Crystal and molecular structure of β-1-phenylsilatrane, C12H17NSi

Parkanyi, L.; Simon, Kálmán; Nagy, J.

doi:10.1107/s0567740874007060

Cited by 58 publications

(21 citation statements)

References 2 publications

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“…The X-ray analysis of 12a confirmed the distorted trigonal bipyramidal geometry around silicon atom (O1−Si−O2 = 84.1°, O1−Si−O3 = 165.8°, O2−Si−O4 = 128.7°) with a methyl and an allyl groups at the trans -positions to each other regarding the five-membered ring as illustrated in Figure . The bond lengths of Si−O2 (1.731(4) Å), Si−O3 (1.739(4) Å), and Si−O4 (1.656(4) Å) are comparable with those in the penta- and hexacoordinate silicate anions having catecholato ligand .…”

Section: Resultsmentioning

confidence: 81%

Synthesis and Reactions of Neutral Hypercoordinate Allylsilicon Compounds Having a Tropolonato Ligand

et al. 1996

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A novel intramolecular allylic migration from silicon to carbon was observed during the reaction of allylmethyldichlorosilane with tropolone in the presence of triethylamine to give an isomeric mixture of pentacoordinate silicon compounds having allylated tropolonato ligand. The molecular structure of the major isomer was determined by X-ray analysis. Reaction of diprenyldichlorosilane with tropolone at low temperature (−35 °C) gave the first hexacoordinate allylsilicon compound, diprenylbis(tropolonato)silicon, which underwent the allylic migration at room temperature to give the neutral pentacoordinate allylic silicon compound. The activation parameters for the rearrangement in CDCl3 were determined by NMR to be ΔH ⧧ = 77.6 kJ/mol and ΔS ⧧ = −60.3 J/(mol·K). Facile allylation of aldehyde was performed with the neutral pentacoordinate allylic silicon compounds to give the corresponding homoallylic alcohols in good yields (70−90%) at room temperature without any catalyst.

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Section: Resultsmentioning

confidence: 81%

Synthesis and Reactions of Neutral Hypercoordinate Allylsilicon Compounds Having a Tropolonato Ligand

et al. 1996

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“…The formal substitution of the Me 3 Si group by a hydrogen atom in compound 5 sharply shortens the transannular Si←N ax distance (2.132(4) Å for N(CH 2 CH 2 NH) 3 Si−C 6 H 5 ). 12 The Si−C distance observed in 5 (1.910(2) Å) is somewhat longer than that in the closely related 1-phenylsilatrane N(CH 2 CH 2 O) 3 Si−C 6 H 5 (1.882(6), 1.894(5), and 1.908(4) Å for different crystal modifications) − but slightly shorter than that in 1-phenylazasilatrane N(CH 2 CH 2 NH) 3 Si−C 6 H 5 (1.922(5) Å) . Analogously, the Ge−C bond (1.985(2) Å) for compound 8 is also longer than that in 1-phenylgermatrane N(CH 2 CH 2 O) 3 Ge−C 6 H 5 (1.947(6) Å) …”

Section: Resultsmentioning

confidence: 91%

Azametallatranes of Group 14 Elements. Syntheses and X-ray Studies

et al. 2002

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Syntheses of a series of the title compounds, viz., N(CH2CH2NR)3M−X (1, M = Si, X = Me, R = SiMe3; 2, M = Si, X = Et, R = SiMe3; 3, M = Si, X = n-Bu, R = SiMe3; 4, M = Si, X = vinyl, R = SiMe3; 5, M = Si, X = Ph, R = SiMe3; 6, M = Ge, X = Me, R = SiMe3; 7, M = Ge, X = n-Bu, R = SiMe3; 8, M = Ge, X = Ph, R = SiMe3; 9, M = Sn, X = n-Bu, R = SiMe3; 10, M = Sn, X = Ph, R = SiMe3; 11, M = Si, X = vinyl, R = Me; 12, M = Ge, X = Me, R = Me) by the reaction of X−MCl3 with N(CH2CH2NSiMe3Li)3 or with N(CH2CH2NMeLi)3 are reported. Reactions of the novel compounds X−Ge(NMe2)3 (15, X = Ph; 16, X = 1-naphthyl; 17, X = 9-antracenyl; 18, X = 9-phenantrenyl) with N(CH2CH2NHMe)3 or N(CH2CH2NH2)3 resulted in new 1-arylazagermatranes, N(CH2CH2NMe)3Ge−X (19, X = Ph; 20, X = 1-naphthyl; 21, X = 9-antracenyl; 22, X = 9-phenantrenyl) and N(CH2CH2NH)3Ge−X (23, X = Ph; 24, X = 1-naphthyl; 25, X = 9-phenantrenyl), respectively. 1-Phenylazagermatrane (23) is transformed to 8 by treatment with n-BuLi/Me3SiCl. Composition and structures of novel compounds were established by elemental analyses, 1H, 13C, and 29Si NMR spectroscopy, and mass spectrometry. The X-ray structural studies of 10 and 19 clearly indicated the presence of a transannular interaction M←Nax for both compounds. quasi-Azametallatranes 5 and 8 possess extremely long M←Nax distances.

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“…97 In spite of having a completely staggered conformation with the SiO 3 moiety, CF 3 shows a rotation of 9.41 around the Si-C bond axis in 1-trifluoromethylsilatrane (77). 57 The crystal structure of 3-isothiocyanatopropylsilatrane (133) shows a strong hydrogen bonding between the O atom of silatrane and most acidic hydrogen atoms present at C9 bonded to the -NCS group (Fig. 13).…”

Section: Crystallographic Studiesmentioning

confidence: 99%

“…Silatranes having six atoms in the arms of silatranyl ring show a different bond length of Si-N when compared with their analogues with five atoms in the tricyclic silatranyl ring. [130][131][132][133][134] The longer bond distance is observed due to a restricted approach of N towards the Si atom, which is attributed to the associated ring constraints. Due to larger ring system and flexibility of compounds 236-251, the N atom is free to move but in fivemembered tricyclic silatranes the N atom is forced to approach towards the Si, which results in the formation of strong transannular bonds.…”

Section: Crystallographic Studiesmentioning

confidence: 99%

Silatranes: a review on their synthesis, structure, reactivity and applications

2011

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This critical review summarizes progress of the rapidly developing and very active field of silatrane chemistry. The first part of the review deals with general synthetic approaches used to synthesize different silatranes. The most interesting feature of silatranes, i.e., variation of Si-N bond length on the basis of the axial substituent of Si, and other structural features, are described in the second part with special emphasis on crystallographic and theoretical studies. It is followed by a discussion on the reactivity of various silatranes. Silatranes have now gained acceptance for a wide variety of applications which are summarized in the last section of review. Some of them have extensive interest due to their medical use to heal wounds or stimulate hair-growth (pilotropic activity), biological properties, pharmacological properties e.g. antitumor, anticancer, antibacterial, anti-inflammatory, fungicidal activity, stimulating effect in animal production and seed germination effects. The review focuses on the extended potential of silatranes in sol-gel processes, mesoporous zeotypes, atomic force microscopy, commercial products such as adhesion promoters, polymer formation and rubber compositions. This critical review will be helpful for general researchers, experts, advanced undergraduates and newcomers working on silatrane chemistry as this review presents greater emphasis on synthesis and characterization, structural properties, reactivity and applications of silatranes in the field of biology, material science, sol-gel chemistry, pharmaceutics, agriculture and medicine (311 references).

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Crystal and molecular structure of β-1-phenylsilatrane, C12H17NSi

Cited by 58 publications

References 2 publications

Synthesis and Reactions of Neutral Hypercoordinate Allylsilicon Compounds Having a Tropolonato Ligand

Synthesis and Reactions of Neutral Hypercoordinate Allylsilicon Compounds Having a Tropolonato Ligand

Azametallatranes of Group 14 Elements. Syntheses and X-ray Studies

Silatranes: a review on their synthesis, structure, reactivity and applications

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