Potassium 3-cyano-4-(dicyanomethylene)-5-oxo-4,5-dihydro-1<i>H</i>-pyrrol-2-olate

Тафеенко, В. А.; Kaukova, Olga V.; Peschar, R.; Petrov, A. I.; Aslanov, L. A.

doi:10.1107/s0108270103020158

Cited by 10 publications

(6 citation statements)

References 8 publications

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“…We present here a novel and very ef®cient approach (94% yield) to the synthesis of 2-aminoethene-1,1,2-tricarbonitrile, (I). The crystallographic study of (I) extends our systematic investigation of the structural chemistry of enaminonitriles (Nasakin et al, 1991;Tafeenko et al, 1994a,b,c,d;Bogdan et al, 1996a,b) and molecules containing the dicyanoethylene fragment (Nasakin et al, 1992;Tafeenko et al, 2003Tafeenko et al, , 2005Tafeenko, Nikolaev et al, 2004;. Fig.…”

Section: Commentsupporting

confidence: 59%

The twofold interpenetrated three-connected three-dimensional (10,3)-net in 2-aminoethene-1,1,2-tricarbonitrile

et al. 2005

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In the crystal structure of the title compound, C5H2N4, each molecule is linked by N-H...N[triple-bond]C hydrogen bonds to four other molecules, thus forming a network that can be described as a twofold interpenetrated three-connected three-dimensional (10,3)-net. The interpenetrated nets are related by (010) translation. If only intermolecular hydrogen bonds are taken into account, these nets can be considered as independent. However, the interactions between the cyano groups from different nets indicate mutual assistance of the two nets during their formation.

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Section: Commentsupporting

confidence: 59%

The twofold interpenetrated three-connected three-dimensional (10,3)-net in 2-aminoethene-1,1,2-tricarbonitrile

et al. 2005

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“…The synthesis and structure of the potassium salt of the title anion have recently been reported for the ®rst time (Tafeenko et al, 2003). Organic salts containing this anion are of interest, from both a theoretical and an experimental point of view, because of their %±% interactions, which are due to the planarity of the organic moieties, and their tendency to form stacks.…”

Section: Commentmentioning

confidence: 99%

N-Methylpyridinium 3-cyano-4-(dicyanomethylene)-5-oxo-4,5-dihydro-1H-pyrrol-2-olate

Тафеенко

Nikolaev²,

Peschar³

et al. 2004

Acta Crystallogr C

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The crystal structure of the title compound, C(6)H(8)N(+).C(8)HN(4)O(2)(-), is characterized by three independent ion pairs (A, B and C) in the asymmetric unit. Each ion pair consists of an anion and a cation, and the three ion pairs have similar geometric parameters. All the anions are arranged as dianion dimers via two N-H.O hydrogen bonds and the dimers form one-dimensional columns parallel to the b axis as a result of pi-pi interactions. The cations are also stacked, in two different ways: one type of stacking consists of alternating A and B cations, while the other type consists of C cations only. Each dianion dimer stack is surrounded by eight stacks of cations and is not connected directly to other dianion stacks.

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“…title compound (I)] were prepared. The structure of the potassium salt, presented earlier (Tafeenko et al, 2003), possesses structural features that we expected would permit a systematic variation of the anion stacking distance. In the potassium salt, all exocyclic heteroatoms of A are involved in the formation of a nearly ideal tricapped trigonal prism that encloses the cation, and the anions are arranged in stacks as a result ofinteractions.…”

Section: Commentmentioning

confidence: 74%

Luminescence properties of three structures built from 3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrol-2-olate and alkaline metals (Na, K and Rb)

Тафеенко¹,

Gurskiy²,

Баранов³

et al. 2009

Acta Crystallogr C

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The structures of three salts of 3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrol-2-olate with alkali metals (Na, K and Rb) are related to their luminescence properties. The Rb salt, rubidium(I) 3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrol-2-olate, Rb(+).C(8)HN(4)O(2)(-), is isomorphous with the previously reported potassium salt. For the Na compound, sodium(I) 3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrol-2-olate dihydrate, Na(+).C(8)HN(4)O(2)(-).2H(2)O, two independent sodium ions, located on inversion centers, are coordinated by four water molecules each and additionally by two cyano groups for one and two carbonyl groups for the other. The luminescence spectra in solution are unaffected by the nature of the cation but vary strongly with the dielectric constant of the solvent. In the solid state, the emission maxima vary with structural features; the redshift of the maximum luminescence varies inversely with the distance between the stacked anions.

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Potassium 3-cyano-4-(dicyanomethylene)-5-oxo-4,5-dihydro-1H-pyrrol-2-olate

Cited by 10 publications

References 8 publications

The twofold interpenetrated three-connected three-dimensional (10,3)-net in 2-aminoethene-1,1,2-tricarbonitrile

The twofold interpenetrated three-connected three-dimensional (10,3)-net in 2-aminoethene-1,1,2-tricarbonitrile

N-Methylpyridinium 3-cyano-4-(dicyanomethylene)-5-oxo-4,5-dihydro-1H-pyrrol-2-olate

Luminescence properties of three structures built from 3-cyano-4-dicyanomethylene-5-oxo-4,5-dihydro-1H-pyrrol-2-olate and alkaline metals (Na, K and Rb)

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