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By configuration we mean cis - trans isomerism around double bonds as suggested by convention. We are distinguishing here between configurational and conformational rotation for the simple fact that energy barriers associated with these two processes are quite different. These differences in isomerization rates can be very important in future applications.
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By configuration we mean cis - trans isomerism around double bonds as suggested by convention. We are distinguishing here between configurational and conformational rotation for the simple fact that energy barriers associated with these two processes are quite different. These differences in isomerization rates can be very important in future applications.
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For some examples of conflicting reports on hydrazone isomerization mechanism, please see ref 25a and
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79959500826
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imin=N atoms it is -3.16(10)° for 1- E and -8.23(10)° for 2- E
-
imin=N atoms it is -3.16(10)° for 1- E and -8.23(10)° for 2- E
-
-
-
-
133
-
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0006213897
-
-
These types of hydrazones usually adopt planar structures. For other examples, please see
-
These types of hydrazones usually adopt planar structures. For other examples, please see: Vickery, B.; Willey, G. R.; Drew, M. G. B. J. Chem. Soc., Perkin Trans. 2 1981, 155-160
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Drew, M. G. B.; Vickery, B.; Willey, G. R. Acta Crystallogr., Sect. B 1982, 38, 1530-1535
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Drew, M.G.B.1
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136
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79959498760
-
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The bond length between the aromatic carbon and the hydrazone nitrogen (N2) is 1.401(1) Å for 1- E and 1.400(1) Å for 2- E, and the N(1)-N(2) bond length is 1.321(1) Å for 1- E and 1.326(1) Å for 2- E. The length of the imino double bond (C=N) is 1.305(1) Å for 1- E and 1.313(1) Å for 2- E.
-
The bond length between the aromatic carbon and the hydrazone nitrogen (N2) is 1.401(1) Å for 1- E and 1.400(1) Å for 2- E, and the N(1)-N(2) bond length is 1.321(1) Å for 1- E and 1.326(1) Å for 2- E. The length of the imino double bond (C=N) is 1.305(1) Å for 1- E and 1.313(1) Å for 2- E.
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137
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37049107390
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Kaberia, F.; Vickery, B.; Willey, G. R.; Drew, M. G. B. J. Chem. Soc., Perkin Trans. 2 1980, 1622-1626
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Kaberia, F.1
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0006213897
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Vickery, B.; Willey, G. R.; Drew, M. G. B. J. Chem. Soc., Perkin Trans. 2 1981, 155-160
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Vickery, B.1
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37049106359
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Vickery, B.; Willey, G. R.; Drew, M. G. B. J. Chem. Soc., Perkin Trans. 2 1981, 1454-1458
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Vickery, B.1
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Drew, M. G. B.; Vickery, B.; Willey, G. R. J. Chem. Soc., Perkin Trans. 2 1982, 1297-1303
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Drew, M.G.B.1
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67650744195
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146
-
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79959497598
-
-
The reason for this is most probably the unfavorable peri interaction in the other conformation (rotamer).
-
The reason for this is most probably the unfavorable peri interaction in the other conformation (rotamer).
-
-
-
-
147
-
-
79959521052
-
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release 110; Schrodinger: New York.
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Jaguar 7.6 User Manual, release 110; Schrodinger: New York, 2009.
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Jaguar 7.6 User Manual
-
-
-
152
-
-
79959514498
-
-
The error in the calculated absolute nuclear magnetic shifts was ∼1 ppm. However, the error in the relative nuclear magnetic shifts was observed to be ∼0.1 ppm.
-
The error in the calculated absolute nuclear magnetic shifts was ∼1 ppm. However, the error in the relative nuclear magnetic shifts was observed to be ∼0.1 ppm.
-
-
-
-
153
-
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0034703305
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a = 12.33)
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a = 12.33): Kaljurand, I.; Rodima, T.; Leito, I.; Koppel, I. A.; Schwesinger, R. J. Org. Chem. 2000, 65, 6202-6208
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Leito, I.3
Koppel, I.A.4
Schwesinger, R.5
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155
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79959525829
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In ethyl-2-pyridylacetate this same proton resonates at 8.50 ppm and shifts to 8.70 ppm upon protonation with TFA. This indicates that the shift to 8.76 ppm in 1- E has to do with the H-bonding and RAHB. In 1- Z the pyridine is not H-bonded, and proton H1 resonates at 8.55 ppm, clearly showing the effect of the H-bond on this proton.
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In ethyl-2-pyridylacetate this same proton resonates at 8.50 ppm and shifts to 8.70 ppm upon protonation with TFA. This indicates that the shift to 8.76 ppm in 1- E has to do with the H-bonding and RAHB. In 1- Z the pyridine is not H-bonded, and proton H1 resonates at 8.55 ppm, clearly showing the effect of the H-bond on this proton.
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156
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79959526763
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-
3 is used as the base, the fully equilibrated spectrum is generated instantaneously, and this process is not observed.
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3 is used as the base, the fully equilibrated spectrum is generated instantaneously, and this process is not observed.
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-
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157
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-
79959504890
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-
+.
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+.
-
-
-
-
158
-
-
79959525393
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-
Regardless of the isomerization or the protonation states of the hydrazone-based switches 1 and 2, the main absorption of 2 is constantly 10-20% less intense than that of 1.
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Regardless of the isomerization or the protonation states of the hydrazone-based switches 1 and 2, the main absorption of 2 is constantly 10-20% less intense than that of 1.
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159
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79959509456
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It is noteworthy that, at the beginning of the spectrophotometric titrations of 1- E and 2- E by TFA (Figures S15 and S16 in the SI), unexpected spectral variations were observed. These changes were attributed to the initial protonation of the Z isomer, which has more basic pyridyl nitrogen, as it is not involved in H-bonding as is the case in the E isomer. This observation supports the presence of a mixture of Z and E isomers in solution, in agreement with the NMR data. The E isomers remain by far the predominant species in solution (estimated >95%).
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It is noteworthy that, at the beginning of the spectrophotometric titrations of 1- E and 2- E by TFA (Figures S15 and S16 in the SI), unexpected spectral variations were observed. These changes were attributed to the initial protonation of the Z isomer, which has more basic pyridyl nitrogen, as it is not involved in H-bonding as is the case in the E isomer. This observation supports the presence of a mixture of Z and E isomers in solution, in agreement with the NMR data. The E isomers remain by far the predominant species in solution (estimated >95%).
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-
-
-
162
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79959491713
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-
Z→E values were used for the different calculations.
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Z→E values were used for the different calculations.
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-
-
-
163
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-
79959497176
-
-
3CN (see ref 28a) was overestimated because base catalysis was not taken into account.
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3CN (see ref 28a) was overestimated because base catalysis was not taken into account.
-
-
-
-
164
-
-
84982343024
-
-
T is an empirical measure of solvent polarity, which is based on the solvatochromism of a pyridinium phenoxide. This parameter mainly reflects the electrophilicity and the H-bond donor activity of the solvent and is generally used when intramolecular bonded systems are studied.
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T is an empirical measure of solvent polarity, which is based on the solvatochromism of a pyridinium phenoxide. This parameter mainly reflects the electrophilicity and the H-bond donor activity of the solvent and is generally used when intramolecular bonded systems are studied. Dimroth, K.; Reichardt, C.; Siepmann, T.; Bohlmann, F. Liebigs Ann. Chem. 1963, 661, 1-37
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(1963)
Liebigs Ann. Chem.
, vol.661
, pp. 1-37
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-
Dimroth, K.1
Reichardt, C.2
Siepmann, T.3
Bohlmann, F.4
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167
-
-
0542430115
-
-
The proposed tautomerization is similar to the one that takes place in 2-pyridone
-
The proposed tautomerization is similar to the one that takes place in 2-pyridone: Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Am. Chem. Soc. 1992, 114, 1645-1652
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 1645-1652
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-
Wong, M.W.1
Wiberg, K.B.2
Frisch, M.J.3
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168
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79959503267
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-
Given that the accuracy of our computational method is likely to be around ∼1 kcal/mol, we believe that our calculations are not able to distinguish the difference between the barriers of 1 and 2.
-
Given that the accuracy of our computational method is likely to be around ∼1 kcal/mol, we believe that our calculations are not able to distinguish the difference between the barriers of 1 and 2.
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-
-
-
169
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0011083499
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Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
-
(1988)
Chem. Rev.
, vol.88
, pp. 899-926
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-
Reed, A.E.1
Curtiss, L.A.2
Weinhold, F.3
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170
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0003915529
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-
Theoretical Chemistry Institute, University of Wisconsin: Madison.
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Glendening, E. D.; Badenhoop, J, K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO 5.0; Theoretical Chemistry Institute, University of Wisconsin: Madison, 2001.
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(2001)
NBO 5.0
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-
Glendening, E.D.1
Badenhoop, J.K.2
Reed, A.E.3
Carpenter, J.E.4
Bohmann, J.A.5
Morales, C.M.6
Weinhold, F.7
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171
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79959533711
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-
Bio-Logic Company: Echirolles, France.
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Biokine, User's Manual; Bio-Logic Company: Echirolles, France, 1991.
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(1991)
Biokine, User's Manual
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172
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79959517226
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-
E H+→ Z H+. For this reason we have used c = 0 in our calculations.
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E H+→ Z H+. For this reason we have used c = 0 in our calculations.
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