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Article

Enantiomeric-Enriched Ferrocenes: Synthesis, Chiral Resolution, and Mathematic Evaluation of CD-chiral Selector Energies with Ferrocene-Conjugates

1
A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., 119991 Moscow, Russian
2
N.I. Pirogov Russian National Research Medical University, 1 Ostrovityanov St., 117997 Moscow, Russian
3
Moscow Institute of Steel and Alloys National University of Science and Technology, 4 Leninskii Av., 119049 Moscow, Russian
*
Author to whom correspondence should be addressed.
Molecules 2017, 22(9), 1410; https://doi.org/10.3390/molecules22091410
Received: 14 July 2017 / Revised: 23 August 2017 / Accepted: 24 August 2017 / Published: 25 August 2017
(This article belongs to the Special Issue Chirality in Health and Environment: Recent developments)
Enantiomeric-enriched ferrocene-modified pyrazoles were synthesized via the reaction of the ferrocene alcohol, (S)-FcCH(OH)CH3 (Fc = ferrocenyl), with various pyrazoles in acidic conditions at room temperature within several minutes. X-ray structural data for racemic (R,S)-1N-(3,5-dimethyl pyrazolyl)ethyl ferrocene (1) and its (S)-enantiomer (S)-1 were determined. A series of racemic pyrazolylalkyl ferrocenes was separated into enantiomers by analytical HPLC on β- and γ-cyclodextrins (CD) chiral stationary phases. The quantum chemical calculations of interaction energies of β-CD were carried out for both (R)- and (S)-enantiomers. A high correlation between experimental HPLC data and calculated interaction energies values was obtained. View Full-Text
Keywords: ferrocene; pyrazoles; enantioenriched compounds; enantiomers; X-ray crystallography; HPLC; cyclodextrin; quantum chemical calculations ferrocene; pyrazoles; enantioenriched compounds; enantiomers; X-ray crystallography; HPLC; cyclodextrin; quantum chemical calculations
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MDPI and ACS Style

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

AMA Style

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 Style

Snegur, 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

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