Enantiomeric-Enriched Ferrocenes: Synthesis, Chiral Resolution, and Mathematic Evaluation of CD-chiral Selector Energies with Ferrocene-Conjugates
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. Enantiomeric Resolution
2.3. Calculations
2.4. Crystal Structures
3. Experimental Section
3.1. Methods and Materials
3.2. General Procedure
3.3. Calculations
3.4. Crystallography
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–7 are available from the authors. |
No | Molecule | Enantiomeric Excess, ee % (a) | [α] | Concentration, mole·L−1 |
---|---|---|---|---|
(S)-1 | FcCH(CH3)-3,5-Me2Pz | 93 | +78.75 | 0.40 (benzene) |
(S)-2 | FcCH(CH3)OH | 97 | +30.75 | 0.60 (methanol) |
(S)-3 | FcCH(CH3)-3-CF3,5-CH3 Pz | not determined | +12.00 | 0.30 (benzene) |
(S)-4 | FcCH(CH3)-3-CF3,5-CF3 Pz | not determined | +14.30 | 0.18 (benzene) |
(S)-5 | FcCH(CH3)Pz | 95 | +16.50 | 0.70 (benzene) |
No | Molecule (a) | Chiral Stationary Phase (b) | Separation Factor, α | ΔE, kcal/M |
---|---|---|---|---|
1 | FcCH(CH3)-3,5-Me2Pz | β-CD | 1.059 | 3.85 |
2 | FcCH(CH3)OH | β-CD | 1.133 | 4.89 |
3 | FcCH(CH3)-3-CF3,5-CH3Pz | β-CD | 1.153 | 4.94 |
4 | FcCH(CH3)-3-CF3,5-CF3Pz | β-CD | 1.182 | 5.25 |
5 | FcCH(CH3)Pz | β-CD (c) | 1.195 | 5.58 |
6 | γ-CD (d) | 1.308 | 6.20 | |
7 | γ-CD (d) | 1.385 | 7.59 |
System | E, a.u. | μ, D | HOMO, a.u. | LUMO, a.u. |
---|---|---|---|---|
(R)-1-β-CD | −5167.4437 | 4.25 | −0.19354 | −0.02009 |
(S)-1-β-CD | −5167.4481 | 6.25 | −0.20897 | −0.03714 |
1 | (S)-1 | |
---|---|---|
Diffractometer | Bruker Smart APEX II | CAD4 Enraf-Nonius |
T, K | 120 | 293 |
Empirical formula | C17H20FeN2 | C17H20FeN2 |
Formula weight | 308.20 | 308.20 |
Crystal system | Orthorhombic | Orthorhombic |
Space group, Z | P212121, 4 | P212121, 4 |
Densitycalc. (g·cm−3) | 1.396 | 1.346 |
a (Å) | 7.8662(5) | 7.9670(16) |
b (Å) | 8.9661(5) | 8.9670(18) |
c (Å) | 20.7985(13) | 21.291(4) |
V (Å3) | 1466.90(15) | 1521.0(5) |
2θmax (°) | 60.12 | 49.91 |
F(000) | 648 | 648 |
Reflections collected | 19,371 | 1649 |
Independent reflections (R(int)) | 4301 (0.0542) | 1565 (0.0108) |
Number of reflections with I > 2σ(I) | 3766 | 1364 |
Parameters | 185 | 184 |
Flack | 0.467(18) | −0.02(4) |
Linear absorption (cm−1) | 10.19 | 9.83 |
Goodness-of-fit (GOF) | 1.010 | 0.998 |
R1 (I > 2σ(I)) | 0.0330 | 0.0396 |
wR2 (all reflections) | 0.0698 | 0.1054 |
ρmin/ρmax, e | 0.338/−0.397 | 0.366/−0.661 |
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Snegur, L.V.; Borisov, Y.A.; Kuzmenko, Y.V.; Davankov, V.A.; Ilyin, M.M.; Ilyin, M.M., Jr.; Arhipov, D.E.; Korlyukov, A.A.; Kiselev, S.S.; Simenel, A.A. Enantiomeric-Enriched Ferrocenes: Synthesis, Chiral Resolution, and Mathematic Evaluation of CD-chiral Selector Energies with Ferrocene-Conjugates. Molecules 2017, 22, 1410. https://doi.org/10.3390/molecules22091410
Snegur LV, Borisov YA, Kuzmenko YV, Davankov VA, Ilyin MM, Ilyin MM Jr., Arhipov DE, Korlyukov AA, Kiselev SS, Simenel AA. Enantiomeric-Enriched Ferrocenes: Synthesis, Chiral Resolution, and Mathematic Evaluation of CD-chiral Selector Energies with Ferrocene-Conjugates. Molecules. 2017; 22(9):1410. https://doi.org/10.3390/molecules22091410
Chicago/Turabian StyleSnegur, Lubov V., Yurii A. Borisov, Yuliya V. Kuzmenko, Vadim A. Davankov, Mikhail M. Ilyin, Mikhail M. Ilyin, Jr., Dmitry E. Arhipov, Alexander A. Korlyukov, Sergey S. Kiselev, and Alexander A. Simenel. 2017. "Enantiomeric-Enriched Ferrocenes: Synthesis, Chiral Resolution, and Mathematic Evaluation of CD-chiral Selector Energies with Ferrocene-Conjugates" Molecules 22, no. 9: 1410. https://doi.org/10.3390/molecules22091410