New Oxidovanadium(IV) Complexes with 2,2′-bipyridine and 1,10-phenathroline Ligands: Synthesis, Structure and High Catalytic Activity in Oxidations of Alkanes and Alcohols with Peroxides
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization of Compounds 1–4a
2.2. Crystal Structures of 3 and 4a
2.3. Oxidation of Alkanes with Peroxides Catalyzed by Complexes 1–4
2.4. Theoretical Mechanistic Study
3. Experimental Section
3.1. Computational Details
Sg + [(–12.21 cal/mol•K) – 0.23(Sg – 12.21 cal/mol•K) + 5.87 cal/mol•K]
3.2. Materials
3.3. Physical Measurements
3.4. X-ray Crystallography
4. Conclusions
5. Syntheses of the Complexes
5.1. Synthesis of [VIVO(bpy)Cl2]n (1)
5.2. Synthesis of [VIVO(phen)Cl2]n (2)
5.3. Synthesis of [VIVO(bpy)Br2]n (3)
5.4. Synthesis of [VIVO(phen)Br2]n (4)
5.5. Oxidation of Alcohols and Hydrocarbons with Peroxides
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: A sample of the catalyst is not available from the authors. |
3 | 4a | |
Crystal Data | ||
Chemical formula | C10H8Br2N2OV | C15H15Br2N3O2V |
Mr | 382.94 | 480.06 |
Crystal system, space group | Monoclinic, P21 | Monoclinic, P21/n |
Temperature (K) | 130 | 150 |
a, b, c (Å) | 7.4626 (3), 17.5643 (7), 9.3510 (4) | 7.1041 (6), 14.0723 (9), 17.2455 (12) |
β (°) | 92.037 (4) | 90.614 (3) |
V (Å3) | 1224.91 (9) | 1724.0 (2) |
µ(mm−1) | 7.31 | 5.22 |
Crystal size (mm) | 0.25 × 0.06 × 0.06 | 0.10 × 0.06 × 0.05 |
Data collection | ||
Diffractometer | New Xcalibur, AtlasS2 | Bruker Apex Duo |
Absorption correction | Multi-scan CrysAlis PRO 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | Multi-scan SADABS (Bruker-AXS, 2004) |
Tmin, Tmax | 0.739, 1000 | 0.545, 0.642 |
Compound 3 | |||
V1—O1 | 1.617 (5) | V2—Br3 | 2.4932 (16) |
V1—O2 | 2.123 (5) | V2—Br4 | 2.4919 (16) |
V1—Br1 | 2.4944 (16) | N1—V1 | 2.124 (7) |
V1—Br2 | 2.5028 (16) | N2—V1 | 2.129 (8) |
V2—O1 i | 2.125 (5) | N3—V2 | 2.124 (8) |
V2—O2 | 1.617 (5) | N4—V2 | 2.136 (8) |
V1—O1—V2 ii | 176.2 (4) | C10—N2—V1 | 125.3 (7) |
V2—O2—V1 | 177.8 (4) | C11—N3—V2 | 125.2 (7) |
C1—N1—V1 | 125.2 (7) | C15—N3—V2 | 115.4 (6) |
C5—N1—V1 | 116.8 (6) | C16—N4—V2 | 115.5 (6) |
C6—N2—V1 | 116.7 (6) | C20—N4—V2 | 124.5 (7) |
Compound 4a | |||
O1—V2 | 1.600 (3) | N2—V2 | 2.121 (3) |
O2—V2 | 1.996 (3) | Br1—V2 | 2.5450 (8) |
N1—V2 | 2.296 (3) | Br2—V2 | 2.5484 (7) |
C14—O2—V2 | 129.3 (3) | C3—N2—V2 | 117.8 (3) |
C1—N1—V2 | 129.6 (2) | C4—N2—V2 | 123.2 (3) |
C2—N1—V2 | 112.6 (3) |
n-Heptane | MeCH | 1,2-cis-DMCH | ||
---|---|---|---|---|
Entry | Catalyst | C(1):C(2):C(3):C(4) | 1°:2°:3° | trans/cis |
1 | 1 | 1.0:5.6:5.8:5.2 | 1.0:5.9:16.0 | 0.84 |
2 | 2 | 1.0:5.6:5.6:5.2 | 1.0:5.3:17.5 | 0.7 |
3 | 3 | 1.0:5.7:6.2:5.6 | 1.0:5.0:12.6 | 0.8 |
4 | 4 | 1.0:5.9:6.2:5.9 | 1.0:5.4:12.9 | 0.9 |
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Fomenko, I.S.; Gushchin, A.L.; Abramov, P.A.; Sokolov, M.N.; Shul'pina, L.S.; Ikonnikov, N.S.; Kuznetsov, M.L.; Pombeiro, A.J.L.; Kozlov, Y.N.; Shul’pin, G.B. New Oxidovanadium(IV) Complexes with 2,2′-bipyridine and 1,10-phenathroline Ligands: Synthesis, Structure and High Catalytic Activity in Oxidations of Alkanes and Alcohols with Peroxides. Catalysts 2019, 9, 217. https://doi.org/10.3390/catal9030217
Fomenko IS, Gushchin AL, Abramov PA, Sokolov MN, Shul'pina LS, Ikonnikov NS, Kuznetsov ML, Pombeiro AJL, Kozlov YN, Shul’pin GB. New Oxidovanadium(IV) Complexes with 2,2′-bipyridine and 1,10-phenathroline Ligands: Synthesis, Structure and High Catalytic Activity in Oxidations of Alkanes and Alcohols with Peroxides. Catalysts. 2019; 9(3):217. https://doi.org/10.3390/catal9030217
Chicago/Turabian StyleFomenko, Iakov S., Artem L. Gushchin, Pavel A. Abramov, Maksim N. Sokolov, Lidia S. Shul'pina, Nikolay S. Ikonnikov, Maxim L. Kuznetsov, Armando J. L. Pombeiro, Yuriy N. Kozlov, and Georgiy B. Shul’pin. 2019. "New Oxidovanadium(IV) Complexes with 2,2′-bipyridine and 1,10-phenathroline Ligands: Synthesis, Structure and High Catalytic Activity in Oxidations of Alkanes and Alcohols with Peroxides" Catalysts 9, no. 3: 217. https://doi.org/10.3390/catal9030217