Synthesis and characterization of 3-thiophene carboxamides containing a pyridine ring: structure, electrochemistry, and complexation

Howell, S. Jarrett; Day, Cyn­thia S.; Noftle, Ronald E.

doi:10.1016/j.ica.2005.05.008

Cited by 13 publications

(16 citation statements)

References 40 publications

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“…The bound carbonyl group has a bond distance of 1.234(3) Å similar to that of 1.223(3) Å for the unbound carbonyl group in the other ligand. These values do not vary greatly from those for the free ligand [15] owing perhaps to donation of electron-density to the metal by the electron-rich, directly coordinating chloride ligands (2.3179(7), 2.3327(7) Å) which would decrease the metal-oxygen interaction. The metal center-donor atom bond distances are similar to those reported for other related Cu(II)-amide or amine structures [1,30,38,39].…”

Section: Synthesis and Characterizationmentioning

confidence: 79%

“…A chloride anion, which balances the overall 1+ charge on the complex, undergoes very weak hydrogen-bonding with the amide N-H group, the bound water molecule, and the lattice water molecule. The ligand C-O bond distance has increased to 1.257(2) Å over that of the free ligand, 1.235(4) Å [15]. The overall geometry of 9 is distorted square pyramidal with an O1-Cu-Cl1 angle of 161.49(4)° and an O2-Cu-N2 angle of 176.02(6)°.…”

Section: Synthesis and Characterizationmentioning

confidence: 97%

“…The metal environments in complexes 3 and 8 are distorted square pyramidal with a lone water molecule in the apical position. The C-O and amide bond distances in all three Zn(II) complexes change very little when compared with their respective free ligands [15], although complex 3 shows a more profound change in bond lengths [C-O bond: 1.257(7) Å, C-N bond: 1.326(5) Å for the chelated ligand versus 1.236(3) Å and 1.450(3) Å for the free ligand]. The bite angles for all three Zn(II) complexes are similar to the Cu(II) complexes with either perchlorate or hexafluorophosphate anions ranging from 91.73(6)° to 93.73(10)°.…”

Section: Synthesis and Characterizationmentioning

confidence: 98%

“…The compounds investigated by infrared spectroscopy, table 1, exhibit an NH stretching mode in the range of 3236-3375 cm −1 indicating that the amide nitrogen atom is not involved in coordination of the metal ion (data for 4 from a previous publication [15] are included for comparison). Compared to the free ligands, the amide I band is lowered about 40 cm −1 which is consistent with coordination by the carbonyl oxygen atom [16][17][18].…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…in an earlier paper [15] along with the preparation of a copper complex in which N-(2-pyridylmethyl)-3-thenyl-carboxamide acts as a bidentate ligand, 4.…”

Section: Introductionmentioning

confidence: 99%

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Metal complexes of 3-thiophene carboxamides containing a pyridine ring

Howell

Day

Noftle

2007

Inorganica Chimica Acta

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Complexes of Zn(II), Cu(II) and Co(II) with either N-(2-methylpyridyl)-3-thienyl-alkylcarboxamide or N-(2-pyridyl)-3-thienylalkyl-carboxamide groups have been prepared and characterized. Crystal structures of ten new complexes are reported and discussed. N-(2-Methylpyridyl)-3-thienyl-alkyl-carboxamide exhibits both uni-and bidentate behavior. With all ligands, bidentate complexation is through the carbonyl oxygen and pyridine nitrogen atoms (O, N) and the amide nitrogen atom remains protonated. The electrochemical behavior and the infrared spectra of selected complexes are discussed.

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Section: Synthesis and Characterizationmentioning

confidence: 79%

Section: Synthesis and Characterizationmentioning

confidence: 97%

Section: Synthesis and Characterizationmentioning

confidence: 98%

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…in an earlier paper [15] along with the preparation of a copper complex in which N-(2-pyridylmethyl)-3-thenyl-carboxamide acts as a bidentate ligand, 4.…”

Section: Introductionmentioning

confidence: 99%

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Metal complexes of 3-thiophene carboxamides containing a pyridine ring

Howell

Day

Noftle

2007

Inorganica Chimica Acta

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Metal‐containing Polymers via Electropolymerization

et al. 2011

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Electropolymerization represents a suitable and well-established approach for the assembly of polymer structures, in particular with regard to the formation of thin, insoluble films. Utilization of monomers that are functionalized with metal complex units allows the combination of structural and functional benefits of polymers and metal moieties. Since a broad range of both electropolymerizable monomers and metal complexes are available, various structures and, thus, applications are possible. Recent developments in the field of synthesis and potential applications of metal-functionalized polymers obtained via electropolymerization are presented, highlighting the significant advances in this field of research.

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Syntheses, Crystal Structures, and Physico‐Chemical Studies of Sodium and Potassium Alcoholates Bearing Thienyl Substituents and their Derived Luminescent Samarium(III) Alkoxides

Veith

Belot

Hüch

et al. 2010

Zeitschrift anorg allge chemie

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The synthesis, structural characterisation, electrochemistry, and luminescence properties of a series of alkali metal alcoholates and samarium(III) alkoxides with thiophene-based OR substituents are presented. The alkali metal alcoholates 7-15 were obtained by deprotonation of the carbinol with NaH or KH. Their molecular structures consist of tetranuclear alkali metal alcoholates with a distorted cubane-like M 4 O 4 core (Xray structure analyses). Each alkali metal is surrounded by three carbinolate ligands and (depending on the derivative) by additional tetrahydrofuran molecules. The mononuclear samarium alkoxides {Sm[OC(C 4 H 3 S) 3 ] 3 (thf) 3 }·thf (16) and {Sm[OC(C 16 H 13 S)] 3 (thf) 3 }·thf (17) were synthesised by the salt metathesis reactions between {[KOC(C 4 H 3 S) 3 ] 4 (thf) 2 }·thf (7), [NaOC(C 4 H 3 S) 3 ] 4 (thf) 2 (8) or * Prof. Dr. Dr. h. c. M. Veith E-Mail: Michael.Veith@inm-gmbh.de [a] www.zaac.wiley-vch.de 2263 [NaOC(C 4 H 3 S) 3 ] 4 (thf) 2 (8): All NaH had reacted. The solvent was evaporated; a solid was obtained, from which colorless crystals could be obtained in thf at 5°C. Yield 15 %, 243 mg. 1 H NMR (thf/C 6 D 6 ): δ = 6.9 (dd, 3 J H5-H4 = 4.9 Hz and 4 J H5-H3 = 1.2 Hz, 12H, 5-H), 6.8 (dd, 3 J H3-H4 = 3.4 Hz and 4 J H3-H5 = 1.2 Hz, 12H, 3-H), 6.7 (dd, 3 J H4-H3 = 3.7 Hz and 3 J H4-H5 = 4.9 Hz, 12H, 4-H). C 60 H 52 O 6 S 12 Na 4 : calcd. C 53.50; H 3.86 %; found C 52.24; H 3.56 %. [NaOC(C 14 H 11 S 2 )] 4 (thf) 2 (10): The unreacted NaH was filtered. The solvent was slowly evaporated, a light-brown solid precipitated, which was separated from the liquid residue. The isolated yield is 32 % (529 mg). 1 H NMR (thf/C 6 D 6 ): δ = 7.6 (dd, 3 J H5-H4 = 6.6 Hz and 4 J H5-H3 = 1.3 Hz, 8H, 5-H Th), 7.0 (m, 28 H, 4-H, Ph), 6.7 (dd, 3 J H4-H3 = 4.0 Hz, 8 H, 3-H Th). C 68 H 60 O 6 S 8 Na 4 : calcd. C 61.81; H 4.54 %; found C 60.61; H 4.39 %.[NaOC(C 17 H 15 S)] 4 (thf) 2 (13): The suspension turned into a solution.The solvent was slowly evaporated, a white solid precipitated, which

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Synthesis and characterization of 3-thiophene carboxamides containing a pyridine ring: structure, electrochemistry, and complexation

Cited by 13 publications

References 40 publications

Metal complexes of 3-thiophene carboxamides containing a pyridine ring

Metal complexes of 3-thiophene carboxamides containing a pyridine ring

Metal‐containing Polymers via Electropolymerization

Syntheses, Crystal Structures, and Physico‐Chemical Studies of Sodium and Potassium Alcoholates Bearing Thienyl Substituents and their Derived Luminescent Samarium(III) Alkoxides

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