Use of Empirical Correlations to Determine Solvent Effects in the Solvolysis of S-Methyl Chlorothioformate
Abstract
:1. Introduction
2. Results and Discussion
3. Conclusions
4. Experimental Section
Acknowledgments
References and Notes
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Solvent (%)a | 1 @ 25.0 °C; 105k, s−1b | NTc | YCld |
---|---|---|---|
100% MeOH | 2.00 ± 0.07e | 0.17 | −1.2 |
90% MeOH | 4.29 ± 0.15 | −0.01 | −0.20 |
80% MeOH | 6.75 ± 0.27f | −0.06 | 0.67 |
100% EtOH | 0.884 ± 0.021g | 0.37 | −2.50 |
90% EtOH | 1.45 ± 0.15 | 0.16 | −0.90 |
80% EtOH | 2.44 ± 0.12h | 0.00 | 0.00 |
90% Acetone | 0.107 ± 0.007 | −0.35 | −2.39 |
80% Acetone | 0.334 ± 0.013 | −0.37 | −0.80 |
60% Acetone | 4.30 ± 0.20 | −0.52 | 1.00 |
97% TFE (w/w) | 0.986 ± 0.030 | −3.30 | 2.83 |
90% TFE (w/w) | 1.92 ± 0.13 | −2.55 | 2.85 |
70% TFE (w/w) | 13.2 ± 1.5 | −1.98 | 2.96 |
60T-40E | 0.321 ± 0.015 | −0.94 | 0.63 |
50T-50E | 0.333 ± 0.017 | −0.64 | 0.60 |
40T-60E | 0.431 ± 0.013 | −0.34 | −0.48 |
20T-80E | 0.537 ± 0.016 | 0.08 | −1.42 |
100% H2O | 820i | −1.38 | 4.57 |
97%HFIP (w/w) | 3.21 ± 0.15 | −5.26 | 5.17 |
90%HFIP (w/w) | 3.48 ± 0.092j | −3.84 | 4.41 |
70%HFIP (w/w) | 13.9 ± 0.78 | −2.94 | 3.83 |
Substrate | na | lb | mb | cc | Rd | Fe |
---|---|---|---|---|---|---|
1 | 20f | 0.23 ± 0.06 | −0.29 ± 0.16 | 0.637 | 12 | |
0.64 ± 0.12 | 0.60 ± 0.08 | 0.10 ± 0.13 | 0.879 | 29 | ||
13g | 0.21 ± 0.13 | −0.29 ± 0.16 | 0.435 | 3 | ||
1.47 ± 0.21 | 0.49 ± 0.07 | 0.14 ± 0.09 | 0.927 | 30 | ||
12h | 0.17 ± 0.15 | −0.34 ± 0.18 | 0.341 | 1 | ||
1.48 ± 0.18 | 0.44 ± 0.06 | 0.08 ± 0.08 | 0.949 | 40 | ||
8i | 0.24 ± 0.26 | −0.30 ± 0.97 | 0.341 | 1 | ||
0.79 ± 0.06 | 0.85 ± 0.07 | −0.27 ± 0.18 | 0.987 | 95 |
Substrate | na | lb | mb | l/m | cc | Rd | Fe |
---|---|---|---|---|---|---|---|
EtOCOClf | 28 | 1.56 ± 0.09 | 0.55 ± 0.03 | 2.84 | 0.19 ± 0.24 | 0.967 | 179 |
7 | 0.69 ± 0.13 | 0.82 ± 0.16 | 0.84 | −2.40 ± 0.27 | 0.946 | 17 | |
MeOCOClg | 19 | 1.59 ± 0.09 | 0.58 ± 0.05 | 2.74 | 0.16 ± 0.07 | 0.977 | |
PhOCOClh | 49 | 1.66 ± 0.05 | 0.56 ± 0.03 | 2.96 | 0.15 ± 0.07 | 0.980 | 568 |
PhSCSCli | 31 | 0.69 ± 0.05 | 0.95 ± 0.03 | 0.73 | 0.18 ± 0.05 | 0.987 | 521 |
PhOCSClj | 9 | 1.88 ± 0.28 | 0.56 ± 0.15 | 3.36 | 0.38 ± 0.15 | 0.950 | 28 |
18 | 0.34 ± 0.05 | 0.93 ± 0.09 | 0.37 | −2.54 ± 0.34 | 0.955 | 77 | |
PhSCOClk | 16 | 1.74 ± 0.17 | 0.48 ± 0.07 | 3.63 | 0.19 ± 0.23 | 0.946 | 55 |
6 | 0.62 ± 0.08 | 0.92 ± 0.11 | 0.67 | −2.29 ± 0.13 | 0.983 | 44 | |
EtSCOCll | 19 | 0.66 ± 0.08 | 0.93 ± 0.07 | 0.71 | −0.16 ± 0.31 | 0.961 | 96 |
MeOCOFm | 14 | 1.33 ± 0.09 | 0.73 ± 0.06 | 1.82 | −0.08 ± 0.08 | 0.972 |
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D’Souza, M.J.; Hailey, S.M.; Kevill, D.N. Use of Empirical Correlations to Determine Solvent Effects in the Solvolysis of S-Methyl Chlorothioformate. Int. J. Mol. Sci. 2010, 11, 2253-2266. https://doi.org/10.3390/ijms11052253
D’Souza MJ, Hailey SM, Kevill DN. Use of Empirical Correlations to Determine Solvent Effects in the Solvolysis of S-Methyl Chlorothioformate. International Journal of Molecular Sciences. 2010; 11(5):2253-2266. https://doi.org/10.3390/ijms11052253
Chicago/Turabian StyleD’Souza, Malcolm J., Stefan M. Hailey, and Dennis N. Kevill. 2010. "Use of Empirical Correlations to Determine Solvent Effects in the Solvolysis of S-Methyl Chlorothioformate" International Journal of Molecular Sciences 11, no. 5: 2253-2266. https://doi.org/10.3390/ijms11052253