Packing studies in cyano-aromatic compounds: the structure of 1,4-benzenedicarbonitrile

Drück, U.; Littke, W.

doi:10.1107/s056774087801016x

Cited by 25 publications

(11 citation statements)

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“…The C---CN distance of 1.430 (7). ,~, is comparable to C---CN distances of 1.451 (13)A in the 1,4-isomer (Driick & Littke, 1978), 1.446(8)/~ in 1,2,4,5-tetracyanobenzene (Prout & Tickle, 1978) and 1.439 (6)/~ in 4-cyanopyridine (Laing, Sparrow & Sommerville, 1971). This bond length is intermediate between the expected value of 1.419 A for sp-sp 2 C--C bond lengths and the value of 1.459 A for sp---sp 3 C---C bond lengths (Stoecheff, 1962).…”

mentioning

confidence: 61%

“…The two cyano groups are slightly bent above the benzene plane retaining molecular symmetry m. This plane is perpendicular to the benzene ring and bisects the C(1)---C(1 ~) and C(3)--C(3 i) bonds [symmetry code: (i) -x, y, z]. The mean aromatic C---C bond length of 1.377/~ is comparable to analo~gous mean distances found in the 1,4-isomer (1.388A; Driick & Littke, 1978) and in 1,2,4,5-tetracyanobenzene [1.401 (8)/~; Prout & Tickle, 1978]. The ~N bond length of 1.149 (8)/~ is typical of cyano groups and comparable to C--N distances found in various cyano derivatives (Britton, 1981a, b;Casado, Nygaard & Sorensen, 1971;Colapietro, Domenicano, Marciante & Portalone, 1981).…”

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confidence: 84%

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1,2-Dicyanobenzene. A Precursor of Phthalocyanines

Janczak¹,

Kubiak²

1995

Acta Crystallogr C

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confidence: 61%

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confidence: 84%

1,2-Dicyanobenzene. A Precursor of Phthalocyanines

Janczak¹,

Kubiak²

1995

Acta Crystallogr C

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“…The1 ,4-dicyanobenzene (DCB) molecule,w hich has ac alculated dipole moment of zero,i so ne of the simplest derivatives of benzene,d isubstituted with cyano groups at para positions,t hus resulting in D 2h point group symmetry (Figure 2a). DCB is commonly used as araw material for the synthesis of various chemicals,i ncluding medicines and agrochemicals.S ingle crystals of DCB,w hich belong to the triclinic P " 1s pace group [39] and melt at 221-225 8 8C, are afforded by recrystallization from an acetone solution.…”

Section: Shape Rememorization Of An Organosuperelastic Crystal Througmentioning

confidence: 99%

Shape Rememorization of an Organosuperelastic Crystal through Superelasticity–Ferroelasticity Interconversion

et al. 2019

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As altering permanent shapes without loss of material function is of practical importance for material molding, especially for elastic materials,s hape-rememorization ability would enhance the utility of elastic crystalline materials.Since diffusionless plastic deformability can preserve the crystallinity of materials,t he interconversion of diffusionless mechanical deformability between superelasticity and ferroelasticity could enable shape rememorization of superelastic single crystals.T his study demonstrates the shape rememorization of an organosuperelastic single crystal of 1,4-dicyanobenzene through time-reversible interconversion of superelasticity-ferroelasticity relaxation by holding the mechanically twinned crystal without heating. The shaperememorization ability of the organosuperelastic crystal indicates the compatibility of superelasticity (antiferroelasticity) and ferroelasticity as well as the intrinsic workability of organic crystalline materials capable of recovering their crystal functions under mild conditions. Practical applications of solid materials demand not only appropriate functions but also appropriate shapes.S ome polycrystalline and amorphous materials,s uch as alloys and polymers,are available in various shapes through molding in ad iffusion manner by thermal processes,i nw hich thermal stability is essential. On the other hand, reshaping singlecrystalline materials,i nw hich at hree-dimensional order is kept, is achieved by ac ombination of cutting,f iling, [1] and etching [2,3] according to their physical and chemical characteristics and intended use.R ecently,t he mechanical deformability of organic crystals has attracted great attention. Among their properties,s uperelasticity (SE) [18,[28][29][30][31] and ferroelasticity (FE) [19][20][21][22][23][24][25][26] give crystallographically well-regulated deformability while retaining single crystallinity. SE and FE have been developed in the fields of the materials science of metal alloys and the physics of ferroics, [32] respectively.M echanical deformations through both SE and FE are realized by diffusionless plastic deformability, whereby SE spontaneously recovers from strain and FE leaves permanent strain. In so-called shape-memory alloys (SMAs), [33][34][35] the shape is recovered because of the thermal generation of SE by as olid-state phase transition based on Gibbs free energy gaps,t hat is,m artensitic SE (mSE). Therefore,twinning deformation irrelevant to phase changes basically leads to twinning FE (tFE). Although tFE was claimed in an organic crystal of squaric acid in 1979, [19] tFE has now been identified in an increasing number of organic crystals and become commonplace in organic crystals composed of structurally flexible molecules. [19][20][21][22][23][24][25][26] Furthermore, multiple tFE effects with versatile deformability have been found in a1 ,4-diethoxybenzene crystal. [26] Tw inning deformability is apotential effective reshaping procedure for organic single crystals.Some organic crystals exhibit SE, so-called...

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“…A secondary interest was to see whether the two compounds were in fact isomorphous, since in a number of cases aromatic nitriles are not isomorphous with the corresponding isonitrile. As examples, 2,4,6-tribromobenzonitrile (Carter and Britton, 1972) packs differently from the isonitrile (Carter and Britton, 1977), and terephthalonitrile (van Rij and Britton, 1977;Druck and Littke, 1978;Colapietro et al, 1984a) packs differently from p-diisocyanobenzene (Hulme, 1952;Colapietro et al, 1984b).…”

Section: Introductionmentioning

confidence: 96%

Crystal structure of p-isocyanoaniline

Britton

1993

Journal of Crystallographic and Spectroscopic Research

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Packing studies in cyano-aromatic compounds: the structure of 1,4-benzenedicarbonitrile

Cited by 25 publications

References 3 publications

1,2-Dicyanobenzene. A Precursor of Phthalocyanines

1,2-Dicyanobenzene. A Precursor of Phthalocyanines

Shape Rememorization of an Organosuperelastic Crystal through Superelasticity–Ferroelasticity Interconversion

Crystal structure of p-isocyanoaniline

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