A variable temperature NMR analysis and resonance assignment of the Grubbs second generation catalyst

Swart, Marthinus Rudi; Twigge, Linette; Marais, Charlene; Bezuidenhoudt, Barend C. B.

doi:10.1016/j.poly.2018.06.024

Cited by 6 publications

(16 citation statements)

References 22 publications

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“…In order to be able to observe through space association between hydrogens and thus obtain structural information about the GII ‐cresol complex, all resonances in the 1 H NMR spectrum were assigned to protons by means of 2D NMR spectroscopy (Supplementary Information). The GII allocations in DCM‐d 2 closely resembled those previously reported in CDCl 3 [31] …”

Section: Resultssupporting

confidence: 83%

“…The observation of a cation with m/z 453, [11 + H], by MALDI-TOF MS corroborated this postulate (Figure 1c). Similar 31 P NMR resonances were observed when PCy 3 was exposed to methyl acrylate (3 b) and LiCl in CH 2 Cl 2 for 4 hours. 31 P NMR analysis of a β-methylstyrene (2 b) -methyl acrylate (1 b) (1 : 1) reaction mixture after being heated for 1 hour at 40°C in the presence of GII and p-cresol (12) (4 eq.…”

Section: Resultssupporting

confidence: 67%

“…[41] Similar results were encountered when the NMR spectroscopic analyses were performed at room temperature in CDCl 3 . [31,34] The formation of carbyne complex (25) was, however, not observed (no resonance in the vicinity of a carbon triple bonded to ruthenium; δ C 248 for GI), [33] although trace amounts of a new type of benzylidene carbon was detected at δ c 287.6 (vs δ c 293.7 for the benzylidene carbon of GII under the same conditions). It could therefore be concluded that the bis (cresolate) complex 23, if formed, did not decompose to carbyne entity 25 under the prevailing conditions.…”

Section: Resultsmentioning

confidence: 99%

“…Figure2 31. P NMR of Grubbs II catalyst with different reagent combinations: GII (0.024 mmol) in dry DCM (5 mL) with p-cresol (0.094 mmol, 4 eq.…”

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confidence: 99%

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Olefin Metathesis, p‐Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces

et al. 2021

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p‐Cresol as additive to the Grubbs second generation catalyst (GII) allows the cross‐metathesis of acrylates with prop‐1‐en‐1‐ylbenzenes under conditions that only give the prop‐1‐en‐1‐ylbenzene self‐metathesis product in the absence of cresol. NMR and IR spectroscopy, MALDI‐TOF MS and XPS supported the formation of a ruthenium benzylidene with hydrogen bonds between p‐cresol and the chloride ligands of GII. XPS furthermore confirmed p‐cresol to increase the binding energies of the GII Ru 3d5/2, 3d3/2, 3p3/2 and 3p1/2 photoelectron lines, whereas 1H NMR spectroscopy indicated the carbene carbon and hydrogen to be shielded. It is thus postulated that p‐cresol allows for more facile interaction between electron‐deficient compounds and the ruthenium benzylidene by decreasing the electron density on the metal center and increasing the electron density on the carbene.

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Section: Resultssupporting

confidence: 83%

Section: Resultssupporting

confidence: 67%

Section: Resultsmentioning

confidence: 99%

“…Figure2 31. P NMR of Grubbs II catalyst with different reagent combinations: GII (0.024 mmol) in dry DCM (5 mL) with p-cresol (0.094 mmol, 4 eq.…”

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confidence: 99%

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Olefin Metathesis, p‐Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces

et al. 2021

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“…The 1 H and 13 C Nuclear Magnetic Resonance NMR resonances of 3 (see Figs. 2 and 3 ) were allocated in analogy to those of Grubbs second generation catalyst ( 1 ) [ 2 , 3 ] and by means of Heteronuclear single quantum coherence spectroscopy (HSQC) and Heteronuclear Multiple Bond Correlation (HMBC) experiments and are summarised in Table 1 . The HSQC and HMBC spectra of complex ( 3 ) are presented in Fig.…”

Section: Data Descriptionmentioning

confidence: 99%

NMR data of a Grubbs 2nd generation catalyst p-cresolate derivative

et al. 2021

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The data presented in this article is related to the research article entitled “Spectroscopic characterisation of Grubbs 2 nd generation catalyst and its p -cresol derivatives” (Swart et al. 2021). The 1D and 2D NMR characterisation data of the p- cresol derivative of the Grubbs 2 nd generation catalyst, where one of the chloride ligands is replaced by the p -cresolate to form a Ru-O coordination compound ( 3 ) is reported. The characterization data include information obtained from 1 H, 13 C, Heteronuclear Single Quantum Coherence (HSQC), Heteronuclear Multiple Bond Correlation (HMBC), Homonuclear Correlation Spectroscopy (COSY), Nuclear Overhauser Effect (NOE) and Distortionless Enhancement by Polarization Transfer (DEPT) NMR spectroscopy.

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The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2018

Herndon

2019

Coordination Chemistry Reviews

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A variable temperature NMR analysis and resonance assignment of the Grubbs second generation catalyst

Cited by 6 publications

References 22 publications

Olefin Metathesis, p‐Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces

Olefin Metathesis, p‐Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces

NMR data of a Grubbs 2nd generation catalyst p-cresolate derivative

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2018

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