m/z Figure S2. The calculated isotope pattern (top) and the observed patterns (below) of the [{(Cu(NO 3 ))(μ-pzpypz)} 2 + NO 3 + 2CH 3 CN] + cation in the positive-ion ESI mass spectrum of m/z Figure S3. The calculated isotope pattern (top) and the observed patterns (below) of the [CuClO 4 (pzpypzh)cuoch 3 (pzpypz) + 3MeOH] + cation in the positive-ion ESI mass spectrum of 2. S4
5 m/z Figure S4. The calculated isotope pattern (top) and the observed patterns (below) of the [{Cu 2 (μ-so 4 )(μ-pzpypz) 2 } + HSO 4 + 2MeOH + 4H 2 O + CH 3 CN] + cation in the positive-ion ESI mass spectrum of m/z Figure S5. The calculated isotope pattern (top) and the observed patterns (below) of the [{(CuI)(μ-pzpypz)} 2 + I + 3H 2 O + 4CH 3 CN] + cation in the positive-ion ESI mass spectrum of 5. S5
6 benzonitrile: 1 H NMR (400 MHz, CDCl 3, ppm): δ 7.47 (t, J = 8.0Hz, 1H), 7.60 (d, J = 8.0Hz, 1H), 7.64 (d, J = 8.0Hz, 2H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 112.2, 118.6, 128.9, 132.0, methylbenzonitrile: 1 H NMR (400 MHz, CDCl 3, ppm): δ 2.53 (s, 3H), 7.26 (d, J = 8.0Hz, 1H), 7.31 (t, J = 8.0Hz, 1H), 7.47 (t, J = 8.0Hz, 1H), 7.56 (d, J = 8.0Hz, 1H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 20.2, 112.4, 117.9, 126.0, 130.0, 132.2, 132.4, methylbenzonitrile: 1 H NMR (400 MHz, CDCl 3, ppm): δ 2.37 (s, 3H), 7.34 (t, J = 8.0Hz, 1H), 7.41 (t, J = 8.0Hz, 3H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 20.8, 111.8, 118.7, 128.7, 132.1, 133.4, methylbenzonitrile: 1 H NMR (400 MHz, CDCl 3, ppm): δ 2.42 (s, 3H), 7.27 (d, J = 8.0Hz, 2H), 7.52 (d, J = 8.0Hz, 2H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 21.7, 109.1, 119.0, 129.7, 131.9, methoxybenzonitrile: 1 H NMR (400 MHz, CDCl 3, ppm): δ 2.53 (s, 3H), 7.27 (t, J = 8.0Hz, 1H), 7.31 (t, J = 8.0Hz, 1H), 7.48 (t, J = 8.0Hz, 1H), 7.57 (t, J = 8.0Hz, 1H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 20.2, 112.4, 117.9, 126.0, 130.0, 132.2, 132.4, methoxybenzonitrile: 1 H NMR (400 MHz, CDCl 3, ppm): δ 3.83 (s, 3H), 7.13 (d, J = 8.0Hz, 2H), 7.23 (d, J = 8.0Hz, 1H), 7.37 (t, J = 8.0Hz, 1H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 55.3, 112.9, 116.6, 118.6, 119.1, 124.2, 130.1, methoxybenzonitrile: 1 H NMR (400 MHz, CDCl 3, ppm): δ 3.86 (s, 3H), 6.95 (d, J = 8.0Hz, 2H), 7.58 (d, J = 8.0Hz, 2H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 55.5, 103.9, 114.7, 119.2, 133.9, chlorobenzonitrile: 1 H NMR (400 MHz, CDCl 3, ppm): δ 7.47 (d, J = 8.0Hz, 2H), 7.61 (d, J = 8.0Hz, 2H). 13 C NMR (125 MHz, CDCl 3, ppm): δ 110.7, 117.9, 129.6, 133.3, nitrobenzonitrile: 1 H NMR (400 MHz, CDCl 3, ppm): δ 7.89 (d, J = 8.0Hz, 2H), 8.35 (d, J = 8.0Hz, 2H). 13 C NMR (125 MHz, CDCl 3, ppm): δ 116.7, 118.2, 124.2, 133.4, ,4-(Methylenedioxy)benzonitrile: 1 H NMR (400 MHz, CDCl 3, ppm): δ 6.08 (s, 2H), 6.87 (d, J = 8.0Hz, 1H), 7.02 (s, 1H), 7.21 (d, J = 8.0Hz, 1H). 13 C NMR (125 MHz, CDCl 3, ppm): δ 102.1, 104.8, 109.0, 111.2, 118.8, 128.0, 147.9, naphthonitrile: 1 H NMR (400 MHz, CDCl 3, ppm): δ 7.47 (t, J = 8.0Hz, 1H), 7.58 (t, J = 8.0Hz, 1H), 7.64 (t, J = 8.0Hz, 1H), 7.86 (t, J = 8.0Hz, 2H), 8.02 (d, J = 8.0Hz, 1H), 8.19 (d, J = 8.0Hz, 1H). 13 C NMR (125 MHz, CDCl 3, ppm): δ 110.0, 117.8, 124.8, 127.3, 128.4, 128.5, 132.1, 132.4, 132.7, cyanopyridine: 1 H NMR (400 MHz, CDCl 3, ppm): δ 7.49 (t, J = 8.0Hz, 1H), 8.02 (d, J = 8.0Hz, 1H), 8.86 (s, 1H), 8.92 (s, 1H). 13 C NMR (75 MHz, CDCl 3, ppm): δ 109.8, 116.3, 123.5, 139.1, 152.2, thiophenecarbonitrile: 1 H NMR (400 MHz, CDCl 3, ppm): δ 7.75 (s, 3H). 13 C NMR (100 MHz, CDCl 3, S6
7 ppm): δ 109.2, 113.9, 127.3, 132.4, benzaldehyde: 1 H NMR (400 MHz, CDCl 3, ppm): δ 7.50 (t, J = 8.0Hz, 2H), 7.60 (t, J = 8.0Hz, 1H), 7.86 (d, J = 8.0Hz, 2H), 9.99 (s, 1H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 129.1, 129.8, 134.6, 136.5, methylbenzaldehyde: 1 H NMR (400 MHz, CDCl 3, ppm): δ 2.66 (s, 3H), 7.25 (d, J = 8.0Hz, 1H), 7.35 (t, J = 8.0Hz, 1H), 7.47 (t, J = 8.0Hz, 1H), 7.79 (d, J = 8.0Hz, 1H), (s, 1H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 19.9, 126.3, 131.8, 132.1, 133.7, 134.2, 140.6, methylbenzaldehyde: 1 H NMR (400 MHz, CDCl 3, ppm): δ 2.41 (s, 3H), 7.39 (t, J = 8.0Hz, 2H), 7.66 (s, 2H), 9.96 (s, 1H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 21.2, 127.2, 128.9, 130.0, 135.3, 136.5, 138.9, methylbenzaldehyde: 1 H NMR (400 MHz, CDCl 3, ppm): δ 2.44 (s, 3H), 7.33 (d, J = 8.0Hz, 2H), 7.77 (t, J = 8.0Hz, 2H), 9.96 (s, 1H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 21.2, 71.8, 127.9, 129.1, 135.3, methoxybenzaldehyde: 1 H NMR (400 MHz, CDCl 3, ppm): δ 3.89 (s, 3H), (m, 2H), 7.53 (t, J = 8.0Hz, 1H), 7.80 (d, J = 8.0Hz, 1H), (s, 1H). 13 C NMR (125 MHz, CDCl 3, ppm): δ 55.3, 111.4, 120.3, 124.5, 128.0, 135.7, 161.5, methoxybenzaldehyde: 1 H NMR (400 MHz, CDCl 3, ppm): δ 3.06 (s, 3H), (m, 1H), (m, 3H), 9.94 (s, 1H). 13 C NMR (125 MHz, CDCl 3, ppm): δ 55.3, 112.0, 121.3, 123.3, 129.9, 137.7, 160.0, methoxybenzaldehyde: 1 H NMR (400 MHz, CDCl 3, ppm): δ 3.73 (s, 3H), 6.86 (d, J = 12.0Hz, 2H), 7.69 (d, J = 12.0Hz, 2H), 9.73 (s, 1H). 13 C NMR (125 MHz, CDCl 3, ppm): δ 55.2, 114.0, 129.6, 131.6, 164.2, chlorobenzoic aldehyde: 1 H NMR (400 MHz, CDCl 3, ppm): δ 7.53 (d, J = 12.0Hz, 2H), 7.83 (d, J = 12.0Hz, 2H), 9.99 (s, 1H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 129.5, 130.9, 134.7, 141.0, nitrobenzaldehyde: 1 H NMR (400 MHz, CDCl 3, ppm): δ 8.09 (d, J = 8.0Hz, 2H), 8.41 (d, J = 12.0Hz, 2H), 10.17(s, 1H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 124.3, 130.5, 140.1, 151.1, pyridinecarboxaldehyde: 1 H NMR (400 MHz, CDCl 3, ppm): δ (m, 1H), 8.20 (d, J = 8.0Hz, 1H), 8.87 (d, J = 8.0Hz, 1H), 9.11 (d, J = 4.0Hz, 1H), (s, 1H). 13 C NMR (100 MHz, CDCl 3, ppm): δ 124.0, 131.3, 135.7, 151.7, 154.5, thenaldehyde: 1 H NMR (400 MHz, CDCl 3, ppm): δ (m, 1H), (m, 2H), 9.96 (d, J = 4.0Hz, 1H). 13 C NMR (125 MHz, CDCl 3, ppm): δ 128.2, 134.9, 136.3, 143.7, S7
8 The 1 H and 13 C NMR spectra of 1-(6-(1H-pyrazol-1-yl)pyridin-2-yl)ethanone S8
9 The 1 H and 13 C NMR spectra of 1-(6-(1H-pyrazol-1-yl)pyridin-2-yl)-3-(dimethylamino)prop-2-en-1-one S9
10 The 1 H and 13 C NMR spectra of 2-(1H-pyrazol-1-yl)-6-(1H-pyrazol-3-yl)pyridine f1 (ppm) S10
11 The 1 H and 13 C NMR spectra of the product benzonitrile S11
12 The 1 H and 13 C NMR spectra of the product 2-methylbenzonitrile S12
13 The 1 H and 13 C NMR spectra of the product 3-methylbenzonitrile S13
14 The 1 H and 13 C NMR spectra of the product 4-methylbenzonitrile S14
15 The 1 H and 13 C NMR spectra of the product 2-methoxybenzonitrile S15
16 The 1 H and 13 C NMR spectra of the product 3-methoxybenzonitrile S16
17 The 1 H and 13 C NMR spectra of the product 4-methoxybenzonitrile S17
18 The 1 H and 13 C NMR spectra of the product 4-chlorobenzonitrile S18
19 The 1 H and 13 C NMR spectra of the product 4-nitrobenzonitrile S19
20 The 1 H and 13 C NMR spectra of the product 1-naphthonitrile S20
21 The 1 H and 13 C NMR spectra of the product 3,4-(methylenedioxy)benzonitrile S21
22 The 1 H and 13 C NMR spectra of the product 3-cyanopyridine S22
23 The 1 H and 13 C NMR spectra of the product 2-thiophenecarbonitrile 氰基噻吩 - 碳谱 f1 (ppm) S23
24 The 1 H and 13 C NMR spectra of the product benzaldehyde tdw-2-c400 13C OBSERVE f1 (ppm) S24
25 The 1 H and 13 C NMR spectra of the product 2-methylbenzaldehyde 邻甲基苯甲醛 - 碳谱 f1 (ppm) S25
26 The 1 H and 13 C NMR spectra of the product 3-methylbenzaldehyde S26
27 The 1 H and 13 C NMR spectra of the product 4-methylbenzaldehyde S27
28 The 1 H and 13 C NMR spectra of the product 2-methoxybenzaldehyde S28
29 The 1 H and 13 C NMR spectra of the product 3-methoxybenzaldehyde CARBON_ f1 (ppm) S29
30 The 1 H and 13 C NMR spectra of the product 4-methoxybenzaldehyde CARBON_ f1 (ppm) S30
31 The 1 H and 13 C NMR spectra of the product 4-chlorobenzoic aldehyde S31
32 The 1 H and 13 C NMR spectra of the product 4-nitrobenzaldehyde S32
33 The 1 H and 13 C NMR spectra of the product 3-pyridinecarboxaldehyde S33
34 The 1 H and 13 C NMR spectra of the product 2-thenaldehyde S34
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