The vilsmeier complex as a dehydrating agent in the synthesis of 2,6-dicyanopyridine

Gorbyleva, O. I.; Евстратова, М. И.; Yakhontov, L. N.

doi:10.1007/bf00505773

Cited by 4 publications

(6 citation statements)

References 1 publication

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“…4 and is very similar to the type 2 structures (though not isomorphous) except that one of the nitrate anions is monodentate with the Ho ؒ ؒ ؒ O(61) distance 3.76 Å. Monodentate nitrates are not common but as is apparent from the Cambridge Crystallographic Database have been observed before in a few lanthanide structures. This structure also shows hydrogen atoms on N(n1) as confirmed by a similar hydrogen bond pattern to type 2 in that N (11) is hydrogen bonded to a nitrate oxygen O(64) at 2.87(2) Å and N(31) to an acetonitrile nitrogen atom at 2.89(2) Å. The water molecule O(100) which is co-ordinated to the metal is also hydrogen bonded to O(64) and N(32) in two other molecules.…”

Section: Discussionsupporting

confidence: 66%

“…10 Its conversion into 2,6-dicyanopyridine was effected using a Vilsmeier complex as dehydrating agent. 11 The preparation of pyridine-2,6dicarbohydrazide imide was carried out by treating the cyanide with hydrazine hydrate in the absence of solvent. 12 The dicarbohydrazide imide was then converted into DBTZP as follows: 1 g (0.00518 mol) of it was initially suspended in DMF (20 cm 3 ) under a nitrogen atmosphere.…”

Section: Preparation Of Ligandsmentioning

confidence: 99%

“…Ellipsoids at 30% probability. † The structure of the corresponding erbium complex was found to be isomorphous but the data were not of sufficient quality to report: a = 16.123 (17), b = 8.211 (11), c = 16.625(14) Å, β = 101.69(1)Њ, monoclinic, space group P2 1 /n, Z = 4.…”

Section: Theoretical Structural Analysis Of Dmtzpmentioning

confidence: 99%

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Experimental and theoretical studies of a triazole ligand and complexes formed with the lanthanides

Drew¹,

Hudson²,

Iveson³

et al. 1999

J. Chem. Soc., Dalton Trans.

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Section: Discussionsupporting

confidence: 66%

Section: Preparation Of Ligandsmentioning

confidence: 99%

See 1 more Smart Citation

Experimental and theoretical studies of a triazole ligand and complexes formed with the lanthanides

Drew¹,

Hudson²,

Iveson³

et al. 1999

J. Chem. Soc., Dalton Trans.

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“…All starting materials were purchased from Aldrich except for pyridine-2,6-dicarbonitrile which was prepared as described previously. 23 Pyridine was dried over 4 Å molecular sieves before use. NMR spectra were run on a JEOL JNM-EX 400 spectrometer.…”

Section: Methodsmentioning

confidence: 99%

Solvent extraction and lanthanide complexation studies with new terdentate ligands containing two 1,3,5-triazine moieties

et al. 2004

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The extracting agent 2,6-bis(4,6-di-pivaloylamino-1,3,5-triazin-2-yl)-pyridine (L(5)) in n-octanol was found, in synergy with 2-bromodecanoic acid, to give D(Am)/D(Eu) separation factors (SFs) between 2.4 and 3.7 when used to extract the metal ions from 0.02-0.12 M HNO(3). Slightly higher SFs (4-6) were obtained in the absence of the synergist when the ligand was used to extract Am(III) and Eu(III) from 0.98 M HNO(3). In order to investigate the possible nature of the extracted species crystal structures of L(5) and the complex formed between Yb(III) with 2,6-bis(4,6-di-amino-1,3,5-triazin-2-yl)-pyridine (L(4)) were also determined. The structure of L(5) shows 3 methanol solvent molecules all of which form 2 or 3 hydrogen bonds with triazine nitrogen atoms, amide nitrogen or oxygen atoms, or pyridine nitrogen atoms. However, L(5) is relatively unstable in metal complexation reactions and loses amide groups to form the parent tetramine L(4). The crystal structure of Yb(L(4))(NO(3))(3) shows ytterbium in a 9-coordinate environment being bonded to three donor atoms of the ligand and three bidentate nitrate ions. The solvent extraction properties of L(4) and L(5) are far inferior to those found for the 2,6-bis-(1,2,4-triazin-3-yl)-pyridines (L(1)) which have SF values of ca. 140 and theoretical calculations have been made to compare the electronic properties of the ligands. The electronic charge distribution in L(4) and L(5) is similar to that found in other terdentate ligands such as terpyridine which have equally poor extraction properties and suggests that the unique properties of L(1) evolve from the presence of two adjacent nitrogen atoms in the triazine rings.

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“…Acetonitrile (Fisher HPLC grade) was purified by distillation from P 2 O 5 . Furan-2,5-dicarbonitrile and pyridine-2,6-dicarbonitrile were prepared according to literature methods. All reactions were carried out under an atmosphere of nitrogen.…”

Section: Methodsmentioning

confidence: 99%

Mixed Radical/Iodine Charge-Transfer Salts of Dithiadiazolyl Diradicals. Structural Characterization of the Pyridine-Bridged 2:1 Salt 2,6-[(S₂N₂C)C₅H₃N(CN₂S₂)]₂[I]

et al. 1996

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The vilsmeier complex as a dehydrating agent in the synthesis of 2,6-dicyanopyridine

Cited by 4 publications

References 1 publication

Experimental and theoretical studies of a triazole ligand and complexes formed with the lanthanides

Experimental and theoretical studies of a triazole ligand and complexes formed with the lanthanides

Solvent extraction and lanthanide complexation studies with new terdentate ligands containing two 1,3,5-triazine moieties

Mixed Radical/Iodine Charge-Transfer Salts of Dithiadiazolyl Diradicals. Structural Characterization of the Pyridine-Bridged 2:1 Salt 2,6-[(S₂N₂C)C₅H₃N(CN₂S₂)]₂[I]

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The vilsmeier complex as a dehydrating agent in the synthesis of 2,6-dicyanopyridine

Cited by 4 publications

References 1 publication

Experimental and theoretical studies of a triazole ligand and complexes formed with the lanthanides

Experimental and theoretical studies of a triazole ligand and complexes formed with the lanthanides

Solvent extraction and lanthanide complexation studies with new terdentate ligands containing two 1,3,5-triazine moieties

Mixed Radical/Iodine Charge-Transfer Salts of Dithiadiazolyl Diradicals. Structural Characterization of the Pyridine-Bridged 2:1 Salt 2,6-[(S2N2C)C5H3N(CN2S2)]2[I]

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Mixed Radical/Iodine Charge-Transfer Salts of Dithiadiazolyl Diradicals. Structural Characterization of the Pyridine-Bridged 2:1 Salt 2,6-[(S₂N₂C)C₅H₃N(CN₂S₂)]₂[I]