Methyl substituted benzene adducts of trimeric perfluoro-o-phenylene mercury

Haneline, Mason R.; King, Julie B.; Gabbaı̈, François P.

doi:10.1039/b304023b

Cited by 37 publications

(37 citation statements)

References 51 publications

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“…18.6 %), occurring at 150–200 °C. This compares well with the trend for [{Hg‐ o ‐(C 6 F 4 )} 3 (arene)] complexes where mass loss began at below 50 °C for the PhMe and 1,2‐ or 1,3‐Me 2 C 6 H 4 derivatives, but at 91 °C for the 1,3,5‐Me 3 C 6 H 3 complex 5c. The solid‐state 13 C CPMAS NMR resonances of the aromatic carbon atoms of TMB in [HgR 2 (TMB)] (R = C 6 F 4 ‐ m ‐NO 2 , C 6 F 5 ) were only slightly deshielded (ca.…”

Section: Resultssupporting

confidence: 86%

The Supramolecular Architecture of Arene Complexes of Bis(polyfluorophenyl)mercurials

et al. 2008

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The 1:1 (arene)mercury complexes [HgR2(arene)] [R = C6F4‐o‐NO2, C6F4‐m‐NO2, C6F4‐o‐H, C6F5; arene = TMB (1,2,4,5‐tetramethylbenzene), PMB (1,2,3,4,5‐pentamethylbenzene)] are readily formed when mixtures of the mercurial and arene are crystallised from CH2Cl2 or CH2Cl2/hexane. Analogous 1:1 complexes are also formed from Hg(C6F5)2 and PhMe, whereas novel 1:2 complexes [HgR2(arene)2] result from Hg(C6F4‐o‐NO2)2 and PhMe or TMO (1,2,4‐trimethoxybenzene) and from Hg(C6F5)2 and TMO. In the crystalline state, the 1:1 [HgR2(arene)] complexes exist as canted columns of alternating planar HgR2 and arene layers linked by weak (Hg···C 3.2–3.5 Å) η1 or η2 π‐arene–mercury interactions. For the TMB (R = C6F4‐o‐NO2, C6F4‐o‐H, C6F5) and PhMe (R = C6F5) complexes, the packing of neighbouring columns shows aligned, alternating fluoroarene and arene ring planes resulting in a 2D brick‐wall motif with potential supramolecular components (fluoroarene–fluoroarene and fluoroarene–arene stacking). For the TMB complex with R = C6F4‐m‐NO2 the 2D array is distorted into a herringbone motif by weak C–H···O interactions. The 1:2 complex [Hg(C6F4‐o‐NO2)2(PhMe)2] has an analogous mercury environment to the 1:1 complexes, and the packing shows a distinct layer structure of alternating rows of PhMe and HgR2 with two PhMe units per HgR2 unit but with no inter‐stack interactions. The TMO complexes have long Hg···O contacts (3.2 Å) rather than Hg···C and similarly show a layered structure, but in this case, with a single column of alternating HgR2 and pairs of TMO. Theoretical calculations for the 1:2 [HgR2(TMB)2] complexes (R = C6F4‐o‐NO2, C6F4‐m‐NO2) are consistent with the findings from the observed crystal structures. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Section: Resultssupporting

confidence: 86%

The Supramolecular Architecture of Arene Complexes of Bis(polyfluorophenyl)mercurials

et al. 2008

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“…The complex occupies in the crystal a special position on an inversion centre and represents a doubledecker sandwich. The PCP ligand in 2 is disposed between the mutually parallel planes of the two mercuramacrocycles and it coordinates to them by its benzene rings through secondary p- [21]). The shortest HgeC arene contact (3.052 A) in the series of arene complexes of macrocycle 1 was observed in the structure of the 1:1 adduct of 1 with nonplanar indenocorannulene [18].…”

Section: Resultsmentioning

confidence: 99%

Coordination chemistry of mercury-containing anticrowns. Synthesis and structure of an unusual discrete, double-decker sandwich complex of cyclic trimeric perfluoro-o-phenylenemercury with an aromatic hydrocarbon

Tikhonova

Gribanyov

Tugashov

et al. 2010

Journal of Organometallic Chemistry

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“…By contrast, [Hg(thioacetanilide) 2 ] in the solid state is quite unsymmetrical, having a coordination interaction (also 3 ) for only one of the two ligands (shortest Hg Á Á Á C ¼ 2.963-3.275 Å ), while the other is oriented well away from mercury [15], and [HgL 2 ] in which L is a ligand with methoxy attached to the [13] finds about 20 examples of structures in which a mercury lies in an approximately perpendicular line above a benzene ring with at least one Hg Á Á Á C distance 5 3.1 Å (about 60 if the search is extended to 3.2 Å ), in many of which this arrangement is not imposed by intramolecular bonding constraints. In crystallographic studies, secondary interactions of mercury with aromatic rings have been investigated by NMR spectroscopy, magnetic measurements, and luminescence properties [17][18][19][20][21][22], and they appear to be weak but significant.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and crystal structures of bis(N-phenyl-3,5-dinitrothiobenzamidato)mercury(II) and bis(N-phenyl-4-nitrothiobenzamidato)mercury(II)

Habibi

Tangestaninejad

Fallah-Shojaei

et al. 2010

Journal of Coordination Chemistry

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The crystal structures of bis(N-phenyl-3,5-dinitrothiobenzamidato)mercury(II) (1) and bis(N-phenyl-4-nitrothiobenzamidato)mercury(II) (2) have been determined by single-crystal X-ray diffraction. Both the complexes crystallize in centrosymmetric monoclinic space groups with crystallographic inversion symmetry. The S-Hg-S linkage is thus precisely linear in each case. Significant secondary interactions include intramolecular coordination by phenyl groups, aromatic ring stacking in the case of 1 only, and a number of intramolecular and intermolecular C-H Á Á Á X contacts (X ¼ O, N, S) influencing the molecular conformation and crystal packing.

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Methyl substituted benzene adducts of trimeric perfluoro-o-phenylene mercury

Cited by 37 publications

References 51 publications

The Supramolecular Architecture of Arene Complexes of Bis(polyfluorophenyl)mercurials

The Supramolecular Architecture of Arene Complexes of Bis(polyfluorophenyl)mercurials

Coordination chemistry of mercury-containing anticrowns. Synthesis and structure of an unusual discrete, double-decker sandwich complex of cyclic trimeric perfluoro-o-phenylenemercury with an aromatic hydrocarbon

Synthesis and crystal structures of bis(N-phenyl-3,5-dinitrothiobenzamidato)mercury(II) and bis(N-phenyl-4-nitrothiobenzamidato)mercury(II)

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