Tri-n-butyltin 2,6-Difluorobenzoate, a Unique Macrocyclic Tetramer Containing a 16-Membered Sn4C4O8 Ring, and Other Related Compounds

Gielen, Marcel; Elkhoulfi, A.; Biesemans, Monique; Kayser, François; Willem, Rudolph; Mahieu, Bernard; Maes, Dominique; Lisgarten, J.N.; Wyns, Lode; Moreira, Ariele C.; Chattopadhay, Tk.; Palmer, R. A.

doi:10.1021/om00019a047

Cited by 54 publications

(27 citation statements)

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“…31 -33 However, there are two R 3 Sn(O 2 CR ) structures in the literature that adopt the tetrameric motif reported here for 5. 34,35 The rationalization of the appearance of these cyclotetrameric structures, which may be thought of as being intermediate between the monomeric and polymeric extremes described above, remains elusive.…”

Section: 21mentioning

confidence: 99%

Di‐ and tri‐organotin(IV) derivatives of (Z)‐3‐(4‐nitrophenyl)‐2‐phenyl‐2‐propenoic acid: spectroscopic characterization and biocidal studies. Crystal structure analysis of tetrameric tri‐n‐butyltin(IV) (Z)‐3‐(4‐nitrophenyl)‐2‐phenyl‐2‐propenoate

Sadiq‐ur‐Rehman

Ali

Badshah

et al. 2004

Applied Organom Chemis

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Seven new organotin(IV) compounds containing the carboxylate ligand (Z)-3-(4-nitrophenyl)-2-phenyl-2-propenoate (L) have been synthesized with formulations of R 2 SnL 2 (R = Me, Et, n-Bu, n-Oct) and R 3 SnL, (R = Me, n-Bu, Ph). All compounds have been studied in solution by multinuclear ( 1 H, 13 C, 119 Sn) magnetic resonance spectroscopy. The solid-state structures have been investigated by means of FT-IR spectroscopy and the molecular structure of one example, namely n-Bu 3 SnL, has been determined by X-ray crystallography. The novel structure of n-Bu 3 SnL is tetrameric owing to the presence of bidentate bridging carboxylate ligands. The solution studies show collapse of the intermolecular interactions observed in the solid state to yield monomeric species. Some of the new compounds were found to display significant biocidal activities.

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Section: 21mentioning

confidence: 99%

Di‐ and tri‐organotin(IV) derivatives of (Z)‐3‐(4‐nitrophenyl)‐2‐phenyl‐2‐propenoic acid: spectroscopic characterization and biocidal studies. Crystal structure analysis of tetrameric tri‐n‐butyltin(IV) (Z)‐3‐(4‐nitrophenyl)‐2‐phenyl‐2‐propenoate

Sadiq‐ur‐Rehman

Ali

Badshah

et al. 2004

Applied Organom Chemis

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“…The axial angle of 171.19(10)° for the Sn1 atom is more significantly distorted from the ideal angle compared with Sn2 atom, for which the equivalent angle is 177.62(11)°. There are three R 3 Sn(O 2 CR`) structures reported in the literature[27][28][29] that adopt tetrameric motif. The rationalization of the appearance of…”

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confidence: 99%

Structural chemistry of organotin(IV) complexes

Shahzadi

Ali

2008

JICS

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The amazing structural diversity in organotin compounds is discussed in the systems containing -O and -S donor ligands. It is demonstrated that there exist a fascinating range of structural diversity for organotin(IV) complexes, including differences in coordination number and molecular geometry. The difference in structure is correlated with the nature of tin and ligand bonded R groups. Despite the large number of different structures found in organotin(IV) carboxylates, there is limited range of coordination geometries about the Sn atom. The four coordinated Sn atom in triorganotin(IV) complexes is invariably distorted tetrahedral and five coordinated Sn is distorted trigonal bipyramidal. A large range has been observed for diorganotin carboxylate structures, where five, six and seven coordinate geometries have been reported. The Sn atom in mono-organotin has only been demonstrated to exist in distorted octahedral geometries (the single exception being a pentagonal bipyramidal geometry). In the case of organotin(IV) complexes of S donor ligands, it has been shown that there exists a rich diversity in Sn atom geometries and coordination modes of the sulfur donor ligands themselves. As in related carboxylate systems, the assignment of coordination numbers to the Sn centers in some compounds is controversial. As a general trend, it has been shown that, the overall coordination number at the Sn atom decreases with the increasing number of organic substituents at the Sn atom. This phenomenon is usually achieved by increased asymmetry in the mode of coordination of the sulfur donor ligands.

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“…This value elevates to 117 Hz for trichloroacetate derivatives in DMSO, which shows further extension of the tin coordination number. In fact, similar to other triorganotin acetates [17], polymeric solid state structures of diphenylmethyltin acetates in solution depolymerize to their monomers as a four-coordinated species and then coordination of solvent returns it to the fiveor six-coordinated status. The 2 J ( 119 Sn C 1 H) value also slightly increases with increasing chlorine substitution on the acetate group, a trend which is similar to that found for trimethyltin chloroacetates and opposite to that of dimethyltin chloride chloroacetates [16].…”

Section: Resultsmentioning

confidence: 81%

Synthesis and characterization of diphenylmethyltin(IV) mono‐, di‐, and trichloroacetate

Amini

Yousefi

2003

Heteroatom Chemistry

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Tri-n-butyltin 2,6-Difluorobenzoate, a Unique Macrocyclic Tetramer Containing a 16-Membered Sn4C4O8 Ring, and Other Related Compounds

Cited by 54 publications

References 0 publications

Di‐ and tri‐organotin(IV) derivatives of (Z)‐3‐(4‐nitrophenyl)‐2‐phenyl‐2‐propenoic acid: spectroscopic characterization and biocidal studies. Crystal structure analysis of tetrameric tri‐n‐butyltin(IV) (Z)‐3‐(4‐nitrophenyl)‐2‐phenyl‐2‐propenoate

Di‐ and tri‐organotin(IV) derivatives of (Z)‐3‐(4‐nitrophenyl)‐2‐phenyl‐2‐propenoic acid: spectroscopic characterization and biocidal studies. Crystal structure analysis of tetrameric tri‐n‐butyltin(IV) (Z)‐3‐(4‐nitrophenyl)‐2‐phenyl‐2‐propenoate

Structural chemistry of organotin(IV) complexes

Synthesis and characterization of diphenylmethyltin(IV) mono‐, di‐, and trichloroacetate

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