Iso- and Homeostructuralism of Analogous Ph4E and Ph3E−E‘R3 Compounds (E = C, Si, Ge, Sn, Pb; E‘ = Si, Ge, Sn; R = Me, Ph):  Crystal Structure of 1,1,1-Trimethyltriphenyldistannane

Pa̋rkányi, László; Kàlmán, Alajos; Pannell, Keith H.; Cervantes‐Lee, Francisco; Kapoor, Rupam

doi:10.1021/ic960791z

Cited by 13 publications

(4 citation statements)

References 25 publications

(33 reference statements)

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“…In the former case, the Me 3 E-E 0 Ph 3 dumbbells related by a center of symmetry are antiparallel, whereas in the orthorhombic pair of structures they are stacked in a parallel array. Continuing these investigations, we found that the crystals of Me 3 Ge-GePh 3 (Pá rká nyi et al, 1994), Me 3 Sn-SnPh 3 (Pá rká nyi et al, 1996) and some others, such as Me 3 Pb-SnPh 3 and Me 3 Pb-PbPh 3 (Preut & Huber, 1976), are again trigonal with the space group P " 3 3. A 180 rotation of the R 3 Ge-SnR 0 3 dumbbells, perpendicular to the respective E-E 0 bond, was attributed (Ká lmá n & Pá rká nyi, 1997) to the 0.19 Å difference in the covalent radii of Ge and Sn with respect to those of 0.11 and 0.06 Å observed between the Ge-Si and Pb-Sn pairs, respectively.…”

Section: Introductionsupporting

confidence: 58%

Morphotropism: link between the isostructurality, polymorphism and (stereo)isomerism of organic crystals

Kàlmán

2005

Acta Crystallogr Sect B

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An ongoing analysis of the supramolecular self-assembly of disubstituted cycloalkanes has led to the discovery of seven packing patterns built up from hydrogen-bonded homo- and heterochiral chains of racemic molecules, associated in either antiparallel or parallel arrays [Kálmán et al. (2001). Acta Cryst. B57, 539-550]. Two further patterns have been revealed in the close packing of analogous alicyclic beta-amino acids [Fábián et al. (2005). Cryst. Growth Des. 5, 773-782]. Since each pattern is represented by at least one crystal structure, the chemical similarity and crystallographic forms of these crystals have facilitated the recognition that these patterns differ by one or two rotation(s) of the common motifs (e.g. dimers, tetramers, helices etc.), or the whole pattern may rotate through 180 degrees in an oblique unit cell. Such non-crystallographic--with the exception of polymorphism--virtual rotations as a whole may be denoted by the expression morphotropism. According to Kitaigorodskii [(1961), Organic Chemical Crystallography, pp. 222-231. New York: Consultants Bureau], morphotropism is an attempt to keep the packing coefficient above 0.6 whenever there are alternative possibilities for the structures of closely related molecules. It has been found that crystals of stereoisomers are also frequently related by such virtual rotations. Similarly, non-crystallographic rotations effect bridges between homostructural crystals [Kálmán et al. (1993b). Acta Cryst. B49, 1039-1049] and occasionally hallmark the polymorphism of organic compounds [Kálmán et al. (2003) J. Am. Chem. Soc. 125, 34-35]. In polymorphs, however, such rotations really transform one molecule into another in order to achieve a better packing mediated by solvents, temperature etc.

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Section: Introductionsupporting

confidence: 58%

Morphotropism: link between the isostructurality, polymorphism and (stereo)isomerism of organic crystals

Kàlmán

2005

Acta Crystallogr Sect B

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“…Comparison of the Sn-C and Sn-Sn bond lengths in 2 with those observed in other sterically crowded molecules shows that they display some, but not an excessive, elongation. For instance, comparison of the Sn-C distances for the tin methyl groups in Me 3 SnSnPh 3 (Sn-C(Me) ) 2.138(5) Å), 17 shows that they are ca. 0.03 Å shorter than the Sn-C(Me) bonds (ca.…”

Section: Resultsmentioning

confidence: 99%

Characterization of the Sterically Encumbered Terphenyl-Substituted Species 2,6-Trip₂H₃C₆S̈n−Sn(Me)₂C₆H₃-2,6-Trip₂, an Unsymmetric, Group 14 Element, Methylmethylene, Valence Isomer of an Alkene, Its Related Lithium Derivative 2,6-Trip₂H₃C₆(Me)₂Sn−Sn(Li)(Me)C₆H₃-2,6-Trip₂, and the Monomer Sn(t-Bu)C₆H₃-2,6-Trip₂ (Tri

Eichler

Power

2000

Inorg. Chem.

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The reaction of the recently reported sterically encumbered terphenyl tin(II) halide species Sn(Cl)C6H3-2,6-Trip2 (Trip = C6H2-2,4,6-i-Pr3), 1, with 1 equiv of MeLi or MeMgBr afforded 2,6-Trip2H3C6Sn-Sn(Me)2C6H3-2,6-Trip2, 2, which is the first stable group 14 element methylmethylene (i.e., CH3CH) analogue of ethylene (H2CCH2). Reaction of 1 with 1.5 equiv of MeLi yielded the stannylstannate species 2,6-Trip2H3C6(Me)2Sn-Sn(Li)(Me)-C6H3-2,6-Trip2, 3, whereas reaction of 1 with 1 equiv of t-BuLi gave the heteroleptic stannanediyl monomer Sn(t-Bu)C6H3-2,6-Trip2 (4). The compounds 2-4 were characterized by 1H, 13C (7Li, 3 only), and 119Sn NMR spectroscopy in solution and by UV-vis spectroscopy. The X-ray crystal structures of 2-4 were also determined. The formation of the stannylstannanediyl 2 instead of the expected symmetrical, valence isomer "distannene" form (Sn(Me)C6H3-2,6-Trip2)2, 6, is explained through the ready formation of LiSn(Me)2C6H3-2,6-Trip2, 5, which reacts rapidly with 1 to produce 2 which can then react with a further equivalent of MeLi to give 3. The stability of singly bonded 2 in relation to the formally doubly bonded 6 was rationalized on the basis of the difference in the strength of their tin-tin bonds. In contrast to the methyl derivatives, the reaction of 1 with t-BuLi proceeded smoothly to give the monomeric compound 4. Apparently, the formation of a t-Bu analogue of 5 was prevented by the more crowding t-Bu group. Compound 2 is also the first example of a stable molecule with bonding between a two-coordinate, bivalent tin and four-coordinate tetravalent tin. Both compounds 2 and 3 display large J 119Sn-119Sn couplings between their tin nuclei and the tin-tin bond lengths in 2 (2.8909(2) A) and 3 (2.8508(4) A) are relatively normal despite the presence of the sterically crowding terphenyl substituents.

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“…The first has two RCOO" groups in a syn-syn arrangement bridging a pair of SnC 2 moieties [3][4][5][6]8]. The third group has no bridging ligands [9,11,[13][14][15]18,19,21,22,24,28], The third group has no bridging ligands [9,11,[13][14][15]18,19,21,22,24,28],…”

Section: Dimers Containing a Tin-tin Bondmentioning

confidence: 99%

“…In the third group of Sn 2 +6 derivatives, there are several examples with two tetrahedral tin atoms held together by a direct Sn-Sn bond; SnC 3 [9,11,[13][14][15]18,22,24,28], SnC 2 CI [13,22] and SnC 2 Br [18,21]. In another example [18a] two trigonal-bipyramidal units, SnC 2 NCI are linked, and overall the range of values for the Sn-Sn bond are from 275.9(4) to 303.…”

Section: Fig 1 Structure Of Sn 2^-ac) 2 (Ph) 4 [3] Fig 2 Structurmentioning

confidence: 99%

Tin Organometallic Compounds: Classification and Analysis of Crystallographic and Structural Data: Part Ii. Dimeric Derivatives

Holloway¹,

Melnı́k²

2000

Main Group Metal Chemistry

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This review covers the crystallographic data of organotin compounds containing two tin centres, with a view to identifying correlations between properties and structure. Almost two hundred and fifty such compounds are included, of which almost thirty contain Sn 2 +6 units with a direct Sn-Sn bond, the shortest being 269.1(1) pm. There are ten compounds with tin in the +2 oxidation state, with a shortest Sn(ll)-Sn(ll) bond distance of 276.4(2) pm. The remainder of the compounds contain tin(IV), and the shortest Sn(IV)-Sn(IV) distance is 294 pm. The predominant geometries for tin(IV) are tetrahedral and trigonal bipyramidal. Distortion and cis-trans isomerism are found, the former being most common. In one example of distortion isomerism crystallographically independent molecules occur within the same unit. Several types of bridging are observed between the tin centres. Relationships between bond distances, ligand size and angles are discussed in the respective sections. The most common bridge donor atom is oxygen. The most common carbon donor ligands are phenyl and methyl groups.

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Iso- and Homeostructuralism of Analogous Ph₄E and Ph₃E−E‘R₃ Compounds (E = C, Si, Ge, Sn, Pb; E‘ = Si, Ge, Sn; R = Me, Ph): Crystal Structure of 1,1,1-Trimethyltriphenyldistannane

Cited by 13 publications

References 25 publications

Morphotropism: link between the isostructurality, polymorphism and (stereo)isomerism of organic crystals

Morphotropism: link between the isostructurality, polymorphism and (stereo)isomerism of organic crystals

Tin Organometallic Compounds: Classification and Analysis of Crystallographic and Structural Data: Part Ii. Dimeric Derivatives

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