-
5
-
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0029945602
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-
For a counter-example to the resonance effect, see
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For a counter-example to the resonance effect, see: Laidig, K. E.; Cameron, L. M. J. Am. Chem. Soc. 1996, 118, 1737-1742.
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(1996)
J. Am. Chem. Soc
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Laidig, K.E.1
Cameron, L.M.2
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6
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0042197520
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Galabov, B.; Ilieva, S.; Hadjieva, B.; Dinchova, E. J. Phys. Chem. A 2003, 107, 5854-5861.
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J. Phys. Chem. A
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Galabov, B.1
Ilieva, S.2
Hadjieva, B.3
Dinchova, E.4
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7
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1842846635
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Miwa, J. H.; Pallivathucal, L.; Gowda, S.; Lee, K. E. Org. Lett. 2002, 4, 4655-4657.
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(2002)
Org. Lett
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Miwa, J.H.1
Pallivathucal, L.2
Gowda, S.3
Lee, K.E.4
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10
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45749156032
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Reiner, A.; Wildemann, D.; Fischer, G.; Kiefhaber, T. J. Am. Chem. Soc. 2008, 130, 8079-8084.
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J. Am. Chem. Soc
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Reiner, A.1
Wildemann, D.2
Fischer, G.3
Kiefhaber, T.4
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11
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0032546068
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Ohwada, T.; Achiwa, T.; Okamoto, I.; Shudo, K. Tetrahedron Lett. 1998, 39, 865-868.
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(1998)
Tetrahedron Lett
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Ohwada, T.1
Achiwa, T.2
Okamoto, I.3
Shudo, K.4
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12
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0344236075
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Otani, Y.; Nagae, O.; Naruse, Y.; Inagaki, S.; Ohno, M.; Yamaguchi, K.; Yamamoto, G.; Uchiyama, M.; Ohwada, T. J. Am. Chem. Soc. 2003, 125, 15191-15199.
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J. Am. Chem. Soc
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Otani, Y.1
Nagae, O.2
Naruse, Y.3
Inagaki, S.4
Ohno, M.5
Yamaguchi, K.6
Yamamoto, G.7
Uchiyama, M.8
Ohwada, T.9
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14
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56449098611
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This is due to high-density packing of 1f with a Z-value of 8 and an aromatic stacking distance of 3.4 Å
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This is due to high-density packing of 1f with a Z-value of 8 and an aromatic stacking distance of 3.4 Å.
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17
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0001217756
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Ammann, C.; Meier, P.; Merbach, A. E. J. Magn. Reson. 1982, 46, 319-321.
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(1982)
J. Magn. Reson
, vol.46
, pp. 319-321
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Ammann, C.1
Meier, P.2
Merbach, A.E.3
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18
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4243664295
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Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
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(1991)
Chem. Rev
, vol.91
, pp. 165-195
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Hansch, C.1
Leo, A.2
Taft, R.W.3
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19
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56449130405
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Regression coefficients (r) and regression slopes (ρ, of corresponding amides are as follows see ref 11, r, 0.98, ρ, 0.61 for 4 and r, 0.99 and ρ, 0.82 for 5
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+ = 0.82 for 5.
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20
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0041519401
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Olsen, R. A.; Liu, L.; Ghaderi, N.; Johns, A.; Hatcher, M. E.; Mueller, L. J. J. Am. Chem. Soc. 2003, 125, 10125-10132.
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J. Am. Chem. Soc
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Olsen, R.A.1
Liu, L.2
Ghaderi, N.3
Johns, A.4
Hatcher, M.E.5
Mueller, L.J.6
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21
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0035820034
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The fact that the negative entropic contribution is larger in more polar nitrobenzene than in o-dichlorobenzene can be partially explained in terms of enhanced solvation of thioamides, especially of the bicyclic thioamides, upon rotation. As for solvent effects on thioamide rotation, see: Wiberg, K. B.; Rush, D. J. J. Am. Chem. Soc. 2001, 123, 2038-2046.
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The fact that the negative entropic contribution is larger in more polar nitrobenzene than in o-dichlorobenzene can be partially explained in terms of enhanced solvation of thioamides, especially of the bicyclic thioamides, upon rotation. As for solvent effects on thioamide rotation, see: Wiberg, K. B.; Rush, D. J. J. Am. Chem. Soc. 2001, 123, 2038-2046.
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22
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84989614083
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This observation is consistent with a previous study of the corresponding amides, i.e, monocyclic and acyclic amides, a Pinto, B. M, Grindley, T. B, Szarek, W. A. Magn. Reson. Chem. 1986, 24, 323-331
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This observation is consistent with a previous study of the corresponding amides, i.e., monocyclic and acyclic amides, (a) Pinto, B. M.; Grindley, T. B.; Szarek, W. A. Magn. Reson. Chem. 1986, 24, 323-331.
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23
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0038341764
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(b) Suarez, C.; Nicholas, E. J.; Bowman, M. R. J. Phys. Chem. A 2003, 107, 3024-3029.
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(2003)
J. Phys. Chem. A
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, pp. 3024-3029
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Suarez, C.1
Nicholas, E.J.2
Bowman, M.R.3
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24
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33748960439
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ΔH is equal to the difference of potential energy E plus RT, zero-point energy, and the thermal corrections. Thus, it is well accepted that ΔH‡ is approximately equal to ΔE (which is obtained by calculation) along the reaction coordinate. See: Houk, K. N, Li, Y, Evanseck, J. D. Angew. Chem, Int. Ed. Engl. 1992, 31, 682-708
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‡ is approximately equal to ΔE (which is obtained by calculation) along the reaction coordinate. See: Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682-708.
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25
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56449104322
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The planarity (in terms of α value) of the calculated structures of the thioamides was also dependent on the electron-withdrawing nature of the aromatic substituents. In the case of the bicyclic thioamides 1: 1h (R, NO2) 160.7° > 1g (R, CN) 160.1° > 1f (R, COOMe) 159.8° > 1e (R, Cl) 158.8° > 1a (R, H) ≈ 1d (R, CH3) 158.1° > 1c (R, OMe) 157.2° > 1b (R, N(CH3)2) 156.0°. In the case of the monocyclic 2: 2h (R, NO2) 172.5° > 2g (R, CN) ≈ 2f (R, COOMe) 172.0° > 2e (R, Cl) 171.3° ≈ 2a (R, H) 171.5° ≈ 2d (R, CH 3) 171.2° > 2c (R, OMe) 170.3° > 2b (R, N(CH3)2) 169.5°. The dependency of 2 was smaller than that of 1, which was consistent with the trend found in the cr
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2) 169.5°. The dependency of 2 was smaller than that of 1, which was consistent with the trend found in the crystal structures. See Table S1 in Supporting Information.
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26
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56449084034
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We thank an anonymous reviewer for valuable comment about the contribution of resonance structure D
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We thank an anonymous reviewer for valuable comment about the contribution of resonance structure D.
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