A crystalline stibinidene with a triplet ground state

doi:10.21203/rs.3.rs-2083038/v1

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A crystalline stibinidene with a triplet ground state

https://doi.org/10.21203/rs.3.rs-2083038/v1

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Pnictinidenes (R-E; E = P, As, Sb or Bi) are long-sought reactive species, which are isoelectronic to carbenes. They feature either a singlet or triplet ground state depending on the electronic property of the substituents. Although isolable singlet carbenes and fairly stable triplet carbenes are well-documented, triplet pnictinidenes isolable under standard laboratory conditions remain elusive. Herein we report the isolation, characterizations and reactivity studies of a free stibinidene supported by a hydrindacene ligand. X-ray crystallographic analysis shows that it contains a one-coordinate antimony atom featuring a Sb–C single bond. Magnetometric investigations, in conjunction with highly correlated wavefunction based ab initio calculations unequivocally demonstrate that the stibinidene features a triplet electronic ground state.

Physical sciences/Chemistry/Inorganic chemistry/Organometallic chemistry

Physical sciences/Chemistry/Inorganic chemistry/Chemical bonding

Pnictinidenes (R-E; E = P, As, Sb or Bi), compounds containing a monosubstituted pnictogen atom in the oxidation state of +1, are isoelectronic to the well-known carbenes. They feature either a singlet or triplet electronic ground state (Fig. 1a). Computational work reveals that π-donating substituents, such as R₂N^– or R₂P^–, attached to the pnictogen atom significantly stabilize the singlet ground state, whereas σ-type ligands, such as hydride, alkyl and phenyl ligands, favor the triplet ground state^1,2. The chemistry of carbenes is well-documented, and a variety of singlet carbenes have been isolated in the condensed phase^3,4, such as the widely used N-heterocyclic carbenes⁵ and cyclic (alkyl)(amino) carbenes⁶. However, triplet carbenes are more difficult to obtain due to the diradical character. Until now only a few fairly stable, but still not ‘bottle-able’ triplet carbenes have been characterized in solutions by the group of Tomioka^7-9.

Despite the isoelectronic relationship, the isolation of free pnictinidenes is much more challenging owing to the high propensity of self-aggregation^10-12, thereby complexation to Lewis acids or Lewis bases is required for the isolation^13-17. Bertrand and coworkers achieved a major breakthrough by isolating hitherto the solo example of a singlet phosphinophosphinidene I supported by an extremely bulky diaminophosphino ligand (Fig. 1b)¹⁸, and a similar strategy was used to synthesize a singlet nitrene¹⁹. Although not structurally characterized by X-ray crystallography, its identification as a free phosphinidene was unambiguously authenticated by nuclear magnetic resonance (NMR) spectroscopy and reactivity studies. The unoccupied 3p-orbital at the terminal phosphorus center is substantially stabilized by the π-donation from the lone pair of electrons at the phosphinyl center as shown in the bonding diagram II, resulting in a pronounced P–P multiple bond character and a singlet electronic ground state.

Contrastingly, triplet pnictinidenes isolable under standard laboratory conditions remain elusive, inasmuch as such species have only been spectroscopically characterized in organic solvent matrices^20-22 or in the gas phase^23-25. Recently, we used sterically encumbered hydrindacene ligands to successfully obtain several highly reactive main group species²⁶^,²⁷. These findings therefore prompted us to investigate whether a similar strategy could be utilized to isolate long-sought triplet pnictinidenes. Herein we report the synthesis, X-ray crystallographic and spectroscopic characterizations, and reactivity studies of an isolable pnictinidene, i.e. stibinidene M^sFluind^*-Sb 4 (Fig. 1c). Magnetometric analyses, in conjunction with highly correlated wavefunction based ab initio calculations unequivocally demonstrate that it has a triplet electronic ground state. Key to the successful preparation of the stibinidene is the steric effect of the supporting ligand, kinetically impeding it from dimerization.

Synthesis and characterization of distibene 2 and stibinidene 4

Firstly, we tested the reduction of antimony(III) dichloride 1 (Supplementary Information Fig. S1), supported by the hydrindacene ligand M^sFluid^t^Bu with 2 molar equivalents of KC₈ in THF at room temperature. However, distibene 2 was isolated as purplish crystals in 46% yield from the reaction mixture (Fig. 2a). Compound 2 contains a Sb=Sb double bond with a distance of 2.7223(5) Å as revealed by single-crystal X-ray diffraction (SC-XRD) analysis (Supplementary Information Fig. S2), which is the longest one among the reported distibenes^28-32. The flanking fluorenyl substituents are highly twisted to adopt a suitable orientation that allows the interaction between the two Sb atoms. We thus reasoned that increasing the steric hindrance at the fluorenyl moieties might prevent the formation of the Sb=Sb double bond and permit the access of the corresponding free stibinidene.

Accordingly, we synthesized the antimony(III) precursor M^sFluind^*-SbBr₂ 3 with a slightly more steric hindered ligand. To our delight, debromination of 3 with 2 molar equivalents of KC₈ in THF at room temperature afforded stibinidene 4 as yellow crystals in 11% yield (Fig. 2a). When Jones’ magnesium dimer LMgMgL (L = CH(MeCNMes)₂; Mes = 2,4,6-Me₃C₆H₂) was used as a reducing agent³³, a higher yield of 31% was obtained. Compound 4 is moderately soluble in benzene and n-hexane, but highly soluble in toluene and THF. It is highly air-sensitive, but is quite stable in solution and the solid state under an inert atmosphere at room temperature. Moreover, no decomposition was observed after heating at 80 ^oC for 1 hour in deuterated benzene solution, demonstrating the high thermal stability. The range of ¹H and ¹³C chemical shifts for 4 increases dramatically (δ –2.25-14.49 and –31.5-277.3 ppm for ¹H and ¹³C{¹H,¹³C} NMR spectra, respectively) in comparison to those of diamagnetic compounds, suggestive of a paramagnetic nature. To rule out the presence of hydrogen atoms at the Sb center in 4, we synthesized M^sFluind^*-SbH₂ 4H₂ through the reaction of 3 with 2 molar equivalents of Li[BEt₃H]. Contrastingly, the ¹H and ¹³C{¹H,¹³C} NMR spectra of 4H₂ exhibit signals at the normal diamagnetic windows, and the proton signals of the SbH₂ moiety is observed at δ 1.82 ppm. Moreover, the Fourier transform infrared spectrum of 4H₂ shows a stretching band at 1886 cm^–1 for the Sb–H bond, which is close to that in ArSbH₂ (1875 cm^–1; Ar = 2,6-Trip₂-C₆H₃; Trip = 2,4,6-iPr₃C₆H₂)³⁴, while no band is observed in this region for 4. These results unambiguously show that no hydrogen atom is attached to the Sb atom in 4.

SC-XRD characterization of 4

Molecular structure of 4 was determined by SC-XRD analysis (Fig. 2b). It crystallizes in monoclinic space group C2/c, and features C_2v symmetry. In comparison, 4H₂ crystallizes in monoclinic space group P2₁/c (Supplementary Information Fig. S3). The Sb atom in 4 is only bound to the C atom of the central phenyl ring of the supporting ligand, and resides in the center of the ligand pocket well-shielded by the two flanking fluorenyl moieties. The Sb1–C1 distance (2.148(3) Å) is comparable to that in Terp^MesSb=SbTerp^Mes (2.169(4) Å; Terp^Mes = 2,6-Mes₂-C₆H₃)¹¹, suggesting its single bond character. Noteworthy, there is no noticeable intermolecular Sb•••Sb interaction in the solid state, and the Sb atoms are well-separated by the ligand backbones. The closest distance between the Sb center and the C atom of the flanking flurorenyl moieties is as long as 3.250(3) Å, which is far beyond the sum of the single bond covalent radii for the C and Sb atoms (2.15 Å)³⁵, but shorter than the sum of the van der Waals radii (3.76 Å)^36,37, indicative of the presence of noticeable non-covalent bonding interactions. Therefore, compound 4 can be described as a free stibinidene containing a one-coordinate antimony atom.

Magnetic characterization of 4

To explore the electronic structure of 4, we carried out variable-temperature (T) magnetic susceptibility (χ) measurements on a solid sample with a superconducting quantum interference device (SQUID). As shown in Fig. 2c, the χT product increases with temperature, and does not become saturated even at 300 K. The observed variation of χT with respect to T cannot be interpreted as the temperature-independent paramagnetism of a singlet ground state (Supplementary Information Fig. S4). Therefore, it can be concluded that 4 has a triplet ground state, although its magnetic property is distinctly different from those usually measured for S = 1 complexes. As elaborated in Supplementary Information Fig. S5, this peculiar behavior is due to the presence of a gigantic zero-field splitting (ZFS) in 4. For the same reason, its isotropic g factor (g_iso) cannot be accurately determined, as χT at the high-temperature saturation limit is proportional to . In view of the fact that triplet nitrenes and phosphinidenes typically features g_iso = 2.0³⁸, we thus fixed g_iso to be 2.0 in the simulation of the SQUID data using a standard S = 1 spin Hamiltonian. The rhombicity parameter (E/D) was fixed to be 0, because 4 possesses a bonding situation similar to those of closely related Sb diatomic molecules (see below) and hence effective axial symmetry. A reasonable fit gave an axial ZFS parameter of D = 1030±20 cm^-1, comparable to those measured for SbH (655 cm^-1), SbF (816 cm^-1), and SbCl (796 cm^-1)³⁹. Furthermore, D was found to be not very sensitive to g_iso; when g_isovaries from 2.00 to 1.90, D slightly decreases from 1030 to 930 cm^–1.

Theoretical calculations of 4

To shed more light on the bonding of 4, we first carried out noncovalent interaction (NCI) analyses⁴⁰ with DFT calculations employing the scalar relativistic second-order Douglas-Kroll-Hess Hamiltonian⁴¹. The NCI plot (Supplementary Information Fig. S6) showed that the interactions between the Sb center and the flanking fluorenyl functionalities of M^sFluid^* primarily originate from van der Waals interactions. We then performed completely active space self-consistent field (CASSCF)/second order N electron valence perturbation theory (NEVPT2) computations on simplified model 4ʹ in which the substituents on the supporting ligand were replaced by hydrogen atoms. To properly describe the covalent bond between the Sb atom and the central phenyl (Ph) moiety in 4, the active space was chosen to distribute 12 electrons into 11 orbitals including Sb–C σ and σ*, Sb 5s and 5p, and six Ph π and π* orbitals. As shown in Fig. 3a, theoretical results revealed that the triplet ground state of 4ʹ features a leading electron configuration of (Sb 5s)²(Ph π_1,2,3)⁶(Sb–C σ_z)²(Sb 5p_x)¹(Sb 5p_y)¹(Ph π^*_4,5,6)⁰(Sb–C σ^*_z)⁰ that accounts for 86% of the wavefunction, and is 15.7 kcal/mol below the lowest-energy S = 0 state that represents the corresponding closed-shell singlet with either Sb 5p_x or 5p_y orbitals being doubly occupied. Therefore, for the S = 1 ground state there exists only one σ-bond formed by the Sb 5p_z and ipso C 2p_z atomic orbitals, congruent with the estimated Mayer Sb–C_ipso bond order of 0.94, while the remaining Sb 5p_x and 5p_y orbitals are essentially nonbonding and nearly degenerate. These findings reflect that the interaction of the Sb 5p_x with the Ph π system is almost negligible. As such, according to the first Hund’s rule, 4ʹ energetically favors a triplet ground state, in analogy to diatomic Sb molecules (SbH, SbF, and SbCl)³⁹. Following this reasoning, the Sb 5p_x and 5p_y orbitals contribute almost equally to the total spin population, thereby leading to donut-like positive spin density around the Sb center (Fig. 3b). Consequently, the Sb center was computed to possess a spin population of 1.97, whereas that of the entire phenyl ring is merely 0.01. Of note, the negative spin population (–0.11) found for the ipso C atom stems from the spin polarization of the Ph π system and Sb–C_ipso σ bonding orbital induced by unpaired electrons populating the Sb 5p_xand 5p_yorbitals. The ab initio calculations gave g_iso = 1.96, D = 940 cm^–1 and E/D = 0.02 for 4ʹ. Given the estimated g_iso factor being slightly different from that employed in the simulation, the predicted D value is in reasonable agreement with the experiment. Finally, the diradical nature deduced for 4 rationalizes why the formation of 2 via a dimerization process of the species generated by dehalogenation of 1 has a great driving force of ~50 kcal/mol and no detectable activation barrier (Supplementary Information Fig. S7).

Reactivity studies of 4

To have a better understanding of the chemical property of 4, we further performed experimental reactivity studies (Fig. 4). Firstly, we carried out the reactions with a Lewis acid and a Lewis base to probe the ambiphilic character. Mixing of 4 with Fe₂(CO)₉ in n-hexane at room temperature afforded a deep brown solution immediately, and stibinidene-iron complex M^sFluid^*-Sb→Fe(CO)₄ (5) was isolated in 30% yield. Complex 5 features a singlet ground state as shown by NMR spectroscopy. The stabilization of the singlet state by coordination to transition metal fragments has also been observed for phosphinidene complexes, attributing to the substantial stabilization of the unoccupied p_π acceptor orbital through π-back-donation from the transition metal centers as rationalized by theoretical calculations⁴². The reaction of 4 with 1,3,4,5-tetramethyl-imidazolin-2-ylidene (I^Me4) afforded base-stabilized stibinidene 6. The complexation to both Lewis acid and base reveals the ambiphilic nature of 4. Furthermore, the reactions with unsaturated substrates have also been examined. 4 smoothly reacted with 2,3-dimethyl-1,3-butadiene and 4-tetrabutylphenylacetylene to furnish antimony-substituted five-membered and three-membered heterocycles 7 and 8 via [1+4] and [1+2] cycloadditions, respectively, reminiscent of the reactivity of transient phosphinidene species^43,44.

In summary, this work demonstrates that free triplet stibinidene M^sFluid^*-Sb 4 can be isolated in the condensed phase at room temperature despite the diradical character. It features a leading electron configuration of (Sb 5s)²(Sb–C σ_z)²(Sb 5p_x)¹(Sb 5p_y)¹(Sb–C σ^*_z)⁰, and the Sb center possesses a spin population of 1.97. The M^sFluid^* supporting ligand offers the necessary steric hindrance that effectively impedes the stibinidene to dimerize. Reactivity studies disclosed the ambiphilic character of 4 as evidenced by its complexation to the Lewis acidic Fe(CO)₄ fragment and the Lewis basic N-heterocyclic carbene. Moreover, it undergoes cycloadditions with unsaturated substrates, such as diene and alkyne, to afford Sb-substituted heterocycles.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant No: 22071164), Suzhou Science & Technology NOVA Program (Grant: ZXL2022445).

Author contributions

G.T. conceived and supervised the project. M.W. and H.L. synthesized and characterized the compounds. D.W. and Y.H. collected the single-crystal X-ray diffraction data. S.Y. supervised magnetometric measurements and theoretical research. W.C. carried out magnetometric measurements and theoretical calculations. G.T. and S.Y. wrote the manuscript, which was reviewed and edited with input from all authors. M.W. H.L. and W.C. contributed equally to this work.

Additional information: Authors declare that they have no competing interests. X-ray data are available free of charge from the Cambridge crystallographic Data Centre under reference numbers CCDC 2203580 (1), 2203581 (2), 2203582 (4), 2203583 (4H₂), 2203584 (5), 2203585 (6), 2203586 (7), 2203587 (8). All other experimental, spectroscopic, crystallographic, and computational data are included in the supplementary information.

There is NO Competing Interest.

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A crystalline stibinidene with a triplet ground state

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