An Expedient Pd/DBU Mediated Cyanation of Aryl/Heteroaryl ... · An Expedient Pd/DBU Mediated...
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An Expedient Pd/DBU Mediated Cyanation of
Aryl/Heteroaryl Bromides With K4[Fe(CN)6]
Dengyou Zhang, Haifeng Sun, Lei Zhang, Yu Zhou, Chunpu Li, Hualiang Jiang,
Kaixian Chen, and Hong Liu*
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica,
Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai
201203, P. R. China
Table of Contents
General information .................................................................................................. S1
General procedure for palladium catalyzed cyanation .......................................... S1
Characterization data of aryl/heteroaryl nitriles .............................................. S2-S9
NMR spectra of isolated aryl/heteroaryl nitriles .......................................... S10-S59
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General information
Unless otherwise noted, the reagents (chemicals) were purchased from commercial
sources, and used without further purification. Water was deionized before used.
Analytical thin layer chromatography (TLC) was HSGF 254 (0.15-0.2 mm thickness).
Compound spots were visualized by UV light (254 nm). Column chromatography was
performed on silica gel FCP 200-300. NMR spectra were run on 300 or 400 MHz
instrument. Chemical shifts were reported in parts per million (ppm, δ) downfield
from tetramethylsilane. Proton coupling patterns are described as singlet (s), doublet
(d), triplet (t), quartet (q), multiplet (m), and broad (br). Low- and high-resolution
mass spectra (LRMS and HRMS) were measured on spectrometer.
General procedure for palladium catalyzed cyanation of
aryl/heteroaryl bromides
A vial equipped with a magnetic stir bar was charged with Pd(PPh3)4 (1-5% mmol),
K4[Fe(CN)6].3H2O (0.4 mmol), aryl/heteroaryl bromides (1.0 mmol, if solid) and
capped with septa. The vial was evacuated and backfilled with argon and the process
was repeated three times. Under argon, aryl/heteroaryl bromides (1.0 mmol, if liquid),
t-BuOH/H2O (1:1) 3.0 mL and DBU (0.25 mmol) were charged successively to the
vial via syringe, and then the resulting mixture was stirred at room temperature for 10
min. After that, the vial was kept in the pre-heated 85 °C oil bath for appropriate time.
After the reaction was complete, the reaction mixture was cooled to room temperature
and filtered. The cake was rinsed with methanol followed by dichloromethane. The
filtrate obtained was concentrated in vacuum. The crude product was purified by
silica gel column chromatography.
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Characterization data of aryl/heteroaryl nitriles
2-Amino-5-cyanopyridine:
1H NMR (400 MHz, DMSO-d6) δ 8.31 (d, J = 2.0 Hz, 1H), 7.67 (d, J = 8.8 Hz, 1H),
7.03 (s, 2H), 6.48 (d, J = 8.8 Hz, 1H); 13C NMR (100 MHz, DMSO-d6) δ 161.56,
153.21, 139.34, 119.01, 107.78, 94.62. EI-MS m/z (M+) 119; EI-HRMS calcd for (M+)
119.0483, found 119.0480.
2-Methylamino-5-cyanopyridine:
1H NMR (400 MHz, DMSO-d6) δ 8.39 (d, J = 2.0 Hz, 1H), 7.65 (s, 1H), 7.55 (s, 1H),
6.51 (d, J = 8.8 Hz, 1H), 2.81 (d, J = 4.8 Hz, 3H). 13C NMR (100 MHz, DMSO-d6) δ
160.47, 153.16, 138.23, 119.14, 108.93, 94.18, 27.56. EI-MS m/z (M+) 133;
EI-HRMS calcd for (M+) 133.0640, found 133.0636.
2-(Pyrrolidin-1-yl)-5-cyanopyridine:
1H NMR (400 MHz, CDCl3) δ 8.39 (d, J = 2.4 Hz, 1H), 7.55 (dd, J = 2.4, 8.8 Hz, 1H),
6.32 (d, J = 8.8 Hz, 1H), 3.48 (br, 4H), 2.03 (s, 4H); 13C NMR (100 MHz, CDCl3) δ
157.71, 153.27, 139.17, 119.44, 106.37, 95.08, 47.10, 25.56. EI-MS m/z (M+) 173;
EI-HRMS calcd for (M+) 173.0953, found 173.0950.
tert-Butyl 4-(5-Cyanopyridin-2-yl)piperazine-1-carboxylate:
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1H NMR (400 MHz, CDCl3) δ 8.40 (d, J = 2.4 Hz, 1H), 7.62 (dd, J = 2.4, 8.8 Hz, 1H),
6.59 (d, J = 8.8 Hz, 1H), 3.71-3.62 (m, 4H), 3.58-3.49 (m, 4H), 1.48 (s, 9H); 13C
NMR (100 MHz, CDCl3) δ 159.36, 154.80, 152.80, 140.13, 118.67, 105.96, 96.91,
80.49, 44.35, 28.57. EI-MS m/z (M+) 288; EI-HRMS calcd for (M+) 288.1586, found
288.1582.
2-(4-Morpholinyl)-5-cyanopyridine:
1H NMR (400 MHz, DMSO-d6) δ 8.50 (d, J = 2.4 Hz, 1H), 7.87 (dd, J = 2.4, 9.2 Hz,
1H), 6.93 (d, J = 9.2 Hz, 1H), 3.70-3.65 (m, 4H), 3.64-3.59 (m, 4H). 13C NMR (100
MHz, CDCl3) δ 159.69, 152.80, 140.11, 118.66, 105.83, 97.16, 66.66, 44.88. EI-MS
m/z (M+) 189; EI-HRMS calcd for (M+) 189.0902, found 189.0904.
3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carbonitrile:
1H NMR (400 MHz, DMSO-d6) δ 7.98 (d, J = 2.0 Hz, 1H), 7.93 (s, 1H), 7.28 (d, J =
1.0 Hz, 1H), 4.11 (t, J = 4.4 Hz, 2H), 3.48-3.45 (m, 2H); 13C NMR (100 MHz,
DMSO-d6) δ 150.48, 145.40, 137.39, 121.55, 118.52, 94.77, 63.46, 39.55. EI-MS m/z
(M+) 161; EI-HRMS calcd for (M+) 161.0589, found 161.0594.
3,4-Dihydro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile:
1H NMR (400 MHz, DMSO-d6) δ 8.09 (d, J = 2.0 Hz, 1H), 7.62 (s, 2H), 7.45 (d, J =
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2.0 Hz, 1H), 3.57 (t, J = 8.8 Hz, 2H), 3.01 (t, J = 8.8 Hz, 2H). 13C NMR (100 MHz,
DMSO-d6) δ 166.06, 152.36, 131.42, 122.90, 119.47, 94.53, 43.13, 26.05. EI-MS m/z
(M+) 145; EI-HRMS calcd for (M+) 145.0640, found 145.0634.
2-Amino-5-cyano-6-methylpyridine:
1H NMR (400 MHz, CDCl3) δ 7.55 (d, J=8.4 Hz, 1H), 6.33 (d, J=8.4 Hz, 1H), 4.99 (s,
2H), 2.56 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 162.53, 159.68, 141.32, 118.65,
105.66, 97.56, 23.57. EI-MS m/z (M+) 133; EI-HRMS calcd for (M+) 133.0640, found
133.0639.
2-Amino-5-cyano-3-trifluoromethylpyridine:
1H NMR (400 MHz, DMSO-d6) δ 8.59 (d, J = 2.0 Hz, 1H), 8.24 (s, 1H), 7.57 (s, 2H).
13C NMR (100 MHz, DMSO-d6) δ 156.95, 156.51, 139.00, 124.50, 121.80, 117.54,
106.20, 105.88, 105.56, 105.24, 94.70. EI-MS m/z (M+) 187; EI-HRMS calcd for (M+)
187.0357, found 187.0357.
2-Amino-5-cyano-3-fluoropyridine:
1H NMR (300 MHz, DMSO-d6) δ 8.22-8.19 (m, 1H), 7.83 (dd, J = 1.8, 11.4 Hz, 1H),
7.37 (s, 2H). 13C NMR (100 MHz, DMSO-d6) δ 152.50, 152.38, 148.90, 148.85,
145.43, 142.90, 122.79, 122.61, 117.68, 94.33. EI-MS m/z (M+) 137; EI-HRMS calcd
for (M+) 137.0389, found 137.0387.
2-Amino-3-chloro-5-cyanopyridine:
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1H NMR (400 MHz, DMSO-d6) δ 8.33 (d, J = 1.8 Hz, 1H), 8.07 (d, J = 1.8 Hz, 1H),
7.41 (s, 2H). 13C NMR (100 MHz, DMSO-d6) δ 157.86, 151.40, 138.63, 117.53,
112.64, 95.83. EI-MS m/z (M+) 153; EI-HRMS calcd for (M+) 153.0094, found
153.0086.
2-Amino-3-cyanopyridine:
1H NMR (400 MHz, DMSO-d6) δ 8.19 (dd, J = 2.0, 4.8 Hz, 1H), 7.85 (dd, J = 2.0, 7.6
Hz, 1H), 6.87 (s, 2H), 6.63 (dd, J = 4.8, 7.6 Hz, 1H). 13C NMR (100 MHz, DMSO-d6)
δ 159.94, 153.18, 142.22, 117.02, 111.91, 89.15. EI-MS m/z (M+) 119; EI-HRMS
calcd for (M+) 119.0483, found 119.0491.
2-Amino-3-cyano-5-methylpyridine
1H NMR (400 MHz, DMSO-d6) δ 8.05 (d, J = 2.0 Hz, 1H), 7.68 (d, J = 2.0 Hz, 1H),
6.62 (s, 2H), 2.10 (s, 3H). 13C NMR (101 MHz, cdcl3) δ 158.32, 153.32, 141.84,
120.60, 117.15, 88.78, 16.36. EI-MS m/z (M+) 133; EI-HRMS calcd for (M+)
133.0640, found 133.0639.
2-Amino-3-cyano-5-fluoropyridine:
1H NMR (400 MHz, DMSO-d6) δ 8.26 (d, J=3.2, 1H), 7.98 (dd, J = 3.2, 8.4 Hz, 1H),
6.86 (s, 2H). 13C NMR (100 MHz, DMSO-d6) δ 157.41, 151.72, 149.33, 141.50,
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141.25, 128.74, 128.52, 115.90, 88.69, 88.64. EI-MS m/z (M+) 137; EI-HRMS calcd
for (M+) 137.0389, found 137.0394.
Piperonylnitrile:
1H NMR (400 MHz, DMSO-d6) δ 7.46-7.36 (m, 2H), 7.10 (d, J = 8.0 Hz, 1H), 6.17 (s,
2H). 13C NMR (100 MHz, DMSO-d6) δ 151.44, 147.81, 128.52, 118.90, 111.30,
109.35, 103.76, 102.47. EI-MS m/z (M+) 147; EI-HRMS calcd for (M+) 147.0320,
found 147.0308.
4-Methoxybenzonitrile:
1H NMR (400 MHz, CDCl3) δ 7.57 (d, J = 8.8 Hz, 2H), 6.94 (d, J = 8.8 Hz, 2H), 3.85
(s, 3H); 13C NMR (125 MHz, CDCl3) δ 163.00, 134.13, 119.40, 114.91, 104.08, 55.71.
EI-MS m/z (M+) 133; EI-HRMS calcd for (M+) 133.0528, found 133.0518.
tert-Butyl 4-(2-(4-Cyanophenoxy)acetyl)piperazine-1-carboxylate:
O CN
N
O
BocN 1H NMR (400 MHz, DMSO-d6) δ 7.75 (d, J = 8.8 Hz, 2H), 7.08 (d, J = 8.8 Hz, 2H),
5.00 (s, 2H), 3.45 -3.31 (m, 8H), 1.41 (s, 9H). 13C NMR (100 MHz, DMSO-d6) δ
165.31, 161.62, 153.79, 133.99, 119.12, 115.76, 103.02, 79.21, 65.67, 43.75, 41.04,
28.02. EI-MS m/z (M+) 345; EI-HRMS calcd for (M+) 345.1689, found 345.1697.
4-Aminobenzonitrile:
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1H NMR (400 MHz, DMSO-d6) δ 7.38 (d, J = 8.4 Hz, 2H), 6.60 (d, J = 8.4 Hz, 2H),
6.13 (s, 2H). 13C NMR (100 MHz, DMSO-d6) δ 153.01, 133.45, 120.69, 113.44, 95.51.
EI-MS m/z (M+) 118; EI-HRMS calcd for (M+) 118.0531, found 118.0523.
3-Acetylbenzonitrile:
1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 8.17 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 7.6
Hz, 1H), 7.63-7.59 (m, 1H), 2.64 (s, 3H); 13C NMR (125 MHz, CDCl3) δ 196.01,
137.91, 136.19, 132.40, 132.21, 129.88, 118.11, 113.36, 26.77. EI-MS m/z (M+) 145;
EI-HRMS calcd for (M+) 145.0528, found 145.0528.
4-Acetylbenzonitrile:
1H NMR (400 MHz, DMSO-d6) δ 8.10 (d, J = 8.0 Hz, 2H), 8.01 (d, J = 8.0 Hz, 2H),
2.64 (s, 3H). 13C NMR (100 MHz, DMSO-d6) δ 197.35, 139.84, 132.76, 128.76,
118.17, 115.13, 27.01. EI-MS m/z (M+) 145; EI-HRMS calcd for (M+) 145.0528,
found 145.0529.
2-Naphthonitrile:
1H NMR (400 MHz, DMSO-d6) δ 8.58 (s, 1H), 8.11 (d, J = 8.4 Hz, 1H), 8.06 (t, J =
7.2 Hz, 2H), 7.78 (dd, J = 1.6, 8.4 Hz, 1H), 7.76-7.66 (m, 2H). 13C NMR (100 MHz,
DMSO-d6) δ 134.35, 134.27, 131.86, 129.33, 129.29, 128.48, 128.00, 127.75, 126.30,
119.17, 108.39. EI-MS m/z (M+) 153; EI-HRMS calcd for (M+) 153.0578, found
153.0587.
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1H-indole-5-carbonitrile:
NH
CN
1H NMR (400 MHz, DMSO-d6) δ 11.66 (s, 1H), 8.08 (s, 1H), 7.57-7.55 (m, 2H), 7.42
(dd, J = 1.6, 8.4 Hz, 1H), 6.58 (s, 1H). 13C NMR (100 MHz, DMSO-d6) δ 137.61,
128.10, 127.42, 125.74, 123.67, 120.82, 112.68, 102.10, 100.90. EI-MS m/z (M+) 142;
EI-HRMS calcd for (M+) 142.0531, found 142.0533.
Benzo[b]thiophene-3-carbonitrile:
1H NMR (300 MHz, DMSO-d6) δ 8.92 (s, 1H), 8.22 (dd, J = 1.2, 6.9 Hz, 1H), 7.95 (d,
J = 7.2 Hz, 1H), 7.66-7.54 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 138.69, 137.75,
137.46, 126.39, 126.18, 123.04, 122.74, 114.54, 107.32. EI-MS m/z (M+) 159;
EI-HRMS calcd for (M+) 159.0143, found 159.0152.
tert-butyl 4-(4-cyano-1H-pyrazol-1-yl)piperidine-1-carboxylate:
1H NMR (400 MHz, CDCl3) δ 7.83 (s, 1H), 7.81 (s, 1H), 4.36-4.22 (m, 3H), 2.89 (t, J
= 12.4 Hz, 2H), 2.17-2.10 (m, 2H), 1.95-1.84 (m, 2H), 1.47 (s, 9H). 13C NMR (100
MHz, CDCl3) δ 154.63, 142.28, 132.15, 113.62, 92.30, 80.38, 60.43, 42.67, 32.30,
28.58. EI-MS m/z (M+) 276; EI-HRMS calcd for (M+) 276.1586, found 276.1597.
Quinoline-6-carbonitrile:
1H NMR (300 MHz, DMSO-d6) δ 9.07 (dd, J = 1.8, 4.2 Hz, 1H), 8.66 (d, J = 1.2 Hz,
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1H), 8.49 (d, J = 8.4 Hz, 1H), 8.16 (d, J =8.4 Hz, 1H), 8.04 (dd, J = 1.8, 8.7 Hz, 1H),
7.69 (dd, J = 4.2, 8.4 Hz, 1H). 13C NMR (101 MHz, cdcl3) δ 153.69, 148.50, 136.75,
135.04, 130.44, 130.16, 127.29, 123.07, 118.64, 109.11. EI-MS m/z (M+) 154;
EI-HRMS calcd for (M+) 154.0531, found 154.0525.
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NMR spectra of isolated aryl/heteroaryl nitriles
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010203040506070809010011012013014015016017080
DMSO-d6 BB+DEPT-135
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27.5
60
38.8
8439
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39.3
0139
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39.7
1939
.927
40.1
36
94.1
77
108.
926
119.
142
138.
231
153.
157
160.
474
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S19
44.8
79
66.6
55
76.9
1277
.230
77.5
48
97.1
60
105.
828
118.
664
140.
112
152.
800
159.
691
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S20
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S21
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S22
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S23
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S24
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S25
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S26
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S27
010203040506070809010011012013014015016017080
DMSO-d6 BB+DEPT-135
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S28
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S29
010203040506070809010011012013014015016017080
DMSO-d6 BB+DEPT-135
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S30
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S31
010203040506070809010011012013014015016017080
DMSO-d6 BB+DEPT-135
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S32
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S33
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S34
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S35
16.3
58
38.8
8439
.092
39.3
0139
.510
39.7
1939
.927
40.1
36
88.7
78
117.
152
120.
603
141.
842
153.
323
158.
321
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S36
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S37
38.8
8439
.092
39.3
0139
.510
39.7
1839
.927
40.1
37
88.6
3788
.691
115.
904
128.
518
128.
744
141.
252
141.
495
149.
334
151.
723
157.
409
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S38
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S39
010203040506070809010011012013014015016017080
DMSO-d6 BB+DEPT-135
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S40
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S41
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S42
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S43
28.0
2538
.884
39.0
9239
.301
39.5
1039
.719
39.9
2840
.141
41.0
3743
.752
65.6
69
79.2
13
103.
021
115.
763
119.
122
133.
989
153.
793
161.
621
165.
306
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S44
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S45
38.8
8339
.093
39.3
0139
.510
39.7
1839
.928
40.1
38
95.5
05
113.
439
120.
694
133.
449
153.
009
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S46
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S47
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S48
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S49
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S50
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S51
38.8
8439
.092
39.3
0139
.510
39.7
1939
.928
40.1
35
108.
394
119.
175
126.
301
127.
752
128.
004
128.
481
129.
290
129.
328
131.
858
134.
275
134.
349
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S52
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S53
38.8
8639
.093
39.3
0139
.510
39.7
1939
.927
40.1
37
100.
902
102.
097
112.
680
120.
816
123.
667
125.
738
127.
421
128.
099
137.
609
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S54
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S55
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S56
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S57
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S58
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012
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S59
38.8
8539
.093
39.3
0139
.510
39.7
1939
.928
40.1
36
109.
115
118.
639
123.
072
127.
293
130.
165
130.
445
135.
037
136.
752
148.
499
153.
690
Electronic Supplementary Material (ESI) for Chemical CommunicationsThis journal is © The Royal Society of Chemistry 2012