Synthesis, crystal structures and spectroscopic properties of dichloroethylphenyltin(IV) and its phenanthroline adduct

Casas, José S.; Castellano, Eduardo E.; Ellena, Javier; García‐Tasende, María S.; Sánchez, Agustı́n; Sordo, José; Taboada, Cristina; Vidarte, María J.

doi:10.1002/aoc.552

Cited by 10 publications

(4 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The results can be assigned to the similar effects of DMSO and phen on the NMR parameters. Notably, similar results have also been found in the case of NMR parameters of [SnEtPhCl 2 (phen)] in DMSO‐ d 6 …”

Section: Resultssupporting

confidence: 84%

Exploiting the versatility of pyridyl ligands for the preparation of diorganotin (IV) adducts: spectral, crystallographic and Hirshfeld surface analysis studies

Momeni

Fathi

Abbasi

et al. 2019

Applied Organom Chemis

View full text Add to dashboard Cite

Diorganotin (IV) complexes SnR 2 X 2 (R = Me, Ph; X = Cl, NCS) form a series of versatile complexes when react with bidentate substituted pyridyl ligands. The reaction of dimethyltin dichloride with 5,5′-dimethyl-2,2′-bipyridine (5,5′-Me 2 bpy) resulted in the formation of [SnMe 2 Cl 2 (5,5′-Me 2 bpy)] (1). Moreover, the reaction of SnMe 2 (NSC) 2 with 4,4′-di-tert-butyl-2,2′-bipyridine (bu 2 bpy), 1,10-phenanthroline (phen) and 4,7-diphenyl-1,10-phenanthroline (bphen) affords the hexa-coordinated complexes [SnMe 2 (NCS) 2 (bu 2 bpy)] (2), [SnMe 2 (NCS) 2 (phen)] (3) and [SnMe 2 (NCS) 2 (bphen)] (4), respectively. The resulting complexes have been characterized using elemental analysis, IR, multinuclear NMR ( 1 H, 13 C, 119 Sn) and DEPT-135°NMR spectroscopy. On the other hand, the reaction of diphenyltin dichloride with 2,2′-biquinoline (biq) and 4,7-phenantroline (4,7-phen) led to the formation of polymeric complexes of [SnPh 2 Cl 2 (4,7-phen)] n (5) and [SnPh 2 Cl 2 (biq)] n (6). The NMR spectra, however, reveal the ligand lability in solution and suggest a coordination number of 5. The X-ray crystal structures of complexes [SnMe 2 Cl 2 (5,5′-Me 2 bpy)] (1), [SnMe 2 (NCS) 2 (bu 2 bpy)] (2) and [SnMe 2 (NCS) 2 (bphen)] (4) have been determined which reveal that the geometry around the tin atom is distorted octahedral with trans-[SnMe 2 ] configuration. Interestingly, the crystal structure of (H 2 biq) 2 [SnPh 2 Cl 4 ]•2CHCl 3 (7) was characterized by X-ray crystallography from a chloroform solution of [SnPh 2 Cl 2 (biq)] n (6) indicating the formation of doubly protonated [H 2 biq] + and [Ph 2 SnCl 4 ] 2− which are stabilized by a network of hydrogen bonds with a feature of trans-[SnPh 2 ]. The 3D Hirshfeld surface analysis and 2D fingerprint maps were used for quantitative mapping out of the intermolecular interactions for 1, 2, 4 and 7 which show the presence of π-π and hydrogen bonding interactions which are associated between donor and acceptor atoms (N, S, Cl) in the solid state.

show abstract

Section: Resultssupporting

confidence: 84%

Exploiting the versatility of pyridyl ligands for the preparation of diorganotin (IV) adducts: spectral, crystallographic and Hirshfeld surface analysis studies

Momeni

Fathi

Abbasi

et al. 2019

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…The above data suggest that either the interaction of [SnMe 2 Cl 2 ] with 4,7‐phen is not maintained in solution and the complex undergoes partial dissociation in DMSO, 4,7‐phen being replaced by DMSO, or 4,7‐phen and DMSO have similar effects on the NMR parameters. The latter is very possible and such an observation has already been reported …”

Section: Resultsmentioning

confidence: 54%

“…One of the most impressive bidentate ligands is 1,10‐phenanthroline and its derivatives such as 4,7‐diphenyl‐1,10‐phenanthroline, 1,10‐phenanthroline‐5,6‐dione, dipyridophenazine, 5‐X‐1,10‐phenanthroline (X = Me, NO 2 , Cl) and 5,6‐dimethyl‐1,10‐phenanthroline. A variety of hexa‐coordinated tin (IV) complexes have been synthesized by the reaction of [SnR 2 X 2 ] (R = Me, Et, n Bu, Ph; X = Cl, NCS) with chelating 1,10‐phenanthroline ligand and its derivatives …”

Section: Introductionmentioning

confidence: 99%

Structure–reactivity studies of chloro and isothiocyanato diorganotin (IV) complexes based on multidentate N‐donor ligands: Synthesis, spectral characterization and crystal structures

Momeni

Sefidabi

Khademi

et al. 2018

Applied Organom Chemis

View full text Add to dashboard Cite

The reaction of [SnMe2Cl2] with the bidentate ligand 4,7‐phenanthroline (4,7‐phen) resulted in the formation of [SnMe2Cl2 (4,7‐phen)]n (1a) which is probably a polymeric chain in solution. On the other hand, the reaction of [SnEt2Cl2] with 4,7‐phen afforded the complex [Sn2Et4Cl4 (κ1‐N‐4,7‐phen)2(μ‐κ2‐N,N‐4,7‐phen)] (1b) which dissociates in dimethylsulfoxide solution. The reaction of [SnR2Cl2] (R = Me, Et) with 2,2′‐biquinoline (biq) yielded the complexes [SnMe2Cl2 (κ2‐N,N‐biq)] (2a) and [SnEt2Cl2 (κ1‐N‐biq)2] (2b) in the solid state. Moreover, the reaction of [SnR2Cl2] (R = Me, Et) with the tridentate ligand 4′‐(2‐furyl)‐2,2′:6′,2″‐terpyridine (ftpy) resulted in the formation of ionic penta‐ and hexa‐coordinated tin complexes [SnMe2Cl (ftpy)][SnMe2Cl3] (3a) and [SnEt2Cl (ftpy)]Cl (3b). The reaction of [SnMe2 (NCS)2] with ftpy afforded the hepta‐coordinated complex [SnMe2 (NCS)2(ftpy)] (4a). The products were fully characterized using elemental analysis, and infrared, UV–visible, multinuclear (1H, 13C, 119Sn) NMR, DEPT‐135°, HH‐COSY and HSQC NMR spectroscopies. The crystal structure of complex 3a reveals that it contains the simultaneous presence of penta‐ and hexa‐coordinated tin (IV) atoms. Notably, the crystal structure of complex 4a shows that tin (IV) is hepta‐coordinated in a pentagonal bipyramidal geometry SnC2N5 by three nitrogen atoms of ftpy, two nitrogen atoms of NCS− and two Me groups with trans‐[SnMe2] configuration. These data indicate the influence of halide or pseudo‐halide group on the coordination number and geometry of tin. Hirshfeld surface analysis and two‐dimensional fingerprint plots were calculated for 3a and 4a which show the π–π interaction between molecules in the solid is relatively weak.

show abstract

“…1) ;Alcock & Sawyer, 1977) as type P. The less symmetrical members of both structure-type families can be further classified according to the symmetry elements responsible for the chain propagation. Other structure types based on an infinite polymeric association pattern can be classified as einer-double chains or bands (-Cy 2 SnCl 2 ; Ganis et al, 1986), zweier-single chains (Ph 2 SnCl 2 ; Greene & Bryan, 1971) or sheets (EtPhSnCl 2 ; Casas et al, 2003).…”

Section: Commentmentioning

confidence: 99%

Dibromodiphenylstannane: isolated centrosymmetric dimers as a new structure motif for the intermolecular association of diorganotin(IV) dihalides

Reuter

2012

Acta Crystallogr C

View full text Add to dashboard Cite

In the crystalline state, the low-melting title compound [common name: diphenyltin(IV) dibromide], [SnBr(2)(C(6)H(5))(2)], consists of distorted tetrahedral molecules with compressed halide and enlarged carbon opening angles of 102.741 (9) and 123.53 (8)°, respectively, and Sn-C and Sn-Br bond lengths of 2.109 (2)/2.113 (2) and 2.4710 (3)/2.4947 (3) Å, respectively. Intermolecular Sn...Br interactions, typical for diorganotin(IV) dihalides, R(2)SnHal(2) (with Hal = Cl, Br, I), and sterically less demanding organic groups lead to the formation of a hitherto unknown association pattern consisting of centrosymmetric dimers with an antiparallel orientation of the dipole moments and two weak intermolecular Sn...Br distances of 3.8482 (3) Å between one of the two Br atoms and its neighbouring Sn atom, and vice versa. The second Br atom is not involved in intermolecular interactions and lies somewhat outside the association plane that, therefore, is not coplanar [interplanar angle = 1.750 (2)°] with the tin-halide plane. The new structure motif of intermolecular tin-halide interaction can be classified as 2a(i), which indicates the number of molecules (i.e. '2') composing the oligomer, the antiparallel orientation (i.e. 'a') of their dipole moments and the centre of symmetry (i.e. 'i') giving rise to the association pattern.

show abstract

Synthesis, crystal structures and spectroscopic properties of dichloroethylphenyltin(IV) and its phenanthroline adduct

Cited by 10 publications

References 19 publications

Exploiting the versatility of pyridyl ligands for the preparation of diorganotin (IV) adducts: spectral, crystallographic and Hirshfeld surface analysis studies

Exploiting the versatility of pyridyl ligands for the preparation of diorganotin (IV) adducts: spectral, crystallographic and Hirshfeld surface analysis studies

Structure–reactivity studies of chloro and isothiocyanato diorganotin (IV) complexes based on multidentate N‐donor ligands: Synthesis, spectral characterization and crystal structures

Dibromodiphenylstannane: isolated centrosymmetric dimers as a new structure motif for the intermolecular association of diorganotin(IV) dihalides

Contact Info

Product

Resources

About