Intramolecular N→Sn Coordination in Tin(II) and Tin(IV) Compounds Based on Enantiopure Ephedrine Derivatives

Zöller, Thomas; Iovkova‐Berends, Ljuba; Berends, Thorsten; Dietz, Christina; Bradtmöller, Gerrit; Jurkschat, Klaus

doi:10.1021/ic201203u

Cited by 35 publications

(16 citation statements)

References 35 publications

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“…The two Sn–O bond distances are close to being identical values. The calculated Sn–O bond distances of 2.0581/2.0644 Å in Bu 2 Sn(L 2 ) 2 are also close to the already reported Sn–O distances in {CH 2 N(Me)CH(Me)CH(Ph)O} 2 Sn (2.048/2.078) [ 49 ]. The two different Sn–N distances of Sn1–N5 and Sn1–N9 in compounds Bu 2 Sn(L 2 ) 2 are 2.1010/2.1050 Å, which are similar to the already reported structures, SalenH 2 Sn 2.0535(9) and 2.0369(8) Å) [ 50 ].…”

Section: Resultssupporting

confidence: 88%

Synthesis, Spectroscopic, Molecular Structure, and Antibacterial Studies of Dibutyltin(IV) Schiff Base Complexes Derived from Phenylalanine, Isoleucine, and Glycine

Singh

2014

Bioinorganic Chemistry and Applications

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New series of organotin(IV) complexes and Schiff bases derived from amino acids have been designed and synthesized from condensation of 1H-indole-2,3-dione, 5-chloro-1H-indole-2,3-dione, and α-amino acids (phenylalanine, isoleucine, and glycine). All compounds are characterized by elemental analyses, molar conductance measurements, and molecular weight determinations. Bonding of these complexes is discussed in terms of their UV-visible, infrared, and nuclear magnetic resonance (1H, 13C, and 119Sn NMR) spectral studies. The results suggest that Schiff bases behave as monobasic bidentate ligands and coordinate with dibutyltin(IV) in octahedral geometry according to the general formula [Bu2Sn(L)2]. Elemental analyses and NMR spectral data of the ligands with their dibutyltin(IV) complexes agree with their proposed distorted octahedral structures. Few representative compounds are tested for their in vitro antibacterial activity against Gram-positive (B. cereus, Staphylococcus spp.) and Gram-negative (E. coli, Klebsiella spp.) bacteria. The results show that the dibutyltin complexes are more reactive with respect to their corresponding Schiff base ligands.

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Section: Resultssupporting

confidence: 88%

Synthesis, Spectroscopic, Molecular Structure, and Antibacterial Studies of Dibutyltin(IV) Schiff Base Complexes Derived from Phenylalanine, Isoleucine, and Glycine

Singh

2014

Bioinorganic Chemistry and Applications

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“…As a result of the compression, the N → Sn distances in SnX 4 ·2py become shorter than the corresponding distances in SnX 2 ·2py. This agrees well with the experimental trend found on going from tetra‐coordinated Sn(II) to hexa‐coordinated Sn(IV) complexes . Both the SnX 2 · m py and SnX 4 · m py complexes manifest a clear dependence of d (N→Sn) on the kind of X.…”

Section: Resultssupporting

confidence: 86%

N → Sn coordination in the complexes of tin halides with pyridine: A comparison between Sn(II) and Sn(IV)

Matczak

2019

Applied Organom Chemis

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The experimentally well‐known complexation of tin(II) and tin(IV) halides with pyridine (py) leads to structures showing N → Sn coordination. In the present work, the complexes SnXn·mpy (where X = F, Cl, Br, I; n = 2, 4; m = 1, 2) possessing this kind of coordination were studied using a computational quantum chemical approach. Various aspects in the theoretical picture of these complexes were examined to find similarities and differences in their N → Sn coordination. The aspects included, among others, the physical nature of intermolecular interactions, and their role in establishing the structure and energetic stabilization of the complexes. In this context, the effect of tin valency was inspected in great detail. As proven by several theoretical methods, a largely ionic character with a certain covalent component can be attributed to the studied N → Sn coordination, irrespective of tin valency. All complexes are destabilized by py‐py and three‐body interactions, but the Sn(II) complexes experience it to a greater extent. Marked differences are observed in the structural behavior of N → Sn and SnXn during complex formation. This affects the energetics of complexation and, in consequence, the penta‐coordinated Sn(IV) center shows a higher propensity to expand its coordination number, compared with the tri‐coordinated Sn(II) center. The present study supplements the experimental characterization of SnXn·mpy and, in general, it sheds light on the coordination of heteroaromatic nitrogen to tin. The survey of the Cambridge Structural Database revealed that such coordination occurred in a number of crystal structures.

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“…Further, the shifting of the azomethine (−CH=N-) carbon signal in the spectra of the tin(II) compounds as compared to the free ligands, clearly indicates that the coordination through azomethine nitrogen to the tin atom. [29][30][31] which is below the reported values for tri-coordinated hydrated tin(II) chloride. Therefore, a fourcoordinate distorted tetrahedral geometry have been proposed for resulting tin(II) complexes (Fig.-2).…”

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confidence: 60%

Spectral, DFT and Antibacterial Studies of Tin(ii) Complexes of Schiff Bases Derived From Aromatic Aldehyde and Amino Acids

2017

Rasayan J Chem

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New tin(II) complexes of -amino acid Schiff bases (HL) derived from condensation of various -amino acids (tryptophan, phenylalanine, valine, isolecine, methionine, alanine, cysteine, serine, aspartic acid) and aromatic aldehyde were synthesized. The molar conductance low vales reveal that all the tin(II) complexes were nonelectrolytes. The structure of complexes were proposed in light of analytical techniques, infra-red, multinuclear magnetic resonance ( Sn), UV-Vis spectral data and theoretical studies. On the basis of these studies, complexes have distorted tetrahedral geometry. 3D structure of the newly synthesized compounds were studied by DFT/B3LYP method, also the theoretical parameters, HOMO, LUMO and dipole moments were calculated to confirm the geometry of the ligands and its tin(II) complexes. Few representative Schiff bases and its tin(II) complexes were screened for antibacterial activities. The tin(II) complexes have higher antibacterial activity than the free ligands.

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Intramolecular N→Sn Coordination in Tin(II) and Tin(IV) Compounds Based on Enantiopure Ephedrine Derivatives

Cited by 35 publications

References 35 publications

Synthesis, Spectroscopic, Molecular Structure, and Antibacterial Studies of Dibutyltin(IV) Schiff Base Complexes Derived from Phenylalanine, Isoleucine, and Glycine

Synthesis, Spectroscopic, Molecular Structure, and Antibacterial Studies of Dibutyltin(IV) Schiff Base Complexes Derived from Phenylalanine, Isoleucine, and Glycine

N → Sn coordination in the complexes of tin halides with pyridine: A comparison between Sn(II) and Sn(IV)

Spectral, DFT and Antibacterial Studies of Tin(ii) Complexes of Schiff Bases Derived From Aromatic Aldehyde and Amino Acids

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