The Crystal Structure of Sodium Tricyanomethanide, NaC(CN)3.

Andersen, Per Thomas; Klewe, Bernt; Thom, Erling; Stoll, E.; Eriksson, G.; Blinc, R.; Paušak, S.; Ehrenberg, L.; Dumanović, J.

doi:10.3891/acta.chem.scand.21-1530

Cited by 62 publications

(14 citation statements)

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“…Thevariety of small distortions from mm2 symmetry shows that the geometry of this anion is measurably sensitive to its environment. This phenomenon has already been observed in the C(CN)s ion, which shows different deviations from planarity in the ammonium, sodium, and potassium salts (Desiderato & Sass, 1965;Andersen, Klewe & Thorn, 1967;Andersen, 1967;Witt & Brittod, 1971), in the C(CN) (NO2)~-ion, which shows different C-NO2 torsion angles in the rubidium ~ind potassium salts (Bjornstad & Klewe, 1972;, and in the C(NO2)~" ion, which shows different C-NO2 torsion angles in the crystallographically discrete ions in the hydrazinium salt and in the potassium salt (Dickens, 1970;Golovina & Atovmyan, 1967). Klewe (private communication) has determined the structure of KC(CN)2NO2.…”

Section: Resultsmentioning

confidence: 68%

The structure of silver dicyanonitromethanide, AgC(CN)₂NO₂

Chow¹,

Britton²

1974

Acta Crystallogr Sect B

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Silver dicyanonitromethanide, AgC(CN)2NO2, is monoclinic, space group C2/c with a = 29.571 (20), b = 7.818 (8), c = 19.581 (14) Å, β=116.69 (5)°, Z = 32, Dcalc = 2.863 g cm−3, Dobs = 2.87 (5) g cm−3. Least‐squares refinement of diffractometer data converged at a conventional R index of 0.035. The four crystallographically independent C(CN)2NO2− ions are all close to planar and close to mm2 symmetry but with real deviations from both. The average bond lengths are: C‐C, 1.389 (6); C‐N, 1.373 (8); C N, 1.140 (6); N‐O, 1.252 (6) Å. Seven of the eight cyano groups are coordinated more or less linearly to silver ions at N … Ag distances of 2.12 to 2.34 Å. Each of the four nitro groups acts as a bidentate ligand to a single silver ion with O … Ag distances from 2.28 to 3.00 Å. There are also several other N … Ag and O … Ag distances under 3.00 Å. The coordination about each of the silver ions is highly irregular.

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Section: Resultsmentioning

confidence: 68%

The structure of silver dicyanonitromethanide, AgC(CN)₂NO₂

Chow¹,

Britton²

1974

Acta Crystallogr Sect B

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“…The dimensions of the tricyanomethanide anion found here (CÀC 1.401-1.402 ; CÀN 1.148-1.150 ) are more reliable than those found in the earlier crystal structure analyses. [6][7][8] Note that the hydrogen bonds are all directed towards the N atoms of the tricyanomethanide anion and not towards the central C atom with its formal negative charge.…”

Section: Resultsmentioning

confidence: 99%

“…Indeed, we have obtained a crystalline hydrate with properties similar to but not identical with those described earlier by others, [1][2][3] but it has turned out, however, to be hydronium tricyanomethanide (3) with planar tricyanomethanide anions identical with those observed previously in other crystalline tricyanomethanide salts. [4][5][6][7][8] Only in the gas phase at a pressure of less than 40 mTorr has tricyanomethane been identified by Bak and Svanhout from its microwave spectrum. [9] History The tricyanomethane story begins in 1896 when Schmidtmann added dilute sulfuric acid to an aqueous solution of sodium tricyanomethanide.…”

Section: Introductionmentioning

confidence: 99%

The Search for Tricyanomethane (Cyanoform)

Šišak

McCusker

Buckl

et al. 2010

Chemistry A European J

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Although listed in organic chemistry textbooks as one of the strongest carbon acids, and in spite of more than a hundred years of attempts to prepare the compound, tricyanomethane (cyanoform) has resisted isolation and characterization, either as the carbon-acid 1 or as the dicyanoketenimine tautomer 2. Only in the vapor phase at very low pressure has the compound been identified from its microwave spectrum. Here we review and partially repeat the preparative work. With the aid of spectroscopic and diffraction methods (including powder diffraction) we have identified some of the products obtained as: hydronium tricyanomethanide (3), (Z)-3-amino-2-cyano-3-iminoacrylimide (4), a co-crystal of 4 with sulfuric acid (or corresponding iminium salt), and an addition product of 2 with hydrochloric acid (5/6). Quantum-mechanical calculations at the MP2/6-311++g(2d,2p) level have been made to assess the relative energies of some of the molecules involved.

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“…Dieses hat die in Abbildung 1 wiedergegebene Moleku È lstruktur, in der das Natrium-Atom tetraedrisch von dem Iod-Atom und von den N-Atomen der drei Phosphanimin-Moleku È le koordiniert ist. Zur Einscha È tzung der den langen Abstand bedingenden kurzen Na±N-Bindungen in 1 seien die Na±N-Absta È nde in Vergleichsverbindungen genannt: In dem Aminoimino-Phosphoronat-Komplex [Na(THF) 6 ] + -[Na{(NSiMe 3 ) 2 PPh 2 } 2 ] ± [10] liegen sie bei gleicher Koordinationszahl wie in 1 zwischen 238, 9 und 242,4 pm,in [NaI(pmdeta)] 2 [9] zwischen 246,9 und 254,1 pm, und im Natrium-tricyano-methanid, NaC(CN) 3 [11] mit oktaedrischer N 6 -Koordination zwischen 237,1 und 261,3 pm. u.)…”

Section: [Nai(hnpph 3 ) 3 ]´05 Thf (1´05 Thf)unclassified

Die Kristallstrukturen der Phosphanimin-Komplexe [NaI(HNPPh3)3] und [SrI2(HNPPh3)2(THF)2] sowie des Natrium-triphenylphosphaniminats [NaNPPh3]6

Gröb

Müller

Massa

et al. 2001

Z. anorg. allg. Chem.

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Professor Hans-Georg von Schnering zum 70. Geburtstag gewidmet Inhaltsu È bersicht. [NaI(HNPPh 3 ) 3 ] (1) entsteht als gelbe, feuchtigkeitsempfindliche Kristalle als Zwischenverbindung bei der Synthese von Natrium-triphenylphosphaniminat, [NaNPPh 3 ] 6 (2), aus Ph 3 PI 2 und Natriumamid in flu È ssigem Ammoniak. Entsprechend entstehen farblose Kristalle von [SrI 2 (HNPPh 3 ) 2 (THF) 2 ] (3) aus Strontiumamid und Ph 3 PI 2 in flu È ssigem Ammoniak und anschlieûender Kristallisation des prima È r gebildeten [SrI 2 (HNPPh 3 ) 4 ] aus Tetrahydrofuran. Die Komplexe 1±3 werden hauptsa È chlich durch Kristallstrukturanalysen charakterisiert.1´0,5 THF: Raumgruppe P3c1, Z = 4, Gitterkonstanten bei 193 K: a = b = 1533,2(1); c = 2545,6(1) pm, R = 0,0417. 1 hat eine Moleku È lstruktur, in der das Natriumatom tetraedrisch von einem Iod-Atom im Abstand von 315,9 pm und von den N-Atomen der drei HNPPh 3 -Moleku È le im Abstand von 238,9 pm umgeben ist. 2´C 7 H 8 : Raumgruppe P1, Z = 1, Gitterkonstanten bei 213 K: a = 1457,1(1), b = 1484,9(1), c = 1502,7(1) pm; a = 116,32(1)°, b = 115,358(10)°, c = 93,585(14)°; R = 0,0520. 2 hat eine Moleku È lstruktur, in der die sechs Natriumatome und die sechs Stickstoff-Atome der (NPPh 3 ± )-Gruppen ein hexagonales Prisma mit angena È herter D 3d -Symmetrie bilden. 3´2 THF: Raumgruppe P1, Z = 2, Gitterkonstanten bei 193 K: a = 1042,9(1), b = 1337,4(1), c = 2095,1(1) pm; a = 90,130(8)°, b = 96,310(8)°, c = 111,985(8)°; R = 0,0310. 3 hat eine Moleku È lstruktur, in der das Strontium-Atom oktaedrisch von den einander paarweise gegenu È berstehenden Iod-Atomen, von den N-Atomen der Phosphanimin-Moleku È le und von den Sauerstoff-Atomen der Tetrahydrofuran-Moleku È le koordiniert ist. Crystal Structures of the Phosphaneimine Complexes [NaI(HNPPh 3 ) 3 ] and [SrI 2 (HNPPh 3 ) 2 (THF) 2 ], as well as of Sodium Triphenylphosphoraneiminate [NaNPPh 3 ] 6Abstract. [NaI(HNPPh 3 ) 3 ] (1) has been obtained as yellow, moisture sensitive crystals as an intermediate product of the synthesis of sodium triphenylphosphoraneiminate, [NaNPPh 3 ] 6 (2) from Ph 3 PI 2 and sodium amide in liquid ammonia.Correspondingly, colourless crystals of [SrI 2 (HNPPh 3 ) 2 (THF) 2 ] (3) are formed from strontium amide and Ph 3 PI 2 in liquid ammonia and subsequent recrystallisation of the primary product [SrI 2 (HNPPh 3 ) 4 ] from thf solution. The complexes 1±3 are mainly characterized by crystal structure determinations.1´0,5 thf: space group P3c1, Z = 4, lattice dimensions at 193 K: a = b = 1533.2(1); c = 2545.6(1) pm, R = 0.0417. 1 has a molecular structure in which the sodium atom is tetrahedrally coordinated by the iodine atom with a distance of 315.9 pm and by the nitrogen atoms of the three HNPPh 3 molecules with a distance of 238.9 pm.2´C 7 H 8 : space group P1, Z = 1, lattice dimensions at 213 K: a = 1457.1(1), b = 1484.9(1), c = 1502.7(1) pm; a = 116.32(1)°, b = 115.358(10)°, c = 93.585(14)°; R = 0.0520. 2 has a molecular structure in which the six sodium atoms and the six nitrogen atoms of the (NPPh 3 ± ) groups ...

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The Crystal Structure of Sodium Tricyanomethanide, NaC(CN)3.

Cited by 62 publications

References 0 publications

The structure of silver dicyanonitromethanide, AgC(CN)₂NO₂

The structure of silver dicyanonitromethanide, AgC(CN)₂NO₂

The Search for Tricyanomethane (Cyanoform)

Die Kristallstrukturen der Phosphanimin-Komplexe [NaI(HNPPh3)3] und [SrI2(HNPPh3)2(THF)2] sowie des Natrium-triphenylphosphaniminats [NaNPPh3]6

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The Crystal Structure of Sodium Tricyanomethanide, NaC(CN)3.

Cited by 62 publications

References 0 publications

The structure of silver dicyanonitromethanide, AgC(CN)2NO2

The structure of silver dicyanonitromethanide, AgC(CN)2NO2

The Search for Tricyanomethane (Cyanoform)

Die Kristallstrukturen der Phosphanimin-Komplexe [NaI(HNPPh3)3] und [SrI2(HNPPh3)2(THF)2] sowie des Natrium-triphenylphosphaniminats [NaNPPh3]6

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The structure of silver dicyanonitromethanide, AgC(CN)₂NO₂

The structure of silver dicyanonitromethanide, AgC(CN)₂NO₂