Unusual Hexacoordination in a Triorganotin Fluoride Supported by Intermolecular Hydrogen Bonds. Crystal and Molecular Structures of 1-Aza-5-stanna-5-halotricyclo[3.3.3.01.5]undecanes N(CH2CH2CH2)3SnF.cntdot.H2O and N(CH2CH2CH2)3SnX (X = Cl, Br, I)

Kolb, Ute; Draeger, M.; Dargatz, M.; Jurkschat, Klaus

doi:10.1021/om00006a031

Cited by 60 publications

(41 citation statements)

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“…In addition, the increase of the coordination on the path of the tetrahedron → trigonal bipyramid transition leads, as a rule, to: a) increase of 1 J( 119 Sn-13 C) with the atoms that become equatorial; b) decrease of 1 J( 119 Sn-13 C) with the atoms that become axial. Such a change in the spin-spin coupling constants agrees with the different contributions from the s-orbital of the tin atom to the respective Sn-C bonds with change in the hybridization as a result of intramolecular attack of the donor atom [3,8,55].…”

Section: Nmr Spectroscopysupporting

confidence: 71%

“…This results in the formation of high yields of unsymmetrically substituted methylhalo derivatives [4,55]. Methylfluorostannocane 16q was isolated in the form of an adduct with one water molecule, the source of which was atmospheric moisture.…”

Section: Q 10pmentioning

confidence: 99%

“…Methylfluorostannocane 16q was isolated in the form of an adduct with one water molecule, the source of which was atmospheric moisture. Attempts to crystallize the anhydrous compound under absolutely inert conditions were unsuccessful [55].…”

Section: Q 10pmentioning

confidence: 99%

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Metallocanes of group 14 elements 2. Derivatives of tin (Review)

Selina

Karlov

Lermontova

et al. 2007

Chem Heterocycl Compd

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Section: Nmr Spectroscopysupporting

confidence: 71%

Section: Q 10pmentioning

confidence: 99%

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Metallocanes of group 14 elements 2. Derivatives of tin (Review)

Selina

Karlov

Lermontova

et al. 2007

Chem Heterocycl Compd

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“…Similar behavior is encountered in the crystals of tin analogs. 5-Methyl-1-aza-5-stannabicyclo[3.3.3]undecane (refcode FEWXOU) [79] and its 5-fluoro [91], 5-chloro [92], 5-bromo [91], and 5-iodo [91] analogs (refcodes ZANKEE, DAYMUL, ZANKOO, ZANKUU, respectively) all show close Sn···N contacts (Fig. 14).…”

Section: Nitrogen Atoms As Tb Acceptorsmentioning

confidence: 99%

Close contacts involving germanium and tin in crystal structures: experimental evidence of tetrel bonds

et al. 2018

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Modeling indicates the presence of a region of low electronic density (a Bσ-hole^) on group 14 elements, and this offers an explanation for the ability of these elements to act as electrophilic sites and to form attractive interactions with nucleophiles. While many papers have described theoretical investigations of interactions involving carbon and silicon, such investigations of the heavier group 14 elements are relatively scarce. The purpose of this review is to rectify, to some extent, the current lack of experimental data on interactions formed by germanium and tin with nucleophiles. A survey of crystal structures in the Cambridge Structural Database is reported. This survey reveals that close contacts between Ge or Sn and lone-pair-possessing atoms are quite common, they can be either intra-or intermolecular contacts, and they are usually oriented along the extension of the covalent bond formed by the tetrel with the most electron-withdrawing substituent. Several examples are discussed in which germanium and tin atoms bear four carbon residues or in which halogen, oxygen, sulfur, or nitrogen substituents replace one, two, or three of those carbon residues. These close contacts are assumed to be the result of attractive interactions between the involved atoms and afford experimental evidence of the ability of germanium and tin to act as electrophilic sites, namely tetrel bond (TB) donors. This ability can govern the conformations and the packing of organic derivatives in the solid state. TBs can therefore be considered a promising and robust tool for crystal engineering.

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“…Only a small number of compounds containing bulky ligands, e.g., Sn[C(SiMe 2 Ph) 3 ]Me 2 F [5], Sn[C(SiMe 3 ) 3 ]Ph 2 F [5], Sn[C 6 H 2 (Me 3 -2,4,6) 3 ]Me 2 F [6] and Sn(CH 2 SiMe 3 ) 3 F [7], with a four-coordinated tin central atom, are monomeric with a Sn-F terminal single bond distance about 1.96 Å [8]. There is an example of the compound (Sn[(CH 2 CH 2 CH 2 ) 3 N]FÁH 2 O) with an intramolecular Sn-N interaction; the structure of this compound in the solid state has been established as tetrameric due to intermolecular fluorine and hydrogen bridges, respectively, and monomeric in solution [9]. Recently, we have reported triorganotin(IV) fluorides of general formula L CN R 2 SnF, where L CN is {2-[(CH 3 ) 2 NCH 2 ]C 6 H 4 } À and R is alkyl (Me, nBu, tBu) or aryl (Ph) groups of different steric bulk and electronic properties [10].…”

Section: Introductionmentioning

confidence: 99%