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6,6′-((Ethane-1,2-diylbis(azanediyl))bis(methylene))bis(2,4-bis(2-phenylpropan-2-yl)phenolate)zirconium(IV) Dichlorido

by
Joana Hipólito
1,
Ana M. Martins
1,* and
Luis G. Alves
2,*
1
Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal
2
Centro de Química Estrutural, Institute of Molecular Sciences, Associação do Instituto Superior Técnico para a Investigação e Desenvolvimento, Av. Rovisco Pais 1, 1049-003 Lisboa, Portugal
*
Authors to whom correspondence should be addressed.
Molbank 2022, 2022(4), M1511; https://doi.org/10.3390/M1511
Submission received: 2 November 2022 / Revised: 22 November 2022 / Accepted: 24 November 2022 / Published: 1 December 2022
(This article belongs to the Section Structure Determination)
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Abstract

:
The salan zirconium complex of formula [(H2N2O2)ZrCl2] (H2N2O2H2 = HOPh’CH2NH(CH2)2NHCH2Ph’OH, where Ph’ = 2,4-(CMe2Ph)C6H2) was synthesized and fully characterized by NMR and single-crystal X-ray diffraction. The solid-state molecular structure of [(H2N2O2)ZrCl2] shows distorted octahedral geometry around the zirconium center with the salan ligand adopting a β-Λ-cis conformation.

1. Introduction

Over the past decades, early transition metal complexes supported by salan ligands have been used in a wide variety of catalytic transformations [1,2,3,4,5,6]. Most of those applications are focused on olefin [7,8,9] and cyclic esters polymerization [10,11,12], olefin epoxidation [13,14,15] and sulfoxidation reactions [16,17,18,19]. Metal complexes supported by salan-type ligands have also been studied as cytotoxic agents [20,21,22,23,24]. Due to the importance of these type of compounds in chemical and biological fields, we present here the synthesis and structural characterization of a new salan zirconium complex.

2. Results and Discussion

The treatment of ZrCl4 with the sodium salt H2N2O2Na2 prepared in situ by the reaction of two equiv. of NaH with H2N2O2H2, 1 [6], afforded the complex [(H2N2O2)ZrCl2], 2, (H2N2O2H2 = HOPh’CH2NH(CH2)2NHCH2Ph’OH, where Ph’ = 2,4-(CMe2Ph)C6H2), as shown in Scheme 1.
The 1H NMR spectrum of 2 (see Figure S1), featuring two AX spin systems assigned to the NCH2CPhO groups and two AX spin systems due to the NCH2CH2N protons, is consistent with a C1-symmetric species, as confirmed by its solid-state molecular structure determined by single-crystal X-ray diffraction (see discussion below). The 13C{1H} NMR spectrum of 2 is in accordance with the pattern observed in the proton NMR spectrum (see Figure S2).
Crystals of 2 suitable for single-crystal X-ray diffraction were obtained from a diethyl ether solution at −20 °C. Compound 2 crystallized with one diethyl ether molecule in the asymmetric unit. Crystal data for 2 (C4H10O) (M = 979.24 g/mol): monoclinic, space group P21/n (no. 14), a = 15.475(2) Å, b = 11.729(1) Å, c = 28.533(3) Å, β = 93.430(4)°, V = 5169.6(10) Å3, Z = 4, T = 150(2) K, μ(MoKα) = 0.360 mm−1, Dcalc = 1.258 g/cm3, 54,545 reflections measured (3.075° ≤ Θ ≤ 27.914°), 12,300 unique (Rint = 0.0878, Rsigma = 0.0781) were used in all calculations. The final R1 was 0.0736 (I > 2σ(I)) and wR2 was 0.1161 (all data). The ORTEP diagram of the solid-state molecular structure of 2 is shown in Figure 1. Complex 2 displays distorted octahedral geometry around the zirconium center with the salan ligand adopting a β-Λ-cis conformation [25]. The equatorial plane is defined by the Cl(1) atom and the N(1), N(2) and O(1) atoms of the salan ligand, and the axial positions of the octahedron are occupied by the Cl(2) atom and the O(2) atom of the salan ligand. The overall bond distances and angles determined for 2 are within the ranges reported for other zirconium(IV) complexes supported by salan ligands described in the literature [26,27,28,29]. The solid-state molecular structure of 2 is similar to the one of the salan titanium(IV) complex [(H2N2O2)TiCl2] already reported [6].

3. Materials and Methods

3.1. General Considerations

Compound 1 was prepared according to previously published procedures [6,19]. Commercial NaH (60% dispersion in mineral oil) was washed several times with n-hexane and dried under vacuum. All other reagents were of commercial grade and used without purification. All manipulations were performed under an atmosphere of dry oxygen-free nitrogen by means of standard Schlenk and glovebox techniques. Solvents were pre-dried using 4 Å molecular sieves and refluxed over sodium-benzophenone under an atmosphere of N2 and collected by distillation. Deuterated solvents were dried with 4 Å molecular sieves and freeze-pump-thaw degassed prior to use. NMR spectra were recorded in a Bruker AVANCE II 300 MHz spectrometer, at 296 K, referenced internally to residual proton–solvent (1H) or solvent (13C) resonances, and reported relative to tetramethylsilane (0 ppm). 2D NMR experiments, such as 1H-13C HSQC and 1H-1H COSY, were performed in order to make all the assignments. Elemental analyses (C, H and N) were performed in a Fisons CHNS/O analyser Carlo Erba Instruments EA-1108 equipment at the Laboratório de Análises do Instituto Superior Técnico.

3.2. Synthesis and Characterization

[(H2N2O2)ZrCl2], 2: A THF solution of 1 (0.54 g, 0.72 mmol) was added to a suspension of NaH (0.04 g, 1.72 mmol) in the same solvent at −30 °C. The temperature was allowed to rise slowly to room temperature and the mixture was further stirred for 3 h at 50 °C. The colorless solution obtained was filtered and added to a THF solution of ZrCl4 (0.17 g, 0.72 mmol). The yellow solution formed was stirred for 16 h at room temperature. The solvent was evaporated to dryness and the residue was extracted with toluene. Evaporation of the solvent to dryness led to a yellow crystalline solid. Yield: 24% (0.15 g, 0.17 mmol). 1H NMR (THF-d8, 300.1 MHz, 296 K): δ (ppm) 7.48 (d, 2H, 3JH-H = 7 Hz, CHPh), 7.37–7.21 (overlapping, 11H total, CHPhO and CHPh), 7.16–7.09 (overlapping, 5H total, CHPh and CHPhO), 6.92 (s, 1H, CHPhO), 6.60 (d, 2H, 3JH-H = 7 Hz, CHPh), 6.48 (s, 1H, CHPhO), 6.43–6.36 (overlapping, 2H total, CHPhO and CHPh), 5.44 (b, 1H, NH), 4.42 (d, 1H, 2JH-H = 14 Hz, NCH2CPhO), 3.88 (b, 1H, NH), 3.72 (d, 1H, 2JH-H = 14 Hz, NCH2CPhO), 3.14 (b, 1H, NCH2CPhO), 2.67 (d, 1H, 2JH-H = 11 Hz, NCH2CPhO), 2.42 (d, 1H, 2JH-H = 11 Hz, NCH2CH2N), 2.32 (d, 1H, 2JH-H = 12 Hz, NCH2CH2N), 1.97–1.90 (overlapping, 7H total, NCH2CH2N and C(CH3)2), 1.68–1.67 (overlapping, 12H, (C(CH3)2), 1.50 (s, 3H, C(CH3)2), 1.22 (s, 3H, C(CH3)2), 1.11 (m, 1H, NCH2CH2N). 13C{1H} NMR (THF-d8, 75.5 MHz, 296 K) δ (ppm) 156.6 (OCPhO), 156.4 (OCPhO), 152.4 (CPh), 152.0 (CPh), 151.3 (CPh), 151.2 (CPh), 142.3 (CPhO), 142.1 (CPhO), 141.6 (CPhO), 137.2 (CPhO), 137.0 (CPhO), 136.5 (CPhO), 128.7 (CHPh), 128.6 (CHPh), 128.5 (CHPh and NCH2CPhO), 128.4 (CHPhO), 127.9 (CHPh), 127.6 (CHPh), 127.5 (NCH2CPhO), 127.4 (CHPhO), 127.0 (CHPh), 126.6 (CHPh), 126.5 (CHPhO), 126.3 (CHPh), 126.2 (CHPh), 125.5 (CHPh), 125.4 (CHPhO), 124.4 (CHPh), 54.9 (NCH2CPhO), 52.9 (NCH2CH2N), 52.2 (NCH2CH2N), 49.9 (NCH2CPhO), 43.3 (C(CH3)2), 42.7 (C(CH3)2), 42.6 (C(CH3)2), 34.7 (C(CH3)2), 32.5 (C(CH3)2), 31.5 (C(CH3)2), 31.4 (C(CH3)2), 27.5 (C(CH3)2), 26.2 (C(CH3)2). Anal. calcd. for C52H58Cl2N2O2Zr: C, 69.00; H, 6.46; N, 3.09; found: C, 69.09; H, 6.52; N, 3.07.

3.3. General Procedure for Single-Crystal X-ray Crystallography

Suitable crystals of compound 2 were coated and selected in Fomblin® oil under an inert atmosphere of nitrogen. Crystals were then mounted on a loop external to the glovebox environment and data were collected using graphite monochromated Mo-Kα radiation (λ = 0.71073 Å) on a Bruker AXS-KAPPA APEX II diffractometer (Bruker AXS Inc., Madison, WI, USA) equipped with an Oxford Cryosystem open-flow nitrogen cryostat. Cell parameters were retrieved using Bruker SMART software and refined using Bruker SAINT on all observed reflections [30]. Absorption corrections were applied using SADABS [31]. The structures were solved by direct methods using SIR97 [32]. Structure refinement was carried out using SHELXL-2018/3 [33]. These programs are part of the WinGX software package version 1.80.01 [34] system of programs. Hydrogen atoms of the NH groups were located in the electron density map. The other hydrogen atoms were inserted in calculated positions and allowed to refine in the parent carbon atoms.

Supplementary Materials

1H and 13C{1H} NMR spectra of compound 2 are presented as supporting information in Figures S1 and S2, respectively. Crystallographic and experimental details of data collection and crystal structure determinations of compound 2 are available in Table S1. Data for compound 2 were deposited in the Cambridge Crystallographic Data Centre (CCDC) under the deposit number 2209906 and can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (accessed on 23 November 2022).

Author Contributions

J.H. performed the synthesis and characterization of the compounds; L.G.A. performed the single-crystal X-ray diffraction studies and wrote the manuscript; A.M.M. supervised the experiments and revised the manuscript. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by Fundação para a Ciência e a Tecnologia, Portugal (UID/QUI/00100/2019, UIDB/00100/2020, UIDP/00100/2020, LA/P/0056/2020 and CATSUS PD/BD/114399/2016).

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

Not applicable.

Conflicts of Interest

The authors declare no conflict of interest.

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Molbank 2022 m1511 sch001 550
Scheme 1. Synthetic route for the preparation of [(H2N2O2)ZrCl2], 2.
Scheme 1. Synthetic route for the preparation of [(H2N2O2)ZrCl2], 2.
Molbank 2022 m1511 sch001
Molbank 2022 m1511 g001 550
Figure 1. ORTEP diagram of [(H2N2O2)ZrCl2], 2, showing thermal ellipsoids at a 40% probability level. Hydrogen atoms and the co-crystalized diethyl ether molecule were omitted for clarity. The selected bond lengths (Å) and angles (°) are: Zr(1)-N(1) 2.369(2), Zr(1)-N(2) 2.326(2), Zr(1)-O(1) 1.945(2), Zr(1)-O(2) 1.979(2), Zr(1)-Cl(1) 2.4534(6), Zr(1)-Cl(2) 2.4902(6); N(1)-Zr(1)-N(2) 74.39(7), N(1)-Zr(1)-O(1) 78.32(6), N(2)-Zr(1)-Cl(1) 102.81(5), O(1)-Zr(1)-Cl(1) 104.17(5), O(2)-Zr(1)-Cl(2) 155.90(5).
Figure 1. ORTEP diagram of [(H2N2O2)ZrCl2], 2, showing thermal ellipsoids at a 40% probability level. Hydrogen atoms and the co-crystalized diethyl ether molecule were omitted for clarity. The selected bond lengths (Å) and angles (°) are: Zr(1)-N(1) 2.369(2), Zr(1)-N(2) 2.326(2), Zr(1)-O(1) 1.945(2), Zr(1)-O(2) 1.979(2), Zr(1)-Cl(1) 2.4534(6), Zr(1)-Cl(2) 2.4902(6); N(1)-Zr(1)-N(2) 74.39(7), N(1)-Zr(1)-O(1) 78.32(6), N(2)-Zr(1)-Cl(1) 102.81(5), O(1)-Zr(1)-Cl(1) 104.17(5), O(2)-Zr(1)-Cl(2) 155.90(5).
Molbank 2022 m1511 g001
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Hipólito, J.; Martins, A.M.; Alves, L.G. 6,6′-((Ethane-1,2-diylbis(azanediyl))bis(methylene))bis(2,4-bis(2-phenylpropan-2-yl)phenolate)zirconium(IV) Dichlorido. Molbank 2022, 2022, M1511. https://doi.org/10.3390/M1511

AMA Style

Hipólito J, Martins AM, Alves LG. 6,6′-((Ethane-1,2-diylbis(azanediyl))bis(methylene))bis(2,4-bis(2-phenylpropan-2-yl)phenolate)zirconium(IV) Dichlorido. Molbank. 2022; 2022(4):M1511. https://doi.org/10.3390/M1511

Chicago/Turabian Style

Hipólito, Joana, Ana M. Martins, and Luis G. Alves. 2022. "6,6′-((Ethane-1,2-diylbis(azanediyl))bis(methylene))bis(2,4-bis(2-phenylpropan-2-yl)phenolate)zirconium(IV) Dichlorido" Molbank 2022, no. 4: M1511. https://doi.org/10.3390/M1511

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