NMR Chemical Shifts of Trace Impurities - Amazon S3

SI 1

NMR Chemical Shifts of Trace Impurities:

Industrially Preferred Solvents Used in Process and

Green Chemistry

Nicholas R. Babij‡, Elizabeth O. McCusker

‡, Gregory T. Whiteker*, Belgin Canturk, Nakyen

Choy, Lawrence C. Creemer, Carl V. De Amicis, Nicole M. Hewlett, Peter L. Johnson, James A.

Knobelsdorf, Fangzheng Li, Beth A. Lorsbach, Benjamin M. Nugent, Sarah J. Ryan, Michelle R.

Smith, and Qiang Yang

Process Chemistry, Dow AgroSciences, 9330 Zionsville Rd., Indianapolis, IN USA 46268

Supporting Information

Instrumental Details

NMR spectra were obtained using a Bruker AVANCE 400 MHz spectrometer. Data were

collected at ambient temperature and varied by ±2 °C. 1H NMR spectra were obtained at 400.13

MHz (number of scans = 16; acquisition time = 4 sec; 30 degree pulse width; relaxation delay =

1 sec; 32k data points; digital resolution = 0.25 Hz/pt; spectral badwidth = 16 to -4 ppm).

13C{

1H} NMR spectra were obtained at 100.62 MHz (number of scans = 512; acquisition time =

1.4 sec; 30 degree pulse width; relaxation delay = 1.3 sec; 32k data points; digital resolution =

SI 2

0.73 Hz/pt; spectral bandwidth = 220 to -20 ppm) using WALTZ-16 composite pulse

decoupling.

Corrections and Additions: The following chemical shifts have been revised from those reported

by Gottlieb, Kotlyar, and Nudelman (J. Org. Chem. 1997, 62, 7512): The 1H NMR chemical

shift for tert-butanol (CH3) in CD3OD was originally misassigned and has been corrected in the

tables found within this manuscript (1.22 ppm). The 13

C NMR chemical shift of pyridine (CH

[3,5]) in CD3CN was misreported and has been revised (124.77 ppm). 1H NMR resonances for

ethylene glycol (OH) and iso-propanol (OH) were observed in several deuterated solvents and

are reported accordingly.

SI 3

Table S1. 1H NMR data by chemical shifts (ppm) in CDCl3

shift Solvent proton mult shift solvent proton mult

8.62-8.61 pyridine CH (2,6) m 2.17 acetone CH3 s

8.03 formic acid HCO s 2.14 methyl ethyl ketone CH3CO s 7.68 pyridine CH (4) tt, 7.6, 1.8 2.13 MIBK CH nonet, 6.8

7.38-7.28 benzyl alcohol CH m 2.12 MIBK CH3CO s 7.38-7.28 benzyl alcohol CH m 2.10 acetic acid CH3 s

7.36-7.22 chlorobenzene CH m 2.10 acetonitrile CH3 s 7.32-7.27 anisole CH (3,5) m 2.09 glycol diacetate CH3 s

7.30-7.26 pyridine CH (3,5) m 2.06 iso-butyl acetate CH3CO s

7.30-7.26 ethyl benzene CH (3,5) m 2.06 methyl acetate CH3CO s

7.28-7.24 toluene CH (3,5) m 2.05 iso-amyl acetate CH3CO s 7.23-7.15 ethyl benzene CH (2,6) m 2.05 n-butyl acetate CH3CO s

7.23-7.15 ethyl benzene CH (4) m 2.05 ethyl acetate CH3CO s 7.18-7.14 toluene CH (2,4,6) m 2.03-1.81 2-MeTHF Hc, HD, HE m

7.15 m-xylene CH (5) t, 7.5 2.02 iso-propyl acetate CH3CO s

7.14-7.09 p-cymene ArH m 2.00-1.94 DMPU CH2 m

7.14-7.08 o-xylene CH m 1.92 iso-butyl acetate CH nonet, 6.7 7.06 p-xylene CH s 1.87-1.84 tetrahydrofuran CH2 m

7.00-6.96 m-xylene CH (2,4,6) m 1.84-1.86 cyclohexanone CH2 (3,5) m 6.97-6.89 anisole CH (2,4,6) m 1.77 iso-butanol CH nonet, 6.6

5.30 dichloromethane CH2 s 1.74-1.50 CPME CH2 m

4.99 iso-propyl acetate CH sept, 6.3 1.72 iso-amyl alcohol CH nonet, 6.7

4.71 benzyl alcohol CH2 d, 5.9 1.71-1.73 cyclohexanone CH2 (4) m 4.30-4.22 L-ethyl lactate CH m 1.70-1.60 methyl cyclohexane CH2 m

4.27 glycol diacetate CH2 s 1.68 iso-amyl acetate CH nonet, 6.7 4.25 L-ethyl lactate CH2 q, 7.1 1.64 benzyl alcohol OH t, 5.9

4.12 ethyl acetate CH2CH3 q, 7 1.64-1.57 n-butyl acetate OCH2CH2 m

4.10 iso-amyl acetate OCH2 t, 6.8 1.60-1.52 n-butanol CH2CH2OH m

4.07 n-butyl acetate OCH2 t, 6.7 1.52 iso-amyl acetate CH2CH q, 6.9 4.03 iso-propanol CH sept, 6.1 1.49 TAME CH2 q, 7.5

3.94 2-MeTHF CH dp, 7.9, 6.1 1.47 iso-amyl alcohol CH2CH q, 6.8 3.89 2-MeTHF OCHAHB td, 7.7, 5.9 1.44-1.35 n-butanol CH2CH3 m

3.85 iso-butyl acetate CH2 d, 6.7 1.43-1.34 n-butyl acetate CH2CH3 m

3.82-3.78 CPME CH m 1.43 cyclohexane CH2 s

3.81 anisole OCH3 s 1.42 L-ethyl lactate CH3CH d, 6.9 3.79 dimethyl carbonate CH3 s 1.42 ethanol OH br s

3.76 ethylene glycol CH2 s 1.41 2-MeTHF HF ddt, 11.7, 8.8, 7.6 3.76-3.73 tetrahydrofuran CH2O m 1.39-1.06 methyl cyclohexane CH2, CH m

3.72 ethanol CH2 q, 7.0 1.32-1.24 n-heptane CH2 m

3.71 2-MeTHF OCHAHB td, 8.0, 6.3 1.31 L-ethyl lactate CH3CH2 t, 7.1

3.68 iso-amyl alcohol CH2OH t, 6.8 1.30 iso-butanol OH t, 5.5 3.67 methyl acetate OCH3 s 1.27 tert-butanol CH3 s

3.65 n-butanol CH2OH t, 6.7 1.26 ethyl acetate CH2CH3 t, 7 3.49 methanol CH3 s 1.24 ethanol CH3 t, 7.0

3.41 iso-butanol CH2 dd, 6.5, 5.5 1.24 p-cymene (CH3)2 d, 6.9 3.41 ETBE CH2 q, 7.0 1.24 ethyl benzene CH3 t, 7.6

3.28 CPME OCH3 s 1.23 iso-propyl acetate (CH3)2 d, 6.3 3.25-3.22 DMPU NCH2 m 1.23 2-MeTHF CH3 d, 6.1

3.22 MTBE OCH3 s 1.21 iso-propanol CH3 d, 6.1 3.18 TAME OCH3 s 1.20 n-butanol OH br s

3.05-3.02 sulfolane CH2SO2 m 1.20 ETBE (CH3)3 s 2.92 DMPU NCH3 s 1.19 MTBE CCH3 s

2.87 p-cymene CH(CH3)2 sept, 6.9 1.17 ETBE CH3 t, 7.0 2.79 L-ethyl lactate OH d, 5.5 1.13 TAME (CH3)2 s

2.65 ethyl benzene CH2 q, 7.6 1.06 methyl ethyl ketone CH2CH3 t, 7 2.62 dimethyl sulfoxide CH3 s 1.05 methanol OH br s

2.46 methyl ethyl ketone CH2 q, 7 0.94 n-butanol CH3 t, 7.3 2.36 toluene CH3 s 0.94 n-butyl acetate CH2CH3 t, 7.4

2.33 cyclohexanone CH2 (2,6) t, 7 0.93 iso-butyl acetate (CH3)2 d, 6.7 2.32 p-cymene Ar-CH3 s 0.92 iso-amyl acetate (CH3)2 d, 6.6

2.32 m-xylene CH3 s 0.92 iso-amyl alcohol CH3 d, 6.7 2.31 p-xylene CH3 s 0.92 iso-butanol CH3 d, 6.7

2.30 MIBK CH2 d, 7.0 0.92-0.82 methyl cyclohexane CH2 m 2.28 ethylene glycol OH br s 0.92 MIBK (CH3)2 d, 6.7

2.26 o-xylene CH3 s 0.88 n-heptane CH3 t, 6.8 2.25-2.21 sulfolane CH2 m 0.87 TAME CH2CH3 t, 7.5

2.23 acetic anhydride CH3 s 0.86 methyl cyclohexane CH3 d, 6.6

SI 4

Table S2.

13C NMR data by chemical shifts (ppm) in CDCl3

shift solvent carbon shift solvent carbon shift solvent carbon

212.57 cyclohexanone CO 74.77 TAME C 27.71 iso-butyl acetate CH

209.56 methyl ethyl ketone CO 72.87 MTBE C 27.64 ETBE (CH3)3

208.83 MIBK CO 72.56 ETBE C 27.00 cyclohexanone CH2 (3,5) 207.07 acetone CO 70.63 iso-butyl acetate CH2 26.99 MTBE CCH3

175.99 acetic acid CO 69.80 iso-butanol CH2 26.94 cyclohexane CH2 175.70 L-ethyl lactate CO 69.15 tert-butanol C 26.50 methyl cyclohexane CH2

172.15 iso-amyl acetate CO 68.00 tetrahydrofuran CH2O 26.40 methyl cyclohexane CH2

171.48 methyl acetate CO 67.72 2-MeTHF CH2O 25.92 2-MeTHF CH2CH2O

171.36 ethyl acetate CO 67.64 iso-propyl acetate CH 25.68 tetrahydrofuran CH2 171.20 n-butyl acetate CO 66.78 L-ethyl lactate CH 25.14 iso-propanol CH3

171.19 iso-butyl acetate CO 65.31 benzyl alcohol CH2 25.09 iso-amyl acetate CH 170.76 glycol diacetate CO 64.50 iso-propanol CH 24.97 cyclohexanone CH2 (4)

170.63 iso-propyl acetate CO 64.36 n-butyl acetate OCH2 24.74 iso-amyl alcohol CH

166.38 acetic anhydride CO 63.79 ethylene glycol CH2 24.66 MIBK CH

165.40 formic acid CO 63.56 iso-amyl acetate OCH2 24.50 TAME (CH3)2 159.59 anisole C (1) 62.76 n-butanol CH2OH 24.10 p-cymene (CH3)2

156.85 DMPU CO 62.21 glycol diacetate CH2 23.55 CPME CH2 (3,4) 156.45 dimethyl carbonate CO 61.63 L-ethyl lactate CH2 22.91 methyl cyclohexane CH3

149.90 pyridine CH (2,6) 61.36 iso-amyl alcohol CH2OH 22.79 sulfolane CH2

145.89 p-cymene C (4) 60.49 ethyl acetate CH2 22.71 n-heptane CH2 (2,6)

144.25 ethylbenzene C (1) 58.28 ethanol CH2 22.62 iso-amyl alcohol CH3 140.98 benzyl alcohol C (1) 56.79 ETBE CH2 22.55 MIBK (CH3)2

137.88 toluene C (1) 56.30 CPME CH3 22.45 iso-amyl acetate (CH3)2 137.78 m-xylene C (1,3) 55.14 anisole CH3 22.24 DMPU CH2

136.49 o-xylene C (1) 54.89 dimethyl carbonate CH3 22.15 acetic anhydride CH3 135.89 pyridine CH (4) 53.52 dichloromethane CH2 21.84 iso-propyl acetate (CH3)2

135.14 p-cymene C (1) 52.82 MIBK CH2 21.45 toluene CH3 134.67 p-xylene C (1,4) 51.58 methyl acetate OCH3 21.42 iso-propyl acetate CH3CO

134.29 chlorobenzene C (1) 51.16 sulfolane CH2SO2 21.33 m-xylene CH3 129.91 m-xylene CH (2) 50.41 methanol CH3 21.05 iso-amyl acetate CH3CO

129.71 chlorobenzene CH (3,5) 49.45 MTBE OCH3 21.04 ethyl acetate CH3CO 129.59 o-xylene CH (3,6) 49.04 TAME OCH3 20.99 n-butyl acetate CH3CO

129.44 anisole CH (3,5) 47.93 DMPU NCH2 20.97 2-MeTHF CH3 129.05 toluene CH (2,6) 41.97 cyclohexanone CH2 (2,6) 20.95 p-cymene Ar-CH3

128.98 p-cymene CH (2,6) 41.79 iso-amyl alcohol CH2CH 20.94 p-xylene CH3 128.92 p-xylene CH (2,3,5,6) 40.76 dimethyl sulfoxide CH3 20.93 iso-butyl acetate CH3CO

128.62 chlorobenzene CH (2,6) 37.29 iso-amyl acetate CH2CH 20.81 acetic acid CH3 128.54 benzyl alcohol CH (3,5) 36.89 methyl ethyl ketone CH2 20.80 glycol diacetate CH3

128.31 ethylbenzene CH (3,5) 35.67 DMPU CH3 20.67 methyl acetate CH3CO 128.24 toluene CH (3,5) 35.51 methyl cyclohexane CH2CH 20.41 L-ethyl lactate CH3CH

128.15 m-xylene CH (5) 34.91 n-butanol CH2CH2OH 19.71 o-xylene CH3 127.85 ethylbenzene CH (2,6) 33.70 p-cymene CH(CH3)2 19.16 n-butyl acetate CH2CH3

127.61 benzyl alcohol CH (4) 33.11 2-MeTHF CH2CH 19.08 iso-butyl acetate (CH3)2 126.98 benzyl alcohol CH (2,6) 32.79 methyl cyclohexane CH 18.92 n-butanol CH2CH3

126.43 chlorobenzene CH (4) 32.14 TAME CH2 18.86 iso-butanol CH3 126.28 p-cymene CH (3,5) 31.97 CPME CH2 (2,5) 18.41 ethanol CH3

126.04 m-xylene CH (4,6) 31.91 n-heptane CH2 (3,5) 16.35 ETBE CH3 125.79 o-xylene CH (4,5) 31.25 tert-butanol CH3 15.60 ethylbenzene CH3

125.58 ethylbenzene CH (4) 30.92 acetone CH3 14.19 ethyl acetate CH2CH3 125.31 toluene CH(4) 30.87 iso-butanol CH 14.18 L-ethyl lactate CH3CH2

123.71 pyridine CH (3,5) 30.70 n-butyl acetate OCH2CH2 14.11 n-heptane CH3 120.67 anisole CH (4) 30.34 MIBK CH3CO 13.86 n-butanol CH3

116.43 acetonitrile CN 29.49 methyl ethyl ketone CH3CO 13.71 n-butyl acetate CH2CH3 113.93 anisole CH (2,6) 29.04 n-heptane CH2 (4) 8.22 TAME CH2CH3

83.03 CPME CH 28.89 ethylbenzene CH2 7.86 methyl ethyl ketone CH2CH3 75.23 2-MeTHF CH

1.89 acetonitrile CH3

SI 5

Table S3. 1H NMR data by chemical shifts (ppm) in acetone-d6

shift solvent proton mult shift solvent proton mult

8.59-8.57 pyridine CH (2,6) m 2.27 m-xylene CH3 s 8.11 formic acid HCO s 2.26 p-xylene CH3 s

7.76 pyridine CH (4) tt, 7.6, 1.8 2.23 o-xylene CH3 s

7.42-7.31 chlorobenzene CH m 2.21 acetic anhydride CH3 s

7.37-7.29 benzyl alcohol CH m 2.21-2.17 sulfolane CH2 m 7.36-7.33 pyridine CH (3,5) m 2.12-2.02 MIBK CH m

7.31-7.25 anisole CH (3,5) m 2.09 acetone CH3 s 7.29-7.25 ethyl benzene CH (3,5) m 2.07 methyl ethyl ketone CH3CO s

7.26-7.22 toluene CH (3,5) m 2.06 MIBK CH3CO s

7.25-7.20 benzyl alcohol CH m 2.05 acetonitrile CH3 s

7.22-7.19 ethyl benzene CH (2,6) m 2.01 glycol diacetate CH3 s 7.18-7.12 toluene CH (2,4,6) m 2.00-1.75 2-MeTHF Hc, HD, HE m

7.17-7.13 ethyl benzene CH (4) m 1.99 iso-butyl acetate CH3CO s 7.13-7.07 p-cymene ArH m 1.98 methyl acetate CH3CO s

7.12-7.03 o-xylene CH m 1.97 iso-amyl acetate CH3CO s

7.11 m-xylene CH (5) t, 7.5 1.97 n-butyl acetate CH3CO s

7.05 p-xylene CH s 1.97-1.92 DMPU CH2 m 6.99-6.94 m-xylene CH (2,4,6) m 1.97 ethyl acetate CH3CO s

6.96-6.89 anisole CH (2,4,6) m 1.96 acetic acid CH3 s 5.63 dichloromethane CH2 s 1.94 iso-propyl acetate CH3CO s

4.91 iso-propyl acetate CH sept, 6.3 1.89 iso-butyl acetate CH nonet, 6.7 4.63 benzyl alcohol CH2 d, 5.9 1.81-1.77 tetrahydrofuran CH2 m

4.24-4.09 L-ethyl lactate CH m 1.79-1.83 cyclohexanone CH2 (3,5) m 4.24-4.09 L-ethyl lactate CH2 m 1.73 iso-amyl alcohol CH nonet, 6.7

4.24 glycol diacetate CH2 s 1.72-1.44 CPME CH2 m 4.16 benzyl alcohol OH t, 5.9 1.70-1.74 cyclohexanone CH2 (4) m

4.05 iso-amyl acetate OCH2 t, 6.8 1.70-1.59 methyl cyclohexane CH2 m 4.05 ethyl acetate CH2CH3 q, 7 1.69 iso-amyl acetate CH nonet, 6.7

4.02 n-butyl acetate OCH2 t, 6.7 1.68 iso-butanol CH nonet, 6.6 3.95-3.84 iso-propanol CH m 1.62-1.55 n-butyl acetate OCH2CH2 m

3.83 2-MeTHF CH dp, 7.9, 6.1 1.51-1.44 n-butanol CH2CH2OH m 3.81 iso-butyl acetate CH2 d, 6.7 1.50 iso-amyl acetate CH2CH q, 6.9

3.78 anisole OCH3 s 1.46 TAME CH2 q, 7.5 3.78 2-MeTHF OCHAHB td, 7.7, 5.9 1.43 cyclohexane CH2 s

3.77-3.73 CPME CH m 1.42-1.33 n-butyl acetate CH2CH3 m 3.72 dimethyl carbonate CH3 s 1.41-1.32 n-butanol CH2CH3 m

3.64-3.61 tetrahydrofuran CH2O m 1.39 iso-amyl alcohol CH2CH q, 6.8 3.59 methyl acetate OCH3 s 1.39-1.07 methyl cyclohexane CH2, CH m

3.58-3.54 ethylene glycol CH2 m 1.34 2-MeTHF HF ddt, 11.7, 8.8, 7.6 3.58 2-MeTHF OCHAHB td, 8.0, 6.3 1.33-1.25 n-heptane CH2 m

3.57 ethanol CH2 qd, 7.0, 5.2 1.32 L-ethyl lactate CH3CH d, 6.9 3.56 iso-amyl alcohol CH2OH td, 6.8, 5.2 1.23 L-ethyl lactate CH3CH2 t, 7.1

3.53 n-butanol CH2OH td, 6.5, 5.3 1.20 p-cymene (CH3)2 d, 6.9 3.45 iso-butanol OH t, 5.5 1.20 ethyl acetate CH2CH3 t, 7

3.39 ethanol OH t, 5.2 1.20 ethyl benzene CH3 t, 7.6 3.39 iso-propanol OH d, 4.3 1.19 iso-propyl acetate (CH3)2 d, 6.3

3.37 ETBE CH2 q, 7.0 1.18 tert-butanol CH3 s 3.35 n-butanol OH t, 5.3 1.14 ETBE (CH3)3 s

3.34 iso-amyl alcohol OH t, 5.2 1.14 2-MeTHF CH3 d, 6.1 3.31 methanol CH3 d, 5.3 1.13 MTBE CCH3 s

3.29 iso-butanol CH2 dd, 6.5, 5.5 1.12 ethanol CH3 t, 7.0 3.22 tert-butanol OH s 1.10 iso-propanol CH3 d, 6.1

3.19 CPME OCH3 s 1.07 TAME (CH3)2 s 3.13 MTBE OCH3 s 1.06 ETBE CH3 t, 7.0

3.12 methanol OH q, 5.3 0.96 methyl ethyl ketone CH2CH3 t, 7 3.10 TAME OCH3 s 0.93-0.83 methyl cyclohexane CH2 m

2.97-2.93 sulfolane CH2SO2 m 0.92 n-butyl acetate CH2CH3 t, 7.4 2.85 p-cymene CH(CH3)2 sept, 6.9 0.91 iso-amyl acetate (CH3)2 d, 6.6

2.81 DMPU NCH3 s 0.91 iso-butyl acetate (CH3)2 d, 6.7 2.63 ethyl benzene CH2 q, 7.6 0.90 n-butanol CH3 t, 7.3

2.52 dimethyl sulfoxide CH3 s 0.89 iso-amyl alcohol CH3 d, 6.7

2.45 methyl ethyl ketone CH2 q, 7 0.88 n-heptane CH3 t, 6.8

2.31 MIBK CH2 d, 7.0 0.88 MIBK (CH3)2 d, 6.7 2.31 toluene CH3 s 0.87 iso-butanol CH3 d, 6.7

2.27 cyclohexanone CH2 (2,6) t, 7 0.85 methyl cyclohexane CH3 d, 6.6 2.27 p-cymene Ar-CH3 s 0.82 TAME CH2CH3 t, 7.5

SI 6

Table S4. 13

C NMR data by chemical shifts (ppm) in acetone-d6

shift solvent Carbon shift solvent carbon shift solvent carbon


208.30 methyl ethyl ketone CO 72.81 MTBE C 27.86 ETBE (CH3)3 207.75 MIBK CO 72.57 ETBE C 27.68 cyclohexanone CH2 (3,5)

205.87 acetone CO 70.71 iso-butyl acetate CH2 27.51 cyclohexane CH2 175.57 L-ethyl lactate CO 69.46 iso-butanol CH2 27.24 MTBE CCH3

172.31 acetic acid CO 68.16 tert-butanol C 27.09 methyl cyclohexane CH2 171.29 methyl acetate CO 68.07 tetrahydrofuran CH2O 26.97 methyl cyclohexane CH2

171.02 iso-amyl acetate CO 67.87 2-MeTHF CH2O 26.47 2-MeTHF CH2CH2O

170.96 ethyl acetate CO 67.74 iso-propyl acetate CH 26.19 tetrahydrofuran CH2

170.94 n-butyl acetate CO 67.43 L-ethyl lactate CH 25.77 iso-amyl acetate CH 170.89 iso-butyl acetate CO 64.68 benzyl alcohol CH2 25.77 iso-propanol CH3

170.84 glycol diacetate CO 64.44 n-butyl acetate OCH2 25.59 cyclohexanone CH2 (4) 170.38 iso-propyl acetate CO 64.28 ethylene glycol CH2 25.43 iso-amyl alcohol CH

167.44 acetic anhydride CO 63.74 iso-propanol CH 25.05 MIBK CH

162.29 formic acid CO 63.23 iso-amyl acetate OCH2 24.73 TAME (CH3)2

160.71 anisole C (1) 62.81 glycol diacetate CH2 24.40 p-cymene (CH3)2 157.04 dimethyl carbonate CO 62.15 n-butanol CH2OH 24.14 CPME CH2 (3,4)

156.97 DMPU CO 61.17 L-ethyl lactate CH2 23.33 n-heptane CH2 (2,6) 150.67 pyridine CH (2,6) 60.72 iso-amyl alcohol CH2OH 23.31 sulfolane CH2

146.54 p-cymene C (4) 60.56 ethyl acetate CH2 23.16 methyl cyclohexane CH3

144.99 ethylbenzene C (1) 57.76 ethanol CH2 23.13 DMPU CH2

143.42 benzyl alcohol C (1) 57.06 ETBE CH2 22.98 iso-amyl alcohol CH3 138.49 toluene C (1) 56.18 CPME CH3 22.73 MIBK (CH3)2

138.34 m-xylene C (1,3) 55.34 anisole CH3 22.71 iso-amyl acetate (CH3)2 137.03 o-xylene C (1) 54.95 dichloromethane CH2 22.05 acetic anhydride CH3

136.57 pyridine CH (4) 54.95 dimethyl carbonate CH3 22.00 iso-propyl acetate (CH3)2

135.70 p-cymene C (1) 52.80 MIBK CH2 21.41 toluene CH3

135.27 p-xylene C (1,4) 51.60 sulfolane CH2SO2 21.32 m-xylene CH3 134.63 chlorobenzene C (1) 51.51 methyl acetate OCH3 21.29 2-MeTHF CH3

130.94 chlorobenzene CH (3,5) 49.81 methanol CH3 21.19 iso-propyl acetate CH3CO 130.52 m-xylene CH (2) 49.35 MTBE OCH3 20.94 p-cymene Ar-CH3

130.28 o-xylene CH (3,6) 48.96 TAME OCH3 20.94 p-xylene CH3

130.21 anisole CH (3,5) 48.57 DMPU NCH2 20.83 ethyl acetate CH3CO

129.75 toluene CH (2,6) 42.80 iso-amyl alcohol CH2CH 20.80 iso-amyl acetate CH3CO 129.71 p-cymene CH (2,6) 42.24 cyclohexanone CH2 (2,6) 20.78 L-ethyl lactate CH3CH

129.65 p-xylene CH (2,3,5,6) 41.23 dimethyl sulfoxide CH3 20.76 n-butyl acetate CH3CO 129.30 chlorobenzene CH (2,6) 38.18 iso-amyl acetate CH2CH 20.69 iso-butyl acetate CH3CO

129.12 ethylbenzene CH (3,5) 36.75 methyl ethyl ketone CH2 20.63 glycol diacetate CH3

129.03 toluene CH (3,5) 36.12 methyl cyclohexane CH2CH 20.51 acetic acid CH3

128.93 m-xylene CH (5) 35.93 n-butanol CH2CH2OH 20.45 methyl acetate CH3CO 128.92 benzyl alcohol CH (3,5) 35.60 DMPU CH3 19.77 n-butyl acetate CH2CH3

128.59 ethylbenzene CH (2,6) 34.40 p-cymene CH(CH3)2 19.72 n-butanol CH2CH3 127.65 chlorobenzene CH (4) 33.80 2-MeTHF CH2CH 19.68 o-xylene CH3

127.55 benzyl alcohol CH (4) 33.47 methyl cyclohexane CH 19.36 iso-butanol CH3 127.35 benzyl alcohol CH (2,6) 32.91 TAME CH2 19.26 iso-butyl acetate (CH3)2

126.99 p-cymene CH (3,5) 32.61 n-heptane CH2 (3,5) 18.87 ethanol CH3 126.78 m-xylene CH (4,6) 32.51 CPME CH2 (2,5) 16.66 ETBE CH3

126.58 o-xylene CH (4,5) 31.74 iso-butanol CH 16.08 ethylbenzene CH3 126.40 ethylbenzene CH (4) 31.61 tert-butanol CH3 14.50 ethyl acetate CH2CH3

126.11 toluene CH(4) 31.50 n-butyl acetate OCH2CH2 14.48 L-ethyl lactate CH3CH2 124.54 pyridine CH (3,5) 30.60 acetone CH3 14.33 n-heptane CH3

121.25 anisole CH (4) 30.15 MIBK CH3CO 14.20 n-butanol CH3 117.60 acetonitrile CN 29.74 n-heptane CH2 (4) 13.94 n-butyl acetate CH2CH3

114.68 anisole CH (2,6) 29.43 ethylbenzene CH2 8.40 TAME CH2CH3 83.35 CPME CH 29.30 methyl ethyl ketone CH3CO 8.03 methyl ethyl ketone CH2CH3

75.50 2-MeTHF CH 1.12 acetonitrile CH3

SI 7

Table S5. 1H NMR data by chemical shifts (ppm) in DMSO-d6


8.59-8.57 pyridine CH (2,6) m 2.25 cyclohexanone CH2 (2,6) t, 7

8.14 formic acid HCO s 2.25 p-cymene Ar-CH3 s 7.79 pyridine CH (4) tt, 7.6, 1.8 2.24 p-xylene CH3 s

7.45-7.32 chlorobenzene CH m 2.22 acetic anhydride CH3 s 7.40-7.37 pyridine CH (3,5) m 2.21 o-xylene CH3 s

7.36-7.28 benzyl alcohol CH m 2.09 acetone CH3 s 7.31-7.26 anisole CH (3,5) m 2.09-2.05 sulfolane CH2 m

7.29-7.26 ethyl benzene CH (3,5) m 2.07 acetonitrile CH3 s

7.27-7.23 toluene CH (3,5) m 2.07 methyl ethyl ketone CH3CO s

7.25-7.20 benzyl alcohol CH m 2.06 MIBK CH3CO s 7.22-7.14 ethyl benzene CH (2,6) m 2.02 glycol diacetate CH3 s

7.22-7.14 ethyl benzene CH (4) m 2.01 iso-butyl acetate CH3CO s 7.19-7.13 toluene CH (2,4,6) m 2.00 methyl acetate CH3CO s

7.14-7.04 o-xylene CH m 1.99 iso-amyl acetate CH3CO s

7.13 m-xylene CH (5) t, 7.5 1.99 n-butyl acetate CH3CO s

7.12-7.07 p-cymene ArH m 1.99 ethyl acetate CH3CO s 7.05 p-xylene CH s 1.99 MIBK CH nonet, 6.8

6.99-6.95 m-xylene CH (2,4,6) m 1.97-1.72 2-MeTHF Hc, HD, HE m 6.94-6.90 anisole CH (2,4,6) m 1.96 iso-propyl acetate CH3CO s

5.76 dichloromethane CH2 s 1.91 acetic acid CH3 s

5.35 L-ethyl lactate OH d, 5.5 1.90-1.84 DMPU CH2 m

5.16 benzyl alcohol OH t, 5.9 1.87 iso-butyl acetate CH nonet, 6.7 4.86 iso-propyl acetate CH sept, 6.3 1.78-1.75 tetrahydrofuran CH2 m

4.63 ethanol OH s 1.74-1.78 cyclohexanone CH2 (3,5) m 4.49 benzyl alcohol CH2 d, 5.9 1.67-1.42 CPME CH2 m

4.46-4.43 ethylene glycol OH m 1.67-1.57 methyl cyclohexane CH2 m

4.40 iso-butanol OH t, 5.5 1.65 iso-amyl alcohol CH nonet, 6.7

4.35 tert-butanol OH t, 5.2 1.64 iso-amyl acetate CH nonet, 6.7 4.34 iso-propanol OH d, 4.3 1.64-1.66 cyclohexanone CH2 (4) m

4.31 n-butanol OH t, 5.3 1.60 iso-butanol CH nonet, 6.6 4.29 iso-amyl alcohol OH t, 5.2 1.57-1.50 n-butyl acetate OCH2CH2 m

4.19 glycol diacetate CH2 s 1.45 iso-amyl acetate CH2CH q, 6.9

4.14-4.08 L-ethyl lactate CH m 1.43-1.25 n-butanol CH2CH2OH m

4.10 methanol OH q, 5.3 1.43-1.25 n-butanol CH2CH3 m 4.08 L-ethyl lactate CH2 q, 7.1 1.42 TAME CH2 q, 7.5

4.03 ethyl acetate CH2CH3 q, 7 1.40 cyclohexane CH2 s 4.02 iso-amyl acetate OCH2 t, 6.8 1.38-1.03 methyl cyclohexane CH2, CH m

3.99 n-butyl acetate OCH2 t, 6.7 1.37-1.27 n-butyl acetate CH2CH3 m

3.82 2-MeTHF CH dp, 7.9, 6.1 1.31 iso-amyl alcohol CH2CH q, 6.8

3.79 iso-butyl acetate CH2 d, 6.7 1.31 2-MeTHF HF ddt, 11.7, 8.8, 7.6 3.77 iso-propanol CH septd, 6.1, 4.3 1.30-1.22 n-heptane CH2 m

3.76-3.71 CPME CH m 1.24 L-ethyl lactate CH3CH d, 6.9 3.75 anisole OCH3 s 1.19 L-ethyl lactate CH3CH2 t, 7.1

3.75 2-MeTHF OCHAHB td, 7.7, 5.9 1.17 p-cymene (CH3)2 d, 6.9 3.69 dimethyl carbonate CH3 s 1.17 ethyl acetate CH2CH3 t, 7

3.62-3.59 tetrahydrofuran CH2O m 1.17 iso-propyl acetate (CH3)2 d, 6.3 3.57 methyl acetate OCH3 s 1.17 ethyl benzene CH3 t, 7.6

3.55 2-MeTHF OCHAHB td, 8.0, 6.3 1.12 ETBE (CH3)3 s 3.44 ethanol CH2 qd, 7.0, 5.2 1.12 2-MeTHF CH3 d, 6.1

3.41 iso-amyl alcohol CH2OH td, 6.8, 5.2 1.11 tert-butanol CH3 s 3.40-3.38 ethylene glycol CH2 m 1.11 MTBE CCH3 s

3.38 n-butanol CH2OH td, 6.5, 5.3 1.06 ethanol CH3 t, 7.0 3.33 ETBE CH2 q, 7.0 1.05 TAME (CH3)2 s

3.20-3.17 DMPU NCH2 m 1.04 ETBE CH3 t, 7.0 3.17 methanol CH3 d, 5.3 1.04 iso-propanol CH3 d, 6.1

3.15 iso-butanol CH2 dd, 6.5, 5.5 0.91-0.81 methyl cyclohexane CH2 m 3.15 CPME OCH3 s 0.91 methyl ethyl ketone CH2CH3 t, 7

3.08 MTBE OCH3 s 0.89 n-butyl acetate CH2CH3 t, 7.4 3.05 TAME OCH3 s 0.88 iso-amyl acetate (CH3)2 d, 6.6

3.01-2.97 sulfolane CH2SO2 m 0.88 iso-butyl acetate (CH3)2 d, 6.7 2.83 p-cymene CH(CH3)2 sept, 6.9 0.86 n-butanol CH3 t, 7.3

2.75 DMPU NCH3 s 0.86 n-heptane CH3 t, 6.8 2.60 ethyl benzene CH2 q, 7.6 0.85 iso-amyl alcohol CH3 d, 6.7

2.54 dimethyl sulfoxide CH3 s 0.85 MIBK (CH3)2 d, 6.7 2.43 methyl ethyl ketone CH2 q, 7 0.84 methyl cyclohexane CH3 d, 6.6

2.30 MIBK CH2 d, 7.0 0.82 iso-butanol CH3 d, 6.7 2.30 toluene CH3 s 0.79 TAME CH2CH3 t, 7.5

2.26 m-xylene CH3 s

SI 8

Table S6. 13

C NMR data by chemical shifts (ppm) in DMSO-d6


210.63 cyclohexanone CO 73.85 TAME C 27.39 ETBE (CH3)3

208.72 methyl ethyl ketone CO 72.04 MTBE C 27.16 iso-butyl acetate CH 208.02 MIBK CO 71.88 ETBE C 26.79 MTBE CCH3

206.31 acetone CO 69.61 iso-butyl acetate CH2 26.46 cyclohexanone CH2 (3,5) 174.49 L-ethyl lactate CO 67.83 iso-butanol CH2 26.33 cyclohexane CH2

171.93 acetic acid CO 67.07 tetrahydrofuran CH2O 25.91 methyl cyclohexane CH2 170.73 methyl acetate CO 66.89 iso-propyl acetate CH 25.86 methyl cyclohexane CH2

170.31 ethyl acetate CO 66.88 tert-butanol C 25.43 iso-propanol CH3 170.28 iso-amyl acetate CO 66.65 2-MeTHF CH2O 25.32 2-MeTHF CH2CH2O

170.28 iso-butyl acetate CO 65.91 L-ethyl lactate CH 25.19 tetrahydrofuran CH2 170.27 n-butyl acetate CO 64.92 iso-propanol CH 24.47 iso-amyl acetate CH

170.15 glycol diacetate CO 63.40 n-butyl acetate OCH2 24.32 cyclohexanone CH2 (4) 169.72 iso-propyl acetate CO 62.82 benzyl alcohol CH2 24.20 TAME (CH3)2

166.89 acetic anhydride CO 62.76 ethylene glycol CH2 24.18 iso-amyl alcohol CH 162.86 formic acid CO 62.18 iso-amyl acetate OCH2 23.89 p-cymene (CH3)2

159.30 anisole C (1) 61.85 glycol diacetate CH2 23.83 MIBK CH 155.89 DMPU CO 60.31 n-butanol CH2OH 23.05 CPME CH2 (3,4)

155.76 dimethyl carbonate CO 59.90 L-ethyl lactate CH2 22.71 methyl cyclohexane CH3 149.54 pyridine CH (2,6) 59.74 ethyl acetate CH2 22.52 iso-amyl alcohol CH3

145.22 p-cymene C (4) 58.91 iso-amyl alcohol CH2OH 22.23 MIBK (CH3)2 143.65 ethylbenzene C (1) 56.07 ethanol CH2 22.20 iso-amyl acetate (CH3)2

142.44 benzyl alcohol C (1) 56.03 ETBE CH2 22.07 sulfolane CH2 137.26 toluene C (1) 55.47 CPME CH3 22.00 n-heptane CH2 (2,6)

137.07 m-xylene C (1,3) 54.87 anisole CH3 21.90 acetic anhydride CH3 136.01 pyridine CH (4) 54.84 dichloromethane CH2 21.76 DMPU CH2

135.91 o-xylene C (1) 54.63 dimethyl carbonate CH3 21.53 iso-propyl acetate (CH3)2 134.46 p-cymene C (1) 51.74 MIBK CH2 21.00 iso-propyl acetate CH3CO

134.03 p-xylene C (1,4) 51.17 methyl acetate OCH3 20.95 acetic acid CH3 133.00 chlorobenzene C (1) 50.51 sulfolane CH2SO2 20.95 toluene CH3

130.20 chlorobenzene CH (3,5) 48.70 MTBE OCH3 20.83 m-xylene CH3 129.51 m-xylene CH (2) 48.59 methanol CH3 20.81 2-MeTHF CH3

129.40 anisole CH (3,5) 48.29 TAME OCH3 20.68 ethyl acetate CH3CO 129.29 o-xylene CH (3,6) 47.31 DMPU NCH2 20.64 iso-amyl acetate CH3CO

128.81 toluene CH (2,6) 41.54 iso-amyl alcohol CH2CH 20.60 n-butyl acetate CH3CO 128.72 p-cymene CH (2,6) 41.32 cyclohexanone CH2 (2,6) 20.57 iso-butyl acetate CH3CO

128.69 p-xylene CH (2,3,5,6) 40.45 dimethyl sulfoxide CH3 20.51 glycol diacetate CH3

128.30 chlorobenzene CH (2,6) 36.83 iso-amyl acetate CH2CH 20.49 p-xylene CH3

128.18 ethylbenzene CH (3,5) 35.83 methyl ethyl ketone CH2 20.48 p-cymene Ar-CH3 128.11 toluene CH (3,5) 35.11 DMPU CH3 20.40 methyl acetate CH3CO

127.98 m-xylene CH (5) 34.96 methyl cyclohexane CH2CH 20.30 L-ethyl lactate CH3CH 127.92 benzyl alcohol CH (3,5) 34.63 n-butanol CH2CH2OH 19.24 o-xylene CH3

127.63 ethylbenzene CH (2,6) 32.92 p-cymene CH(CH3)2 19.09 iso-butanol CH3

126.92 chlorobenzene CH (4) 32.62 2-MeTHF CH2CH 18.79 iso-butyl acetate (CH3)2

126.50 benzyl alcohol CH (4) 32.20 methyl cyclohexane CH 18.56 n-butanol CH2CH3 126.31 benzyl alcohol CH (2,6) 31.65 TAME CH2 18.54 n-butyl acetate CH2CH3

125.98 p-cymene CH (3,5) 31.35 CPME CH2 (2,5) 18.51 ethanol CH3 125.83 m-xylene CH (4,6) 31.17 n-heptane CH2 (3,5) 16.17 ETBE CH3

125.61 o-xylene CH (4,5) 30.56 acetone CH3 15.55 ethylbenzene CH3

125.50 ethylbenzene CH (4) 30.53 iso-butanol CH 14.40 ethyl acetate CH2CH3

125.22 toluene CH(4) 30.38 tert-butanol CH3 14.04 L-ethyl lactate CH3CH2 123.80 pyridine CH (3,5) 30.12 n-butyl acetate OCH2CH2 13.84 n-heptane CH3

120.41 anisole CH (4) 29.98 MIBK CH3CO 13.75 n-butanol CH3 117.91 acetonitrile CN 29.26 methyl ethyl ketone CH3CO 13.44 n-butyl acetate CH2CH3

113.87 anisole CH (2,6) 28.27 n-heptane CH2 (4) 8.00 TAME CH2CH3

81.92 CPME CH 28.11 ethylbenzene CH2 7.61 methyl ethyl ketone CH2CH3

74.21 2-MeTHF CH


SI 9

Table S7. 1H NMR data by chemical shifts (ppm) in CD3CN


8.58-8.56 pyridine CH (2,6) m 2.27 cyclohexanone CH2 (2,6) t, 7

8.03 formic acid HCO s 2.27 p-xylene CH3 s 7.73 pyridine CH (4) tt, 7.6, 1.8 2.25 o-xylene CH3 s

7.41-7.29 chlorobenzene CH m 2.18 acetic anhydride CH3 s 7.37-7.30 benzyl alcohol CH m 2.17 methanol OH q, 5.3

7.34-7.31 pyridine CH (3,5) m 2.16-2.12 sulfolane CH2 m 7.32-7.27 anisole CH (3,5) m 2.08 acetone CH3 s

7.30-7.25 ethyl benzene CH (3,5) m 2.08-2.02 MIBK CH m

7.29-7.23 benzyl alcohol CH m 2.06 methyl ethyl ketone CH3CO s

7.27-7.23 toluene CH (3,5) m 2.05 MIBK CH3CO s 7.23-7.21 ethyl benzene CH (2,6) m 2.01 glycol diacetate CH3 s

7.20-7.13 toluene CH (2,4,6) m 2.00-1.76 2-MeTHF Hc, HD, HE m 7.19-7.14 ethyl benzene CH (4) m 1.99 iso-butyl acetate CH3CO s

7.15-7.05 o-xylene CH m 1.99 methyl acetate CH3CO s

7.14-7.09 p-cymene ArH m 1.97 iso-amyl acetate CH3CO s

7.13 m-xylene CH (5) t, 7.5 1.97 n-butyl acetate CH3CO s 7.06 p-xylene CH s 1.97 ethyl acetate CH3CO s

7.01-6.96 m-xylene CH (2,4,6) m 1.96 acetic acid CH3 s 6.96-6.90 anisole CH (2,4,6) m 1.96 acetonitrile CH3 s

5.44 dichloromethane CH2 s 1.94-1.88 DMPU CH2 m

4.91 iso-propyl acetate CH sept, 6.3 1.94 iso-propyl acetate CH3CO s

4.57 benzyl alcohol CH2 d, 5.9 1.90 iso-butyl acetate CH nonet, 6.7 4.21-4.11 L-ethyl lactate CH m 1.82-1.79 tetrahydrofuran CH2 m

4.21-4.11 L-ethyl lactate CH2 m 1.79-1.84 cyclohexanone CH2 (3,5) m 4.21 glycol diacetate CH2 s 1.71-1.59 methyl cyclohexane CH2 m

4.06 ethyl acetate CH2CH3 q, 7 1.70-1.48 CPME CH2 m

4.05 iso-amyl acetate OCH2 t, 6.8 1.67 iso-amyl acetate CH nonet, 6.7

4.02 n-butyl acetate OCH2 t, 6.7 1.67 iso-amyl alcohol CH nonet, 6.7 3.86 iso-propanol CH septd, 6.1, 4.3 1.67-1.72 cyclohexanone CH2 (4) m

3.85 2-MeTHF CH dp, 7.9, 6.1 1.66 iso-butanol CH nonet, 6.6 3.81 iso-butyl acetate CH2 d, 6.7 1.61-1.54 n-butyl acetate OCH2CH2 m

3.79 2-MeTHF OCHAHB td, 7.7, 5.9 1.49 iso-amyl acetate CH2CH q, 6.9

3.78-3.74 CPME CH m 1.49-1.42 n -butanol CH2CH2OH m

3.77 anisole OCH3 s 1.46 TAME CH2 q, 7.5 3.72 dimethyl carbonate CH3 s 1.44 cyclohexane CH2 s

3.66-3.63 tetrahydrofuran CH2O m 1.41-1.32 n-butyl acetate CH2CH3 m 3.60 methyl acetate OCH3 s 1.40-1.08 methyl cyclohexane CH2, CH m

3.60 2-MeTHF OCHAHB td, 8.0, 6.3 1.39-1.29 n-butanol CH2CH3 m

3.54 ethanol CH2 qd, 7.0, 5.2 1.37 iso-amyl alcohol CH2CH q, 6.8

3.52-3.50 ethylene glycol CH2 m 1.35 2-MeTHF HF ddt, 11.7, 8.8, 7.6 3.51 iso-amyl alcohol CH2OH td, 6.8, 5.2 1.33-1.25 n-heptane CH2 m

3.48 n-butanol CH2OH td, 6.5, 5.3 1.31 L-ethyl lactate CH3CH d, 6.9 3.38 ETBE CH2 q, 7.0 1.23 L-ethyl lactate CH3CH2 t, 7.1

3.33 L-ethyl lactate OH d, 5.5 1.21 ethyl benzene CH3 t, 7.6 3.28 methanol CH3 d, 5.3 1.20 p-cymene (CH3)2 d, 6.9

3.25 iso-butanol CH2 dd, 6.5, 5.5 1.20 ethyl acetate CH2CH3 t, 7 3.22-3.19 DMPU NCH2 m 1.19 iso-propyl acetate (CH3)2 d, 6.3

3.19 CPME OCH3 s 1.17 tert-butanol CH3 s 3.14 benzyl alcohol OH t, 5.9 1.15 2-MeTHF CH3 d, 6.1

3.13 MTBE OCH3 s 1.14 ETBE (CH3)3 s 3.10 TAME OCH3 s 1.14 MTBE CCH3 s

2.96-2.92 sulfolane CH2SO2 m 1.11 ethanol CH3 t, 7.0 2.86 p-cymene CH(CH3)2 sept, 6.9 1.09 iso-propanol CH3 d, 6.1

2.81 DMPU NCH3 s 1.08 TAME (CH3)2 s 2.72-2.69 ethylene glycol OH m 1.07 ETBE CH3 t, 7.0

2.63 ethyl benzene CH2 q, 7.6 0.96 methyl ethyl ketone CH2CH3 t, 7 2.51 iso-propanol OH d, 4.3 0.94-0.84 methyl cyclohexane CH2 m

2.50 iso-butanol OH t, 5.5 0.92 n -butyl acetate CH2CH3 t, 7.4 2.50 dimethyl sulfoxide CH3 s 0.91 iso-amyl acetate (CH3)2 d, 6.6

2.47 ethanol OH t, 5.2 0.91 n-butanol CH3 t, 7.3 2.43 n-butanol OH t, 5.3 0.91 iso-butyl acetate (CH3)2 d, 6.7

2.43 methyl ethyl ketone CH2 q, 7 0.89 iso-amyl alcohol CH3 d, 6.7 2.40 iso-amyl alcohol OH t, 5.2 0.89 n-heptane CH3 t, 6.8

2.39 tert-butanol OH s 0.88 MIBK (CH3)2 d, 6.7 2.33 toluene CH3 s 0.86 iso-butanol CH3 d, 6.7

2.29 MIBK CH2 d, 7.0 0.86 methyl cyclohexane CH3 d, 6.6 2.28 p-cymene Ar-CH3 s 0.83 TAME CH2CH3 t, 7.5

2.28 m-xylene CH3 s

SI 10

Table S8. 13

C NMR data by chemical shifts (ppm) in CD3CN shift solvent carbon shift solvent carbon shift solvent carbon


209.88 methyl ethyl ketone CO 73.17 MTBE C 27.89 ETBE (CH3)3

209.34 MIBK CO 72.95 ETBE C 27.80 cyclohexanone CH2 (3,5) 207.43 acetone CO 71.02 iso-butyl acetate CH2 27.63 cyclohexane CH2

175.96 L-ethyl lactate CO 69.53 iso-butanol CH2 27.28 MTBE CCH3 173.21 acetic acid CO 68.74 tert-butanol C 27.21 methyl cyclohexane CH2

172.08 methyl acetate CO 68.32 tetrahydrofuran CH2O 27.09 methyl cyclohexane CH2

171.91 iso-amyl acetate CO 68.23 iso-propyl acetate CH 26.59 2-MeTHF CH2CH2O

171.73 n-butyl acetate CO 68.10 2-MeTHF CH2O 26.30 tetrahydrofuran CH2 171.71 iso-butyl acetate CO 67.57 L-ethyl lactate CH 25.90 iso-amyl acetate CH

171.68 ethyl acetate CO 64.84 n-butyl acetate OCH2 25.62 cyclohexanone CH2 (4) 171.52 glycol diacetate CO 64.79 benzyl alcohol CH2 25.56 iso-amyl alcohol CH

171.16 iso-propyl acetate CO 64.30 iso-propanol CH 25.55 iso-propanol CH3 168.02 acetic anhydride CO 64.22 ethylene glycol CH2 25.28 MIBK CH

162.57 formic acid CO 63.71 iso-amyl acetate OCH2 24.83 TAME (CH3)2 160.74 anisole C (1) 63.04 glycol diacetate CH2 24.41 p-cymene (CH3)2

157.54 DMPU CO 62.35 n-butanol CH2OH 24.28 CPME CH2 (3,4) 157.26 dimethyl carbonate CO 61.74 L-ethyl lactate CH2 23.45 n-heptane CH2 (2,6)

150.78 pyridine CH (2,6) 60.98 ethyl acetate CH2 23.38 sulfolane CH2 146.91 p-cymene C (4) 60.94 iso-amyl alcohol CH2OH 23.22 methyl cyclohexane CH3

145.42 ethylbenzene C (1) 57.96 ethanol CH2 23.10 DMPU CH2 143.17 benzyl alcohol C (1) 57.32 ETBE CH2 22.96 iso-amyl alcohol CH3

138.94 toluene C (1) 56.38 CPME CH3 22.75 MIBK (CH3)2 138.80 m-xylene C (1,3) 55.76 anisole CH3 22.74 iso-amyl acetate (CH3)2

137.51 o-xylene C (1) 55.39 dimethyl carbonate CH3 22.45 acetic anhydride CH3 136.91 pyridine CH (4) 55.32 dichloromethane CH2 22.06 iso-propyl acetate (CH3)2

136.16 p-cymene C (1) 53.04 MIBK CH2 21.55 iso-propyl acetate CH3CO 135.68 p-xylene C (1,4) 51.97 methyl acetate OCH3 21.50 toluene CH3

134.74 chlorobenzene C (1) 51.86 sulfolane CH2SO2 21.40 m-xylene CH3 131.10 chlorobenzene CH (3,5) 49.90 methanol CH3 21.34 2-MeTHF CH3

130.71 m-xylene CH (2) 49.52 MTBE OCH3 21.17 iso-amyl acetate CH3CO 130.48 anisole CH (3,5) 49.16 TAME OCH3 21.16 ethyl acetate CH3CO

130.46 o-xylene CH (3,6) 48.69 DMPU NCH2 21.12 n-butyl acetate CH3CO 129.95 toluene CH (2,6) 42.66 iso-amyl alcohol CH2CH 21.05 iso-butyl acetate CH3CO

129.91 p-cymene CH (2,6) 42.44 cyclohexanone CH2 (2,6) 21.00 p-cymene Ar-CH3

129.85 p-xylene CH

(2,3,5,6) 41.31 dimethyl sulfoxide CH3 21.00 p-xylene CH3

129.45 chlorobenzene CH (2,6) 38.16 iso-amyl acetate CH2CH 20.98 glycol diacetate CH3

129.34 ethylbenzene CH (3,5) 37.09 methyl ethyl ketone CH2 20.81 methyl acetate CH3CO 129.26 benzyl alcohol CH (3,5) 36.19 methyl cyclohexane CH2CH 20.77 L-ethyl lactate CH3CH

129.25 toluene CH (3,5) 35.81 DMPU CH3 20.73 acetic acid CH3 129.16 m-xylene CH (5) 35.80 n-butanol CH2CH2OH 19.87 n-butyl acetate CH2CH3

128.81 ethylbenzene CH (2,6) 34.48 p-cymene CH(CH3)2 19.80 n-butanol CH2CH3 127.97 benzyl alcohol CH (4) 33.85 2-MeTHF CH2CH 19.79 o-xylene CH3

127.83 chlorobenzene CH (4) 33.56 methyl cyclohexane CH 19.32 iso-butanol CH3 127.69 benzyl alcohol CH (2,6) 32.90 TAME CH2 19.29 iso-butyl acetate (CH3)2

127.23 p-cymene CH (3,5) 32.67 n-heptane CH2 (3,5) 18.80 ethanol CH3 126.95 m-xylene CH (4,6) 32.63 CPME CH2 (2,5) 16.72 ETBE CH3

126.78 o-xylene CH (4,5) 31.73 iso-butanol CH 16.17 ethylbenzene CH3 126.59 ethylbenzene CH (4) 31.52 n-butyl acetate OCH2CH2 14.54 ethyl acetate CH2CH3

126.29 toluene CH(4) 30.91 acetone CH3 14.52 L-ethyl lactate CH3CH2 124.77 pyridine CH (3,5) 30.68 tert-butanol CH3 14.41 n-heptane CH3

121.52 anisole CH (4) 30.43 MIBK CH3CO 14.24 n-butanol CH3

118.26 acetonitrile CN 29.80 n-heptane CH2 (4) 14.02 n-butyl acetate CH2CH3

114.85 anisole CH (2,6) 29.60 methyl ethyl ketone CH3CO 8.53 TAME CH2CH3 83.62 CPME CH 29.50 ethylbenzene CH2 7.14 methyl ethyl ketone CH2CH3

75.78 2-MeTHF CH


SI 11

Table S9. 1H NMR data by chemical shifts (ppm) in CD3OD


8.54-8.52 pyridine CH (2,6) m 2.21-2.18 sulfolane CH2 m

8.07 formic acid HCO s 2.15 acetone CH3 s 7.85 pyridine CH (4) tt, 7.6, 1.8 2.12 methyl ethyl ketone CH3CO s

7.45-7.42 pyridine CH (3,5) m 2.11 MIBK CH3CO s 7.37-7.25 chlorobenzene CH m 2.09 MIBK CH nonet, 6.8

7.36-7.30 benzyl alcohol CH m 2.06-1.85 2-MeTHF Hc, HD, HE m 7.28-7.22 anisole CH (3,5) m 2.04 glycol diacetate CH3 s

7.26-7.22 benzyl alcohol CH m 2.03 acetonitrile CH3 s

7.26-7.22 ethyl benzene CH (3,5) m 2.03 iso-butyl acetate CH3CO s

7.23-7.19 toluene CH (3,5) m 2.02 methyl acetate CH3CO s 7.18-7.16 ethyl benzene CH (2,6) m 2.01 iso-amyl acetate CH3CO s

7.16-7.09 toluene CH (2,4,6) m 2.01 n-butyl acetate CH3CO s 7.14-7.10 ethyl benzene CH (4) m 2.01 ethyl acetate CH3CO s

7.10-7.01 o-xylene CH m 2.00-1.94 DMPU CH2 m

7.09-7.04 p-cymene ArH m 1.99 acetic acid CH3 s

7.08 m-xylene CH (5) t, 7.5 1.99 iso-propyl acetate CH3CO s 7.02 p-xylene CH s 1.92 iso-butyl acetate CH nonet, 6.7

6.97-6.92 m-xylene CH (2,4,6) m 1.88-1.85 tetrahydrofuran CH2 m 6.92-6.87 anisole CH (2,4,6) m 1.85-1.87 cyclohexanone CH2 (3,5) m

5.49 dichloromethane CH2 s 1.77-1.50 CPME CH2 m

4.95 iso-propyl acetate CH sept, 6.3 1.74-1.76 cyclohexanone CH2 (4) m

4.59 benzyl alcohol CH2 s 1.72-1.61 methyl cyclohexane CH2 m 4.25 glycol diacetate CH2 s 1.71 iso-amyl alcohol CH nonet, 6.7

4.22 L-ethyl lactate CH q, 6.9 1.70 iso-butanol CH nonet, 6.6 4.18 L-ethyl lactate CH2 q, 7.1 1.69 iso-amyl acetate CH nonet, 6.7

4.09 iso-amyl acetate OCH2 t, 6.8 1.64-1.57 n-butyl acetate OCH2CH2 m

4.09 ethyl acetate CH2CH3 q, 7 1.55-1.47 n-butanol CH2CH2OH m

4.05 n-butyl acetate OCH2 t, 6.7 1.51 iso-amyl acetate CH2CH q, 6.9 3.95 2-MeTHF CH dp, 7.9, 6.1 1.51 TAME CH2 q, 7.5

3.92 iso-propanol CH sept, 6.1 1.45 cyclohexane CH2 s 3.86 2-MeTHF OCHAHB td, 7.7, 5.9 1.44-1.34 n-butyl acetate CH2CH3 m

3.85-3.80 CPME CH m 1.43-1.33 n-butanol CH2CH3 m

3.84 iso-butyl acetate CH2 d, 6.7 1.42 iso-amyl alcohol CH2CH q, 6.8

3.77 anisole OCH3 s 1.42 2-MeTHF HF dq, 11.6, 8.0 3.74 dimethyl carbonate CH3 s 1.40-1.09 methyl cyclohexane CH2, CH m

3.74-3.71 tetrahydrofuran CH2O m 1.36 L-ethyl lactate CH3CH d, 6.9 3.70 2-MeTHF OCHAHB td, 8.0, 6.3 1.34-1.24 n-heptane CH2 m

3.64 methyl acetate OCH3 s 1.27 L-ethyl lactate CH3CH2 t, 7.1

3.60 ethanol CH2 q, 7.1 1.24 ethyl acetate CH2CH3 t, 7

3.59 ethylene glycol CH2 s 1.22 tert-butanol CH3 s 3.57 iso-amyl alcohol CH2OH t, 6.9 1.22 iso-propyl acetate (CH3)2 d, 6.3

3.54 n-butanol CH2OH t, 6.5 1.21 p-cymene (CH3)2 d, 6.9 3.45 ETBE CH2 q, 7.0 1.21 ethyl benzene CH3 t, 7.6

3.34 methanol CH3 s 1.20 2-MeTHF CH3 d, 6.1 3.31-3.29 iso-butanol CH2 m 1.19 ETBE (CH3)3 s

3.30-3.27 DMPU NCH2 m 1.17 ethanol CH3 t, 7.0 3.26 CPME OCH3 s 1.15 iso-propanol CH3 d, 6.1

3.20 MTBE OCH3 s 1.15 MTBE CCH3 s 3.17 TAME OCH3 s 1.13 ETBE CH3 t, 7.0

3.03-2.99 sulfolane CH2SO2 m 1.13 TAME (CH3)2 s 2.88 DMPU NCH3 s 1.01 methyl ethyl ketone CH2CH3 t, 7

2.83 p-cymene CH(CH3)2 sept, 6.9 0.94 n-butyl acetate CH2CH3 t, 7.4 2.65 dimethyl sulfoxide CH3 s 0.94-0.84 methyl cyclohexane CH2 m

2.62 ethyl benzene CH2 q, 7.6 0.93 iso-amyl acetate (CH3)2 d, 6.6 2.50 methyl ethyl ketone CH2 q, 7 0.93 n-butanol CH3 t, 7.3

2.35 MIBK CH2 d, 7.0 0.93 iso-butyl acetate (CH3)2 d, 6.7 2.34 cyclohexanone CH2 (2,6) t, 7 0.91 iso-amyl alcohol CH3 d, 6.7

2.32 toluene CH3 s 0.91 MIBK (CH3)2 d, 6.7 2.27 p-cymene Ar-CH3 s 0.90 iso-butanol CH3 d, 6.7

2.27 m-xylene CH3 s 0.90 n-heptane CH3 t, 6.8 2.26 p-xylene CH3 s 0.87 methyl cyclohexane CH3 d, 6.6

2.24 o-xylene CH3 s 0.86 TAME CH2CH3 t, 7.5

SI 12

Table S10. 13

C NMR data by chemical shifts (ppm) in CD3OD



212.16 methyl ethyl ketone CO 74.32 MTBE C 28.16 cyclohexanone CH2 (3,5)

211.70 MIBK CO 74.13 ETBE C 27.96 cyclohexane CH2

209.67 acetone CO 71.73 iso-butyl acetate CH2 27.86 ETBE (CH3)3

176.41 L-ethyl lactate CO 69.95 iso-butanol CH2 27.52 methyl cyclohexane CH2

175.11 acetic acid CO 69.40 tert-butanol C 27.40 methyl cyclohexane CH2

173.21 methyl acetate CO 69.08 iso-propyl acetate CH 27.22 MTBE CCH3

173.08 iso-amyl acetate CO 68.82 tetrahydrofuran CH2O 26.77 2-MeTHF CH2CH2O

173.04 n-butyl acetate CO 68.68 2-MeTHF CH2O 26.50 tetrahydrofuran CH2

173.00 iso-butyl acetate CO 67.90 L-ethyl lactate CH 26.27 iso-amyl acetate CH

172.89 ethyl acetate CO 65.44 n-butyl acetate OCH2 25.86 iso-amyl alcohol CH

172.55 glycol diacetate CO 65.28 benzyl alcohol CH2 25.86 cyclohexanone CH2 (4)

172.52 iso-propyl acetate CO 64.71 iso-propanol CH 25.70 MIBK CH

164.41 formic acid CO 64.30 ethylene glycol CH2 25.27 iso-propanol CH3

161.15 anisole C (1) 64.22 iso-amyl acetate OCH2 24.83 TAME (CH3)2

158.90 DMPU CO 63.48 glycol diacetate CH2 24.55 p-cymene (CH3)2

157.91 dimethyl carbonate CO 62.71 n-butanol CH2OH 24.45 CPME CH2 (3,4)

150.12 pyridine CH (2,6) 61.98 L-ethyl lactate CH2 23.75 n-heptane CH2 (2,6)

146.99 p-cymene C (4) 61.50 ethyl acetate CH2 23.68 sulfolane CH2

145.48 ethylbenzene C (1) 61.28 iso-amyl alcohol CH2OH 23.30 methyl cyclohexane CH3

142.74 benzyl alcohol C (1) 58.26 ethanol CH2 23.04 DMPU CH2

138.93 toluene C (1) 57.95 ETBE CH2 23.02 iso-amyl alcohol CH3

138.79 m-xylene C (1,3) 56.55 CPME CH3 22.82 iso-amyl acetate (CH3)2

138.38 pyridine CH (4) 55.56 anisole CH3 22.82 MIBK (CH3)2

137.37 o-xylene C (1) 55.25 dimethyl carbonate CH3 22.03 iso-propyl acetate (CH3)2

136.15 p-cymene C (1) 54.78 dichloromethane CH2 21.51 toluene CH3

135.71 p-xylene C (1,4) 53.41 MIBK CH2 21.42 m-xylene CH3

135.31 chlorobenzene C (1) 52.04 methyl acetate OCH3 21.28 iso-propyl acetate CH3CO

131.00 chlorobenzene CH (3,5) 52.04 sulfolane CH2SO2 21.14 2-MeTHF CH3

130.70 m-xylene CH (2) 49.86 methanol CH3 21.03 p-cymene Ar-CH3

130.47 o-xylene CH (3,6) 49.66 MTBE OCH3 21.02 p-xylene CH3

130.41 anisole CH (3,5) 49.32 TAME OCH3 20.88 ethyl acetate CH3CO

129.94 toluene CH (2,6) 48.92 DMPU NCH2 20.87 iso-amyl acetate CH3CO

129.90 p-cymene CH (2,6) 42.70 iso-amyl alcohol CH2CH 20.83 n-butyl acetate CH3CO

129.84 p-xylene CH (2,3,5,6) 42.61 cyclohexanone CH2 (2,6) 20.76 iso-butyl acetate CH3CO

129.56 chlorobenzene CH (2,6) 40.45 dimethyl sulfoxide CH3 20.65 glycol diacetate CH3

129.37 benzyl alcohol CH (3,5) 38.53 iso-amyl acetate CH2CH 20.59 L-ethyl lactate CH3CH

129.33 ethylbenzene CH (3,5) 37.34 methyl ethyl ketone CH2 20.56 acetic acid CH3

129.23 toluene CH (3,5) 36.58 methyl cyclohexane CH2CH 20.50 methyl acetate CH3CO

129.13 m-xylene CH (5) 35.96 DMPU CH3 20.18 n-butyl acetate CH2CH3

128.80 ethylbenzene CH (2,6) 35.84 n-butanol CH2CH2OH 20.04 n-butanol CH2CH3

128.28 benzyl alcohol CH (4) 34.98 p-cymene CH(CH3)2 19.77 o-xylene CH3

128.01 benzyl alcohol CH (2,6) 34.05 2-MeTHF CH2CH 19.38 iso-butanol CH3

127.73 chlorobenzene CH (4) 33.99 methyl cyclohexane CH 19.36 iso-butyl acetate (CH3)2

127.19 p-cymene CH (3,5) 33.06 n-heptane CH2 (3,5) 18.40 ethanol CH3

126.99 m-xylene CH (4,6) 32.99 TAME CH2 16.47 ETBE CH3

126.81 o-xylene CH (4,5) 32.85 CPME CH2 (2,5) 16.25 ethylbenzene CH3

126.62 ethylbenzene CH (4) 31.93 iso-butanol CH 14.52 L-ethyl lactate CH3CH2

126.32 toluene CH(4) 31.84 n-butyl acetate OCH2CH2 14.49 ethyl acetate CH2CH3

125.56 pyridine CH (3,5) 30.91 tert-butanol CH3 14.44 n-heptane CH3

121.59 anisole CH (4) 30.67 acetone CH3 14.24 n-butanol CH3

118.06 acetonitrile CN 30.27 MIBK CH3CO 14.03 n-butyl acetate CH2CH3

114.91 anisole CH (2,6) 30.17 n-heptane CH2 (4) 8.47 TAME CH2CH3

84.47 CPME CH 29.89 ethylbenzene CH2 8.09 methyl ethyl ketone CH2CH3

76.75 2-MeTHF CH 29.39 methyl ethyl ketone CH3CO 0.85 acetonitrile CH3

SI 13

Table S11. 1H NMR data by chemical shifts (ppm) in D2O


8.54-8.52 pyridine CH (2,6) m 2.22 acetone CH3 s

8.26 formic acid HCO s 2.21 MIBK CH3CO s 7.91-7.86 pyridine CH (4) m 2.19 methyl ethyl ketone CH3CO s

7.48-7.45 pyridine CH (3,5) m 2.12 glycol diacetate CH3 s 7.47-7.37 benzyl alcohol CH m 2.11 iso-butyl acetate CH3CO s

7.47-7.37 benzyl alcohol CH m 2.11-1.86 2-MeTHF Hc, HD, HE m 7.46-7.33 chlorobenzene CH m 2.09 n-butyl acetate CH3CO s

7.40 anisole CH (3,5) t, 8.0 2.09 methyl acetate CH3CO s

7.36-7.33 toluene CH (3,5) m 2.08 acetic acid CH3 s

7.29-7.22 toluene CH (2,4,6) m 2.08 MIBK CH nonet, 6.8 7.24 m-xylene CH (5) t, 7.5 2.07 iso-amyl acetate CH3CO s

7.18 p-xylene CH s 2.07 ethyl acetate CH3CO s 7.14-7.07 m-xylene CH (2,4,6) m 2.07 iso-propyl acetate CH3CO s

7.09-7.03 anisole CH (2,4,6) m 2.06 acetonitrile CH3 s

4.98 iso-propyl acetate CH sept, 6.3 1.98-1.92 DMPU CH2 m

4.65 benzyl alcohol CH2 s 1.94 iso-butyl acetate CH nonet, 6.7 4.40 L-ethyl lactate CH q, 6.9 1.91-1.88 tetrahydrofuran CH2 m

4.34 glycol diacetate CH2 s 1.86-1.51 CPME CH2 m 4.23 L-ethyl lactate CH2 q, 7.1 1.85-1.90 cyclohexanone CH2 (3,5) m

4.14 iso-amyl acetate OCH2 t, 6.8 1.75 iso-butanol CH nonet, 6.6

4.14 ethyl acetate CH2CH3 q, 7 1.70-1.75 cyclohexanone CH2 (4) m

4.12 n-butyl acetate OCH2 t, 6.7 1.67 iso-amyl acetate CH nonet, 6.7 4.03 2-MeTHF CH dp, 7.9, 6.1 1.67 iso-amyl alcohol CH nonet, 6.7

4.02 iso-propanol CH sept, 6.2 1.67-1.60 n-butyl acetate OCH2CH2 m 3.99-3.94 CPME CH m 1.57-1.50 n-butanol CH2CH2OH m

3.91 iso-butyl acetate CH2 d, 6.7 1.55 TAME CH2 q, 7.5

3.88 2-MeTHF OCHAHB td, 7.7, 5.9 1.53 iso-amyl acetate CH2CH q, 6.9

3.85 anisole OCH3 s 1.47 2-MeTHF HF dq, 12.0, 8.2 3.78-3.74 tetrahydrofuran CH2O m 1.44 iso-amyl alcohol CH2CH q, 6.8

3.74 2-MeTHF OCHAHB td, 8.0, 6.3 1.42-1.33 n-butyl acetate CH2CH3 m 3.69 dimethyl carbonate CH3 s 1.41 L-ethyl lactate CH3CH d, 6.9

3.69 methyl acetate OCH3 s 1.40-1.30 n-butanol CH2CH3 m

3.67 ethylene glycol CH2 s 1.33-1.23 n-heptane CH2 m

3.66 ethanol CH2 q, 7.1 1.28 L-ethyl lactate CH3CH2 t, 7.1 3.64 iso-amyl alcohol CH2OH t, 6.8 1.26 methyl ethyl ketone CH2CH3 t, 7

3.61 n-butanol CH2OH t, 6.6 1.25 iso-propyl acetate (CH3)2 d, 6.3 3.54 ETBE CH2 q, 7.0 1.25 tert-butanol CH3 s

3.38 iso-butanol CH2 d, 6.6 1.24 ethyl acetate CH2CH3 t, 7

3.36 methanol CH3 s 1.23 ETBE (CH3)3 s

3.30 CPME OCH3 s 1.23 2-MeTHF CH3 d, 6.1 3.30-3.27 DMPU NCH2 m 1.21 MTBE CCH3 s

3.22 MTBE OCH3 s 1.19 ethanol CH3 t, 7.1 3.20 TAME OCH3 s 1.18 iso-propanol CH3 d, 6.2

3.19-3.15 sulfolane CH2SO2 m 1.17 TAME (CH3)2 s 3.18 methyl ethyl ketone CH2 q, 7 1.15 ETBE CH3 t, 7.0

2.86 DMPU NCH3 s 0.93 iso-butyl acetate (CH3)2 d, 6.7 2.71 dimethyl sulfoxide CH3 s 0.91 n-butanol CH3 t, 7.3

2.43 MIBK CH2 d, 7.0 0.91 n-butyl acetate CH2CH3 t, 7.4 2.40 cyclohexanone CH2 (2,6) t, 7 0.90 iso-amyl alcohol CH3 d, 6.7

2.35 toluene CH3 s 0.90 MIBK (CH3)2 d, 6.7 2.31 m-xylene CH3 s 0.89 iso-amyl acetate (CH3)2 d, 6.6

2.30 p-xylene CH3 s 0.89 iso-butanol CH3 d, 6.7 2.26-2.22 sulfolane CH2 m 0.87 n-heptane CH3 t, 6.8

0.85 TAME CH2CH3 t, 7.5

SI 14

Table S12. 13

C NMR data by chemical shifts (ppm) in D2O

shift solvent carbon shift solvent carbon

221.22 cyclohexanone CO 48.24 DMPU NCH2

218.43 methyl ethyl ketone CO 42.02 cyclohexanone CH2 (2,6) 218.1 MIBK CO 40.96 iso-amyl alcohol CH2CH

215.94 acetone CO 39.39 dimethyl sulfoxide CH3 177.21 acetic acid CO 37.27 methyl ethyl ketone CH2

177.14 L-ethyl lactate CO 35.91 DMPU CH3 175.64 methyl acetate CO 34.06 n-butanol CH2CH2OH

175.52 iso-butyl acetate CO 32.93 2-MeTHF CH2CH 175.46 n-butyl acetate CO 31.87 CPME CH2 (2,5)

175.26 ethyl acetate CO 31.69 TAME CH2 174.77 iso-propyl acetate CO 30.89 acetone CH3

174.71 glycol diacetate CO 30.46 n-butyl acetate OCH2CH2 166.31 formic acid CO 30.37 iso-butanol CH

163.96 dimethyl carbonate CO 30.29 tert-butanol CH3

158.99 DMPU CO 30.24 MIBK CH3CO

149.16 pyridine CH (2,6) 29.49 methyl ethyl ketone CH3CO 140.84 benzyl alcohol C (1) 27.7 iso-butyl acetate CH

138.21 pyridine CH (4) 27.5 cyclohexanone CH2 (3,5) 129.34 benzyl alcohol CH (3,5) 27.16 ETBE (CH3)3

128.43 benzyl alcohol CH (4) 26.6 MTBE CCH3

128.06 benzyl alcohol CH (2,6) 25.77 2-MeTHF CH2CH2O

125.04 pyridine CH (3,5) 25.63 tetrahydrofuran CH2 119.68 acetonitrile CN 25.13 MIBK CH

84.4 CPME CH 24.77 cyclohexanone CH2 (4) 77.73 TAME C 24.65 iso-amyl alcohol CH

76.81 2-MeTHF CH 24.38 iso-propanol CH3

75.62 MTBE C 24.24 TAME (CH3)2

75.28 ETBE C 23.61 CPME CH2 (3,4) 72.22 iso-butyl acetate CH2 22.84 sulfolane CH2

70.36 tert-butanol C 22.39 iso-amyl alcohol CH3 70.28 iso-propyl acetate CH 22.26 MIBK (CH3)2

69.27 iso-butanol CH2 21.8 DMPU CH2

68.45 tetrahydrofuran CH2O 21.53 iso-propyl acetate CH3CO

68.13 2-MeTHF CH2O 21.44 iso-propyl acetate (CH3)2 67.37 L-ethyl lactate CH 21.15 ethyl acetate CH3CO

66.12 n-butyl acetate OCH2 21.06 n-butyl acetate CH3CO 64.88 iso-propanol CH 21.03 acetic acid CH3

64.51 benzyl alcohol CH2 20.99 iso-butyl acetate CH3CO

63.42 glycol diacetate CH2 20.84 glycol diacetate CH3

63.17 ethylene glycol CH2 20.73 methyl acetate CH3CO 62.84 L-ethyl lactate CH2 20.34 2-MeTHF CH3

62.32 ethyl acetate CH2 19.8 L-ethyl lactate CH3CH 62.17 n-butanol CH2OH 19.07 n-butyl acetate CH2CH3

60.82 iso-amyl alcohol CH2OH 18.97 n -butanol CH2CH3

58.05 ethanol CH2 18.83 iso-butanol CH3

57.88 ETBE CH2 18.77 iso-butyl acetate (CH3)2 56.04 CPME CH3 17.47 ethanol CH3

55.81 dimethyl carbonate CH3 15.66 ETBE CH3 52.96 MIBK CH2 13.92 ethyl acetate CH2CH3

52.77 methyl acetate OCH3 13.91 L-ethyl lactate CH3CH2 51.58 sulfolane CH2SO2 13.66 n-butanol CH3

49.5 methanol CH3 13.51 n-butyl acetate CH2CH3 49.37 MTBE OCH3 8.14 TAME CH2CH3

48.92 TAME OCH3 7.87 methyl ethyl ketone CH2CH3


SI 16

1H NMR of anisole in D2O

NMR Chemical Shifts of Trace Impurities - Amazon S3

Documents

Transcript of NMR Chemical Shifts of Trace Impurities - Amazon S3