Exoditopic receptors II: Synthesis and x-ray crystal structure of a disilamacrocycle bearing two bipyridine units

Kaes, Christian; Hosseini, Mir Wais; Ruppert, Romain; Cian, André De; Fischer, Jean

doi:10.1016/0040-4039(94)85369-x

Cited by 34 publications

(9 citation statements)

References 23 publications

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“…The axial Si−C Ph distance in 1 (1.867(3) Å) appears to be somewhat shorter than the corresponding equatorial bond length (1.876(3) Å). Both compare well to the mean Si−C Ph bond length (1.875 (average) Å) in other cyclic , and acyclic , derivatives of diphenylsilane. The C Ph −Si−C Ph angle in 1 is 110.3(1)° (exp) or 110.2° (theory) and falls in the range of 106.5° and 112.1° observed in other diphenylsilane derivatives.…”

Section: Resultssupporting

confidence: 64%

Synthesis, Strain, Conformational Analysis, and Molecular and Crystal Structures of 1,1,4,4-Tetraphenyl-1,4-disilacyclohexane and 1,1,4,4-Tetraphenyl-1,4-disilacyclohexa-2,5-diene

1998

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Hydrogenation of 1,1,4,4-tetraphenyl-1,4-disilacyclohexa-2,5-diene (2) to 1,1,4,4-tetraphenyl-1,4-disilacyclohexane (1) provides an efficient new route to 1,4-disilacyclohexanes with isolated overall yields 10 times higher than previously available syntheses. Molecular and crystal structures of 1 and 2 determined by single-crystal X-ray diffraction show that the saturated compound 1 adopts the ideal chairlike conformation, while the unsaturated analogue 2 has a planar 1,4-disilacyclohexa-2,5-diene ring. Ab initio geometry optimizations and vibrational frequency calculations at the 3-21G*/SCF level of theory confirm that the orientations of the phenyl rings observed in 1 represents the global minimum on the potentialenergy surface. Calculations of the transition state for the phenyl ring rotations in 1 reveal a barrier height of ∆G q ) 4.09 kcal/mol. Energy profiles of chairlike and boatlike distortions of 1,4-disilacyclohexa-2,5-diene (12) were calculated and compared with the observed deviation from planarity in other derivatives of 12. Calculation of ring strain energies revealed that diene 12 and its saturated analogue 1,4-disilacyclohexane (4) are almost strain free (1.2 and 0.7 kcal/mol, respectively), resembling their carbon analogues.

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Section: Resultssupporting

confidence: 64%

Synthesis, Strain, Conformational Analysis, and Molecular and Crystal Structures of 1,1,4,4-Tetraphenyl-1,4-disilacyclohexane and 1,1,4,4-Tetraphenyl-1,4-disilacyclohexa-2,5-diene

1998

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“…Tetradentate exohomoditopic ligands have been reported. [2][3][4][5] In this vein, we investigated the substitution of two hydroxy groups in the 1,3-positions by two sulfanyl groups on p-tertbutylcalix [4]arene. 6 We report here the first synthesis of p-tertbutyl-1,3-dihydroxy-2,4-disulfanylcalix [4]arene 7 and of its monomercury complex.…”

mentioning

confidence: 99%

Synthesis and structural studies on p-tert-butyl-1,3-dihydroxy-2,4-disulfanylcalix[4]arene and its mercury complex

Delaigue¹,

Hosseini²,

Kyritsakas³

et al. 1995

J. Chem. Soc., Chem. Commun.

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“…In the solid state compound 212 [332] adopts a centrosymmetric cyclophane type structure in which two bipyridine units are almost parallel and face oriented. The distances between two bipyridine units and two silicon atoms are 3.5 and 10.8 Ä, respectively.…”

Section: Silacyclophanesmentioning

confidence: 99%

Molecular Structure of Sila-Heterocycles

Lukevics¹,

Pudova²

1998

Main Group Metal Chemistry

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The present review provides a comprehensive survey on the molecular structure of silaheterocyclic compounds (silacyclopropanes, silacyclobutanes, silacyclopentanes, silacyclohexanes and derivatives with larger rings, as well as compounds with fused and unsaturated heterocycles). In a lot of cases the heterocycles include also heteroatoms other than silicon, however, all silaheterocycles under consideration contain only Si-C bonds. INTRODUCTIONThe results of the structural investigations of the organosilicon heterocycles were reviewed in 1989 [1], However, sila-heterocycles have been the subject of extensive studies over the last 10 years. Much attention has been focused on the synthesis and structural characterization both derivatives with small rings and the macrocyclic compounds. There has been also a considerable interest in the cyclic π-electronic systems containing the silicon atom. Much of this interest concerns the possibility of aromatic character for the silole anions and dianions. Recently the first neutral silaaromatic compound -2-silanaphthalene was successfully isolated and structurally characterized. Our review is an attempt to summarize and systematize the numerous papers scattered in literature on this subject.

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Exoditopic receptors II: Synthesis and x-ray crystal structure of a disilamacrocycle bearing two bipyridine units

Cited by 34 publications

References 23 publications

Synthesis, Strain, Conformational Analysis, and Molecular and Crystal Structures of 1,1,4,4-Tetraphenyl-1,4-disilacyclohexane and 1,1,4,4-Tetraphenyl-1,4-disilacyclohexa-2,5-diene

Synthesis, Strain, Conformational Analysis, and Molecular and Crystal Structures of 1,1,4,4-Tetraphenyl-1,4-disilacyclohexane and 1,1,4,4-Tetraphenyl-1,4-disilacyclohexa-2,5-diene

Synthesis and structural studies on p-tert-butyl-1,3-dihydroxy-2,4-disulfanylcalix[4]arene and its mercury complex

Molecular Structure of Sila-Heterocycles

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