Force field parameters for aminoorganosilanes

Lactamomethylsilanes of γ-butyrolactam, δ-valerolactam, ε-caprolactam, and 1-isoindolinone (phthalimidine) with up to three methyl moieties were synthesized according to the chemical formula Me x SiLac (4-x) (x = 0, 1, 2, and 3). Using the lactams as starting materials four synthetic routes were tested: salt elimination, transsilylation, transamination, and metallation of the lactames followed by reaction 377 with methylchlorosilanes. All products were analyzed by NMR ( 1 H, 13 C and 29 Si) and RAMAN spectroscopy. Selected solid products were crystallized and the molecular structure was determined by single-crystal X-ray diffraction. The reactivity of the lactamomethylsilanes towards phenylisocyanate and CO 2 was studied.Si-O bond but less reactive than a Si-Cl bond. The Si-N bond is prone towards hydrolysis and alkoholysis. Additionally, some substances containing Si-N bonds react with heteroallenes like CO 2 and isocyanates via insertion reactions yielding useful products such as ureas, carbamates, and polysiloxanes, among others. [23][24][25][26] Therefore, in the presented study we have synthesized lactamomethylsilanes of the type Me x SiLac (4-x) (x = 0, 1, 2, and 3) [Lac = γ-butyrolactam, δ-valerolactam, εcaprolactam, and 1-isoindolinone (phthalimidine)] in order to investigate their structures and reactivities.

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“…The Si–N bond lengths are between 1.742(2) to 1.745(2) Å. This is in the range for typical Si–N bond lengths . The Si–C bond is 1.834(3) Å.…”

Section: Resultsmentioning

confidence: 75%

“…Many aminosilanes were synthesized via this route in nonpolar solvents like n ‐hexane or n ‐pentane , . The used lactams as well as the synthesized lactamomethylsilanes are not soluble in these solvents.…”

Section: Resultsmentioning

confidence: 99%

Lactamomethylsilanes – Synthesis, Structures, and Reactivity towards CO₂ and Phenylisocyanate

Herbig

Böhme

Kroke

2019

Zeitschrift anorg allge chemie

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Insertion of CO2 and related heteroallenes into the Si–N-bond of methyl(N-morpholino)silanes

Herbig

Böhme

Kroke

2018

Inorganica Chimica Acta

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New cyclic and spirocyclic aminosilanes

Herbig

Scholz

Böhme

et al. 2021

Main Group Metal Chemistry

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New cyclic and spirocyclic aminosilanes were synthesised using ethylenediamine, 2-aminobenzylamine, 1,8-diaminonaphthalene, o-phenylenediamine, and trans-cyclohexane-1,2-diamine as starting material. These diamines were converted into aminosilanes using silicon tetrachloride and dimethyldichlorosilane directly and via the N,N’-bis(trimethylsilylated) amino derivatives. 15 new compounds of the type (diamino)(SiMe3)2, (diamino)2Si, (diamino)SiMe2, and (diamino)SiCl2 have been prepared. The formation of two cyclotrisilazane derivatives was observed starting from (N,N’-2-aminobenzylamino)dichlorosilane by trimerisation. All synthesised compounds have been characterised with NMR-, Raman-, or IR-spectroscopy, mass-spectrometry, and boiling or melting point. Single-crystal X-ray structure analyses of several derivatives have been performed. The degree of substitution with trimethylsilyl groups in the final compounds depends on the ring size of the spirocycles. It was shown with quantum chemical calculations on the M062X/6-31G(d) level that trimethylsilyl groups have a stabilising effect on 5-membered ring systems and a destabilising effect on 6-membered rings in these compounds.

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Force field parameters for aminoorganosilanes

Cited by 4 publications

References 21 publications

Lactamomethylsilanes – Synthesis, Structures, and Reactivity towards CO₂ and Phenylisocyanate

Lactamomethylsilanes – Synthesis, Structures, and Reactivity towards CO₂ and Phenylisocyanate

Insertion of CO2 and related heteroallenes into the Si–N-bond of methyl(N-morpholino)silanes

New cyclic and spirocyclic aminosilanes

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Force field parameters for aminoorganosilanes

Cited by 4 publications

References 21 publications

Lactamomethylsilanes – Synthesis, Structures, and Reactivity towards CO2 and Phenylisocyanate

Lactamomethylsilanes – Synthesis, Structures, and Reactivity towards CO2 and Phenylisocyanate

Insertion of CO2 and related heteroallenes into the Si–N-bond of methyl(N-morpholino)silanes

New cyclic and spirocyclic aminosilanes

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Product

Resources

About

Lactamomethylsilanes – Synthesis, Structures, and Reactivity towards CO₂ and Phenylisocyanate

Lactamomethylsilanes – Synthesis, Structures, and Reactivity towards CO₂ and Phenylisocyanate