Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (10): 3892-3902.DOI: 10.6023/cjoc202106018 Previous Articles Next Articles
Special Issue: 南开大学化学学科创立100周年; 热点论文虚拟合集
REVIEWS
黄谋新a, 贾宗宾b,c, 罗三中a,b,c,*(), 程津培a,d,*()
收稿日期:
2021-06-08
修回日期:
2021-06-27
发布日期:
2021-07-12
通讯作者:
罗三中, 程津培
作者简介:
基金资助:
Mouxin Huanga, Zongbin Jiab,c, Sanzhong Luoa,b,c(), Jin-Pei Chenga,d()
Received:
2021-06-08
Revised:
2021-06-27
Published:
2021-07-12
Contact:
Sanzhong Luo, Jin-Pei Cheng
About author:
Supported by:
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Mouxin Huang, Zongbin Jia, Sanzhong Luo, Jin-Pei Cheng. Quantitative Thermodynamic and Kinetic Parameters of Radical[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3892-3902.
Substituent | ArCH3 | ArCH2CN | ArCH(CN)CO2Et | |||||
---|---|---|---|---|---|---|---|---|
BDE | RSEa | BDE | RSE | BDE | RSE | |||
4-OMe | 362.2 | 6.0 | 337.1 | 6.3 | 327.9 | 8.4 | ||
4-Me | 366.6 | 1.6 | 340.9 | 2.5 | 334.8 | 1.5 | ||
H | 368.2 | (0) | 343.4 | (0) | 336.3 | (0) | ||
4-CO2Me | — | — | 346.6 | –3.2 | 343.2 | –6.9 | ||
4-CN | 388.0 | 0.2 | 345.4 | –2.0 | 348.1 | –11.8 | ||
Substituent (E+) | Ph-CH2-E+ | Ph-COCH2-E+ | 9-E+-fluorene | |||||
BDE | RSE | BDE | RSE | BDE | RSE | |||
H | 370.5 | (0) | 388.9 | (0) | 332.5 | (0) | ||
Ph3P+ | 370.9 | –0.4 | 403.6 | –14.6 | 341.3 | –8.8 | ||
(n-Bu)3P+ | 373.0 | –2.5 | 406.5 | –17.6 | 347.1 | –14.6 | ||
Me3N+ | 379.7 | –9.2 | 404.8 | –15.9 | 355.1 | –22.6 | ||
Ph3As+ | 383.5 | –13.0 | 400.2 | –11.3 | 345.4 | –13.0 | ||
Substituent | ArNH2 | ArNHCOMe | ArC(Me)=NNHCONH2 | |||||
BDE | RSE | BDE | RSE | BDE | RSE | |||
4-OMe | 378.2 | 8.0 | 400.1 | 15.4 | 381.0 | 3.2 | ||
4-Me | 384.9 | 1.3 | 408.0 | 7.5 | 382.6 | 1.6 | ||
H | 386.2 | (0) | 415.5 | (0) | 384.2 | (0) | ||
4-CN | 398.3 | –12.1 | 424.8 | –9.3 | 388.2 | –4.0 | ||
4-NO2 | 404.6 | –18.4 | 427.5 | –12.0 | 387.2 | –3.0 | ||
Substituent | ArNHPh | ArNHNH2 | ArNHOH | |||||
BDE | RSE | BDE | RSE | BDE | RSE | |||
4-Me | 365 | 2 | 302 | 3 | 284 | 8 | ||
H | 367 | (0) | 305 | (0) | 292 | (0) | ||
4-CN | — | — | 326 | –21 | — | — | ||
Substituent | ArNHPO(OEt)2 | ArNH(P+Ph3) | ||||||
BDE | RSE | BDE | RSE | |||||
4-Me | 391 | 6 | 288 | –2 | ||||
H | 397 | (0) | 286 | (0) | ||||
4-CN | 414 | –17 | 271 | 15 |
Substituent | ArCH3 | ArCH2CN | ArCH(CN)CO2Et | |||||
---|---|---|---|---|---|---|---|---|
BDE | RSEa | BDE | RSE | BDE | RSE | |||
4-OMe | 362.2 | 6.0 | 337.1 | 6.3 | 327.9 | 8.4 | ||
4-Me | 366.6 | 1.6 | 340.9 | 2.5 | 334.8 | 1.5 | ||
H | 368.2 | (0) | 343.4 | (0) | 336.3 | (0) | ||
4-CO2Me | — | — | 346.6 | –3.2 | 343.2 | –6.9 | ||
4-CN | 388.0 | 0.2 | 345.4 | –2.0 | 348.1 | –11.8 | ||
Substituent (E+) | Ph-CH2-E+ | Ph-COCH2-E+ | 9-E+-fluorene | |||||
BDE | RSE | BDE | RSE | BDE | RSE | |||
H | 370.5 | (0) | 388.9 | (0) | 332.5 | (0) | ||
Ph3P+ | 370.9 | –0.4 | 403.6 | –14.6 | 341.3 | –8.8 | ||
(n-Bu)3P+ | 373.0 | –2.5 | 406.5 | –17.6 | 347.1 | –14.6 | ||
Me3N+ | 379.7 | –9.2 | 404.8 | –15.9 | 355.1 | –22.6 | ||
Ph3As+ | 383.5 | –13.0 | 400.2 | –11.3 | 345.4 | –13.0 | ||
Substituent | ArNH2 | ArNHCOMe | ArC(Me)=NNHCONH2 | |||||
BDE | RSE | BDE | RSE | BDE | RSE | |||
4-OMe | 378.2 | 8.0 | 400.1 | 15.4 | 381.0 | 3.2 | ||
4-Me | 384.9 | 1.3 | 408.0 | 7.5 | 382.6 | 1.6 | ||
H | 386.2 | (0) | 415.5 | (0) | 384.2 | (0) | ||
4-CN | 398.3 | –12.1 | 424.8 | –9.3 | 388.2 | –4.0 | ||
4-NO2 | 404.6 | –18.4 | 427.5 | –12.0 | 387.2 | –3.0 | ||
Substituent | ArNHPh | ArNHNH2 | ArNHOH | |||||
BDE | RSE | BDE | RSE | BDE | RSE | |||
4-Me | 365 | 2 | 302 | 3 | 284 | 8 | ||
H | 367 | (0) | 305 | (0) | 292 | (0) | ||
4-CN | — | — | 326 | –21 | — | — | ||
Substituent | ArNHPO(OEt)2 | ArNH(P+Ph3) | ||||||
BDE | RSE | BDE | RSE | |||||
4-Me | 391 | 6 | 288 | –2 | ||||
H | 397 | (0) | 286 | (0) | ||||
4-CN | 414 | –17 | 271 | 15 |
Substituent | τp | ER | ED | ERN | σF• | σC• | σJ• | σα• |
---|---|---|---|---|---|---|---|---|
H | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
p-NO2 | 0.90 | 0.41 | 0.27 | 0.41 | 0.27 | 0.76 | ||
p-N=NPh | 0.90 | 0.33 | ||||||
p-NMe2 | 0.24 | –0.11 | ||||||
p-Ph | 0.42 | |||||||
p-COMe | 0.24 | 0.24 | 0.12 | 0.066 | ||||
p-COPh | 0.064 | |||||||
p-CN | 0.24 | 0.32 | 0.23 | 0.53 | 0.46 | 0.043 | ||
p-SMe | 0.34 | 0.43 | ||||||
p-CO2Me | 0.35 | 0.048 | ||||||
p-SOMe | 0.006 | |||||||
p-SO3Me | 0.003 | |||||||
p-OCOMe | 0.001 | |||||||
p-OMe | 0.14 | 0.11 | 0.19 | –0.008 | –0.12 | 0.24 | 0.42 | 0.034 |
p-SiMe3 | 0.17 | |||||||
p-Br | 0.12 | 0.072 | 0.17 | 0.14 | ||||
p-tBu | 0.03 | 0.014 | 0.13 | 0.036 | ||||
p-iPr | 0.03 | 0.034 | ||||||
p-F | –0.011 | |||||||
p-Cl | 0.16 | 0.10 | 0.07 | 0.062 | 0.08 | 0.12 | 0.18 | 0.017 |
p-I | 0.12 | 0.037 | 0.16 | |||||
p-OPh | 0.13 | –0.147 | ||||||
p-Me | 0.09 | 0.03 | 0.11 | –0.020 | –0.02 | 0.11 | 0.39 | 0.015 |
p-CF3 | 0.08 | 0.001 | ||||||
m-SiMe3 | 0.03 | |||||||
m-Me | –0.02 | –0.001 | ||||||
m-CO2Me | –0.004 | |||||||
m-OMe | –0.02 | |||||||
m-Cl | –0.04 | –0.001 | ||||||
m-F | –0.05 | |||||||
m-CF3 | –0.07 | –0.014 | ||||||
m-F | –0.08 | –0.018 | ||||||
m-CN | –0.12 | –0.039 | ||||||
m-OPh | –0.013 |
Substituent | τp | ER | ED | ERN | σF• | σC• | σJ• | σα• |
---|---|---|---|---|---|---|---|---|
H | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
p-NO2 | 0.90 | 0.41 | 0.27 | 0.41 | 0.27 | 0.76 | ||
p-N=NPh | 0.90 | 0.33 | ||||||
p-NMe2 | 0.24 | –0.11 | ||||||
p-Ph | 0.42 | |||||||
p-COMe | 0.24 | 0.24 | 0.12 | 0.066 | ||||
p-COPh | 0.064 | |||||||
p-CN | 0.24 | 0.32 | 0.23 | 0.53 | 0.46 | 0.043 | ||
p-SMe | 0.34 | 0.43 | ||||||
p-CO2Me | 0.35 | 0.048 | ||||||
p-SOMe | 0.006 | |||||||
p-SO3Me | 0.003 | |||||||
p-OCOMe | 0.001 | |||||||
p-OMe | 0.14 | 0.11 | 0.19 | –0.008 | –0.12 | 0.24 | 0.42 | 0.034 |
p-SiMe3 | 0.17 | |||||||
p-Br | 0.12 | 0.072 | 0.17 | 0.14 | ||||
p-tBu | 0.03 | 0.014 | 0.13 | 0.036 | ||||
p-iPr | 0.03 | 0.034 | ||||||
p-F | –0.011 | |||||||
p-Cl | 0.16 | 0.10 | 0.07 | 0.062 | 0.08 | 0.12 | 0.18 | 0.017 |
p-I | 0.12 | 0.037 | 0.16 | |||||
p-OPh | 0.13 | –0.147 | ||||||
p-Me | 0.09 | 0.03 | 0.11 | –0.020 | –0.02 | 0.11 | 0.39 | 0.015 |
p-CF3 | 0.08 | 0.001 | ||||||
m-SiMe3 | 0.03 | |||||||
m-Me | –0.02 | –0.001 | ||||||
m-CO2Me | –0.004 | |||||||
m-OMe | –0.02 | |||||||
m-Cl | –0.04 | –0.001 | ||||||
m-F | –0.05 | |||||||
m-CF3 | –0.07 | –0.014 | ||||||
m-F | –0.08 | –0.018 | ||||||
m-CN | –0.12 | –0.039 | ||||||
m-OPh | –0.013 |
Substituent | σmb | σJJ• | Substituent | σmb | σJJ• |
---|---|---|---|---|---|
H | 0 | 0 | p-OMe | –0.77 | 0.23 |
p-NMe2 | –0.96 | 1.00 | p-Br | 0.13 | 0.23 |
p-CF=CF2 | 0.40 | 0.86 | p-Cl | 0.11 | 0.22 |
p-SMe | –0.18 | 0.62 | p-CH=CH2 | 0.03 | |
p-COMe | 0.56 | 0.54 | p-Me | –0.29 | 0.15 |
p-SOMe | 0.19 | 0.50 | p-Et | 0.15 | |
p-Ph | 0.06 | 0.47 | p-CF3 | 0.49 | –0.01 |
p-CN | 0.86 | 0.42 | p-F | –0.24 | –0.02 |
p-COOH | 0.31 | 0.38 | m-Me | –0.20 | 0 |
p-CONH2 | 0.10 | 0.38 | m-Br | 0.36 | 0.12 |
p-SO2Me | 0.64 | 0.41 | m-tBu | –0.20 | 0.11 |
p-NO2 | 0.86 | 0.36 | m-CN | 0.89 | 0.11 |
p-OCOMe | -0.14 | 0.35 | m-OMe | –0.11 | 0.10 |
p-CO2Me | 0.48 | 0.33 | m-CO2Me | 0.21 | 0.10 |
p-SO2Me | 0.64 | 0.41 | m-Et | –0.15 | |
p-SiMe3 | 0.14 | 0.31 | m-F | 0.23 | 0.03 |
p-cPr | –0.31 | 0.29 | m-NO2 | 0.69 | 0.001 |
p-tBu | –0.22 | 0.26 | m-Cl | 0.12 | –0.05 |
p-OPh | –0.46 | m-CF3 | 0.39 | –0.07 |
Substituent | σmb | σJJ• | Substituent | σmb | σJJ• |
---|---|---|---|---|---|
H | 0 | 0 | p-OMe | –0.77 | 0.23 |
p-NMe2 | –0.96 | 1.00 | p-Br | 0.13 | 0.23 |
p-CF=CF2 | 0.40 | 0.86 | p-Cl | 0.11 | 0.22 |
p-SMe | –0.18 | 0.62 | p-CH=CH2 | 0.03 | |
p-COMe | 0.56 | 0.54 | p-Me | –0.29 | 0.15 |
p-SOMe | 0.19 | 0.50 | p-Et | 0.15 | |
p-Ph | 0.06 | 0.47 | p-CF3 | 0.49 | –0.01 |
p-CN | 0.86 | 0.42 | p-F | –0.24 | –0.02 |
p-COOH | 0.31 | 0.38 | m-Me | –0.20 | 0 |
p-CONH2 | 0.10 | 0.38 | m-Br | 0.36 | 0.12 |
p-SO2Me | 0.64 | 0.41 | m-tBu | –0.20 | 0.11 |
p-NO2 | 0.86 | 0.36 | m-CN | 0.89 | 0.11 |
p-OCOMe | -0.14 | 0.35 | m-OMe | –0.11 | 0.10 |
p-CO2Me | 0.48 | 0.33 | m-CO2Me | 0.21 | 0.10 |
p-SO2Me | 0.64 | 0.41 | m-Et | –0.15 | |
p-SiMe3 | 0.14 | 0.31 | m-F | 0.23 | 0.03 |
p-cPr | –0.31 | 0.29 | m-NO2 | 0.69 | 0.001 |
p-tBu | –0.22 | 0.26 | m-Cl | 0.12 | –0.05 |
p-OPh | –0.46 | m-CF3 | 0.39 | –0.07 |
Substituent | log K | M(H2O) |
---|---|---|
·H | 4.70 | 1.47 |
·OH | 4.33 | 1.10 |
·CH3 | 3.23 | 0.00 |
·CF3 | 4.18 | 0.95 |
·CCl3 | 4.23 | 1.00 |
·CH2OH | 2.48 | –0.75 |
·CH2CH2OH | 2.00 | –1.23 |
·C(CH3)2OH | 2.00 | –1.23 |
·CH2C(OH)(CH3)2 | 3.60 | 0.37 |
Substituent | log K | M(H2O) |
---|---|---|
·H | 4.70 | 1.47 |
·OH | 4.33 | 1.10 |
·CH3 | 3.23 | 0.00 |
·CF3 | 4.18 | 0.95 |
·CCl3 | 4.23 | 1.00 |
·CH2OH | 2.48 | –0.75 |
·CH2CH2OH | 2.00 | –1.23 |
·C(CH3)2OH | 2.00 | –1.23 |
·CH2C(OH)(CH3)2 | 3.60 | 0.37 |
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