Preparative, spectroscopic, and structural studies on some new silylamines

Nobert W. Mitzel; Jürgen Riede; Annette Schier; Martin Paul; Hubert Schmidbaur

doi:10.1002/cber.19931260910

Preparative, spectroscopic, and structural studies on some new silylamines

Nobert W. Mitzel, Jürgen Riede, Annette Schier, Martin Paul, Hubert Schmidbaur

Department of Chemistry

Technical University of Munich

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

The synthesis and characterization of two complete series of benzyl(phenylsilyl)amines (PhH₂Si)_x(PhH₂C)_{3 — x}N, benzyl(p‐tolylsilyl)amines (p‐H₃CC₆H₄H₂Si)_x(PhH₂C)_{3 — x}N, and of bis‐(p‐tolylsilyl)amine are described. The compounds have been prepared from the corresponding amines and chlorosilanes with triethylamine as the auxiliary base. Bis(phenylsilyl)(trimethylsilyl)amine, (PhH₂Si)₂NSiMe₃ (10), was obtained by the reaction of lithium bis(phenylsilyl)amide with chlorotrimethylsilane. Crystal structure analyses reveal that dibenzyl(p‐tolylsilyl)amine (7) and 10 contain planar nitrogen atoms. Heteronuclear NMR spectra (¹H, ¹³C, ¹⁵N, and ²⁹Si) have been measured for all compounds. The ¹⁵N chemical shifts are shown to be sensitive to variations of the geometry at the nitrogen atom. The coupling constants ¹J(¹⁵N²⁹Si) show a linear correlation with the N—Si bond lengths.

Original language	English
Pages (from-to)	2027-2032
Number of pages	6
Journal	Chemische Berichte
Volume	126
Issue number	9
DOIs	https://doi.org/10.1002/cber.19931260910
State	Published - Sep 1993

Keywords

Nitrogen configuration
Silazanes
Silylamines

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10.1002/cber.19931260910

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title = "Preparative, spectroscopic, and structural studies on some new silylamines",

abstract = "The synthesis and characterization of two complete series of benzyl(phenylsilyl)amines (PhH2Si)x(PhH2C)3 — xN, benzyl(p‐tolylsilyl)amines (p‐H3CC6H4H2Si)x(PhH2C)3 — xN, and of bis‐(p‐tolylsilyl)amine are described. The compounds have been prepared from the corresponding amines and chlorosilanes with triethylamine as the auxiliary base. Bis(phenylsilyl)(trimethylsilyl)amine, (PhH2Si)2NSiMe3 (10), was obtained by the reaction of lithium bis(phenylsilyl)amide with chlorotrimethylsilane. Crystal structure analyses reveal that dibenzyl(p‐tolylsilyl)amine (7) and 10 contain planar nitrogen atoms. Heteronuclear NMR spectra (1H, 13C, 15N, and 29Si) have been measured for all compounds. The 15N chemical shifts are shown to be sensitive to variations of the geometry at the nitrogen atom. The coupling constants 1J(15N29Si) show a linear correlation with the N—Si bond lengths.",

keywords = "Nitrogen configuration, Silazanes, Silylamines",

author = "Mitzel, {Nobert W.} and J{\"u}rgen Riede and Annette Schier and Martin Paul and Hubert Schmidbaur",

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AU - Mitzel, Nobert W.

AU - Riede, Jürgen

AU - Schier, Annette

AU - Paul, Martin

AU - Schmidbaur, Hubert

PY - 1993/9

Y1 - 1993/9

N2 - The synthesis and characterization of two complete series of benzyl(phenylsilyl)amines (PhH2Si)x(PhH2C)3 — xN, benzyl(p‐tolylsilyl)amines (p‐H3CC6H4H2Si)x(PhH2C)3 — xN, and of bis‐(p‐tolylsilyl)amine are described. The compounds have been prepared from the corresponding amines and chlorosilanes with triethylamine as the auxiliary base. Bis(phenylsilyl)(trimethylsilyl)amine, (PhH2Si)2NSiMe3 (10), was obtained by the reaction of lithium bis(phenylsilyl)amide with chlorotrimethylsilane. Crystal structure analyses reveal that dibenzyl(p‐tolylsilyl)amine (7) and 10 contain planar nitrogen atoms. Heteronuclear NMR spectra (1H, 13C, 15N, and 29Si) have been measured for all compounds. The 15N chemical shifts are shown to be sensitive to variations of the geometry at the nitrogen atom. The coupling constants 1J(15N29Si) show a linear correlation with the N—Si bond lengths.

AB - The synthesis and characterization of two complete series of benzyl(phenylsilyl)amines (PhH2Si)x(PhH2C)3 — xN, benzyl(p‐tolylsilyl)amines (p‐H3CC6H4H2Si)x(PhH2C)3 — xN, and of bis‐(p‐tolylsilyl)amine are described. The compounds have been prepared from the corresponding amines and chlorosilanes with triethylamine as the auxiliary base. Bis(phenylsilyl)(trimethylsilyl)amine, (PhH2Si)2NSiMe3 (10), was obtained by the reaction of lithium bis(phenylsilyl)amide with chlorotrimethylsilane. Crystal structure analyses reveal that dibenzyl(p‐tolylsilyl)amine (7) and 10 contain planar nitrogen atoms. Heteronuclear NMR spectra (1H, 13C, 15N, and 29Si) have been measured for all compounds. The 15N chemical shifts are shown to be sensitive to variations of the geometry at the nitrogen atom. The coupling constants 1J(15N29Si) show a linear correlation with the N—Si bond lengths.

KW - Nitrogen configuration

KW - Silazanes

KW - Silylamines

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DO - 10.1002/cber.19931260910

M3 - Article

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EP - 2032

JO - Chemische Berichte

JF - Chemische Berichte

IS - 9

ER -

Preparative, spectroscopic, and structural studies on some new silylamines

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Keywords

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