Heptacoordinated diphenyllead; hexa- and pentacoordinated triphenyllead and tin compounds derived from 5H-benzimidazo[1,2-c]quinazoline-6-thione

Esparza‐Ruiz, Adriana; Peña-Hueso, Adrián; Ramos-Garcı́a, Iris; Flores‐Parra, Angelina; Contreras, Rosalinda

doi:10.1016/j.jorganchem.2008.05.022

Cited by 13 publications

(9 citation statements)

References 32 publications

(35 reference statements)

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“…[55] Interestingly, the large upfield shifts in the 119 Sn NMR spectra were observed in DMSO-d 6 (À 467.3 ppm for TAz-H, À 471.1 ppm for TAz-F, À 465.0 ppm for TAz-OBu and À 475.9 ppm for TAz-CF3, Figure S2), strongly suggesting that the DMSO coordination should proceed at the tin atom followed by the formation of the six coordinated state. [56][57][58][59] This result also means that the asymmetric five-and six-coordinated structures can be obtained by selecting the solvent between CDCl 3 and DMSO-d 6 , respectively. Noted that the complexes involving six-coordinated states showed high stability.…”

Section: Nmr Spectramentioning

confidence: 83%

Vapochromic Luminescent π‐Conjugated Systems with Reversible Coordination‐Number Control of Hypervalent Tin(IV)‐Fused Azobenzene Complexes

Gon

Tanaka

Chujo

2021

Chemistry A European J

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The dynamic and reversible changes of coordination numbers between five and six in solution and solid states, based on hypervalent tin(IV)-fused azobenzene (TAz) complexes, are reported. It was found that the TAz complexes showed deep-red emission owing to the hypervalent bond composed of an electron-donating three-center four-electron (3c-4e) bond and an electron-accepting nitrogen-tin (N-Sn) coordination. Furthermore, hypsochromic shifts in optical spectra were observed in Lewis basic solvents because of alteration of the coordination number from five to six. In particular, vapochromic luminescence was induced by attachment of dimethyl sulfoxide (DMSO) vapor to the coordination point at the tin atom accompanied with a crystal-crystal phase transition. Additionally, the color-change mechanism and degree of binding constants were well explained by theoretical calculation. To the best of our knowledge, this is the first example of vapochromic luminescence by using stable and variable coordination numbers of hypervalent bonds.

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Section: Nmr Spectramentioning

confidence: 83%

Vapochromic Luminescent π‐Conjugated Systems with Reversible Coordination‐Number Control of Hypervalent Tin(IV)‐Fused Azobenzene Complexes

Gon

Tanaka

Chujo

2021

Chemistry A European J

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“…In complex 6 the Sn1‐N3 bond distance, although long, is in the range of other compounds found in the literature, so the ligand coordinates to the metal in a bidentate manner, giving rise to the formation of a four‐member chelate ring, coordination mode that has been previously observed in related complexes . The metal is in a C 3 NS coordination environment (Figure ) with a value of the τ 5 parameter of 0.68, corresponding to a strongly distorted trigonal bipyramid environment (τ 5 = 0 for square‐pyramid and τ 5 = 1 for trigonal bipyramid) .…”

Section: Resultsmentioning

confidence: 65%

Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives

Huedo

Zani

Mendiola

et al. 2018

Applied Organom Chemis

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Six organotin (IV) complexes with two ligands derived from 2,3‐butanedione and thiosemicarbazide have been synthesized and fully characterized by several spectroscopic techniques, including 119Sn NMR and single crystal X‐ray diffraction. Reactions of the ligand diacetyl‐2‐(thiosemicarbazone)‐3‐(3‐hydroxy‐2‐naphthohydrazone), L1H2, with SnR2Cl2 (R = Me, Bu, Ph) lead to the obtaining of complexes 1–3 with general formula [SnR2L1] (R = Me 1, R = Bu 2, R = Ph 3), in which the ligand is doubly deprotonated and behaves as a N2SO donor, whereas from the reactions of diacetyl‐2‐thiosemicarbazone, HATs, with the same organotin precursors any complex could be isolated. By contrast, reaction of HATs with SnR3Cl induces the ligand cyclization to form a 1,2,4‐triazine‐3‐thione that binds to the metal as a monoanionic donor in a mono or bidentate manner to form compounds 4–6 with formula [SnR3L2] (R = Me 4, R = Bu 5, R = Ph 6). The antimicrobial activity of the ligands and the six complexes was tested towards bacteria and fungi, including clinical isolated strains. The results show that the ligands are devoid of activity, except HATs that displays activity against Bacillus subtilis. Conversely, the complexes exhibit good antimicrobial properties against Gram positive and negative bacteria, yeasts and moulds. The best results are obtained for complexes [SnBu3L2] 5 and [SnPh3L2] 6, indicating that their more lipophilic nature could play an important role in the ease of microbial cell penetration. In some cases, these complexes display similar or higher activity than that of ampicillin and miconazole, used as antibacterial and antifungal positive controls, respectively. Docking study with DHPS protein (S. aureus) has shown that out of six drugs, the compound 6 has the best binding affinity (−8.5 Kcal/mol).

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“…Crystals of 5, 6 and 8 were obtained from THF, 7 from a CDCl 3 -DMSO-d 6 mixture and 4 from DMSO-d 6 . In the asymmetric unit of 5 and 8 there was also THF molecules non-coordinated to tin.…”

Section: Crystallographic Studymentioning

confidence: 99%

“…We are currently investigating the chemistry of organotin compounds derived from polyfunctional planar aromatic ligands, such as diphenolamines [1], diphenoloxamides [2][3][4] and thiolamines derived from benzimidazole [5,6]. The rigid framework of the aromatic ligands allows the synthesis of hypervalent tin compounds having diverse structures and inter-and intramolecular weak interactions.…”

Section: Introductionmentioning

confidence: 99%

Hypervalent triphenyl and diphenyl tin coordination compounds derived from 2-(1H-benzimidazol-2-yl)phenol

Esparza‐Ruiz

Peña-Hueso

Ramos-Garcı́a

et al. 2009

Journal of Organometallic Chemistry

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Heptacoordinated diphenyllead; hexa- and pentacoordinated triphenyllead and tin compounds derived from 5H-benzimidazo[1,2-c]quinazoline-6-thione

Cited by 13 publications

References 32 publications

Vapochromic Luminescent π‐Conjugated Systems with Reversible Coordination‐Number Control of Hypervalent Tin(IV)‐Fused Azobenzene Complexes

Vapochromic Luminescent π‐Conjugated Systems with Reversible Coordination‐Number Control of Hypervalent Tin(IV)‐Fused Azobenzene Complexes

Synthesis, antimicrobial activity and molecular docking of di‐ and triorganotin (IV) complexes with thiosemicarbazide derivatives

Hypervalent triphenyl and diphenyl tin coordination compounds derived from 2-(1H-benzimidazol-2-yl)phenol

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