TETRACYANOETHYLENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6N4
Molecular Weight	128.091
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N#CC(C#N)=C(C#N)C#N

InChI

InChIKey=NLDYACGHTUPAQU-UHFFFAOYSA-N

InChI=1S/C6N4/c7-1-5(2-8)6(3-9)4-10

HIDE SMILES / InChI

Molecular Formula	C6N4
Molecular Weight	128.091
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
TCNE-aniline charge transfer complex: ab initio and TDDFT investigations in gas phase.	2009-08	19172320
Acetylene-derived strong organic acceptors for planar and nonplanar push-pull chromophores.	2009-02-17	19061332
Tuning the electronic structure of graphene by an organic molecule.	2009-01-08	19072320
Tricyanovinylalkynyl-metal complexes: synthesis and some reactions.	2009-01-07	19081968
Charge-transfer complexations of 1,n-di(9-ethylcarbazol-3-yl)alkanes with tetracyanoethylene and tetranitromethane.	2009-01	18799351
High catalytic efficiency of nanostructured molybdenum trioxide in the benzylation of arenes and an investigation of the reaction mechanism.	2009	19035603
Synthesis, spectroscopic and thermal investigations of solid charge-transfer complexes of 1,4,7-trimethyl-1,4,7-triazacyclononane and the acceptors iodine, TCNE, TCNQ and chloranil.	2008-12-15	18691934
Strongly reshaped organic-metal interfaces: tetracyanoethylene on Cu(100).	2008-11-21	19113430
Supramolecular control of a fast and reversible Diels-Alder reaction.	2008-11-06	18847273
Click-type reaction of aromatic polyamines for improvement of thermal and optoelectronic properties.	2008-10-29	18834195
Meldrum's acid catalyzed reaction of tetracyanoethylene and aldehydes in water: a novel approach to arylidenemalononitrile.	2008-10	18827396
Spectroscopic investigation of the donor-acceptor interaction between o-phenylenediamine and tetracyanoethylene in dichloromethane.	2008-10	18054519
Mesoporous compound semiconductors from the reaction of metal ions with deltahedral [Ge9]4- clusters.	2008-08-27	18680285
Determination of the degree of charge-transfer contributions to surface-enhanced Raman spectroscopy.	2008-08-04	18613198
Pi-systems as simultaneous hydride and hydrogen bond acceptors.	2008-07-24	18593106
Synthesis, structure, and transannular pi-pi interaction of three- and four-layered [3.3]paracyclophanes.	2008-06-20	18498196
Spectrophotometric determination of terfenadine in pharmaceutical preparations by charge-transfer reactions.	2008-06-15	18585198
Reduced band gap dithieno[3,2-b:2',3'-d]pyrroles: new n-type organic materials via unexpected reactivity.	2008-04-17	18348567
Synthesis and magnetic properties of a [Ni(II)(TCNE)(NCMe)2-delta][BF4] magnet (Tc = 40 K).	2008-04-07	18321045
Solvent and spectral effects in the ultrafast charge recombination dynamics of excited donor-acceptor complexes.	2008-01-31	18181591
Single-molecule charge transfer and bonding at an organic/inorganic interface: tetracyanoethylene on noble metals.	2008-01	18069869
Spectrophotometric study of the charge transfer complexation of some porphyrin derivatives as electron donors with tetracyanoethylene.	2008-01	17493866
Synthesis, properties, and redox behavior of mono-, bis-, and tris[1,1,4,4,-tetracyano-2-(1-azulenyl)-3-butadienyl] chromophores binding with benzene and thiophene cores.	2008	18655087
One-electron-reduced and -oxidized stages of donor-substituted 1,1,4,4-tetracyanobuta-1,3-dienes of different molecular architectures.	2008	18642258
Antiaromaticity and reactivity of a planar cyclooctatetraene fully annelated with bicyclo[2.1.1]hexane units.	2008	18081128
Acetonitrile-facilitated reductive dimerization of TCNE to octacyanobutanediide, [C4(CN)8]2-, by Iron(II) chloride.	2008	17654625
New strong organic acceptors by cycloaddition of TCNE and TCNQ to donor-substituted cyanoalkynes.	2007-12-14	18361362
A re-evaluation of the electrophilic substitution reactions of the Ramirez ylide.	2007-11-09	17949041
Spectroscopic investigation of the charge-transfer interactions between 1,4,7-trimethyl-1,4,7-triazacyclononane and the acceptors iodine, TCNE, TCNQ and chloranil.	2007-11	17307029
Interaction of C-Si, C-Sn, and Si-Si sigma-bonds with chalcogen lone pairs.	2007-10-26	17915922
Tetranuclear complexes of [Fe(CO)2(C5H5)]+ with TCNX ligands (TCNX=TCNE, TCNQ, TCNB): intramolecular electron transfer alternatives in compounds (mu4-TCNX)[MLn]4.	2007-09-03	17691765
Spectroscopic studies of charge transfer complexes between colchicine and some pi acceptors.	2007-07	17029944
The first cyclopentadienylalkylphosphane nickel chelates: synthesis, structures, and reactions.	2007-06-04	17492707
Synthesis, structure, and transannular pi-pi interaction of multilayered [3.3]metacyclophanes.	2007-04-13	17355149
Synthesis, structure, and reactivity of mononuclear RE(I) oximato complexes.	2007-04-02	17298056
Four-center carbon-carbon bonding.	2007-03	17370990
Photosonochemical catalytic ring opening of alpha-epoxyketones.	2007-01-27	17257437
A diffusional alternative to the Marcus free energy gap law.	2007-01-21	17199156
Control of two-electron four-center (2e-/4c) C-C bond formation observed for tetracyanoethenide dimerization, [TCNE]2(2-).	2007-01-08	17198417
Using a tripod as a chiral chelating ligand: chemical exchange between equivalent molecular structures in palladium catalysis with 1,1,1-tris(oxazolinyl)ethane ("trisox").	2007	17525923
Magnetic ordering (Tc = 90 K) observed for layered [Fe(II)(TCNE*-)(NCMe)2]+[Fe(III)Cl4]- (TCNE = tetracyanoethylene).	2006-12-13	17147360
Iridium(III) silyl alkyl and iridacyclic compounds supported by 4,4'-di-tert-butyl-2,2'-bipyridyl.	2006-12-13	16991182
Charge transfer complex studies between some non-steroidal anti-inflammatory drugs and pi-electron acceptors.	2006-12	16716649
Synthesis of new 2-vinylation products of indole via a Michael-type addition reaction with dimethyl acetylenedicarboxylate and their Diels-Alder reactivity as precursors of new carbazoles.	2006-09-29	16995688
Optical, redox, and NLO properties of tricyanovinyl oligothiophenes: comparisons between symmetric and asymmetric substitution patterns.	2006-07-17	16628759
Solid-state NMR spectra and long intradimer bonds in the pi-[TCNE]22- dianion.	2006-06-29	16789786
Magnetically ordered molecule-based assemblies.	2006-06-21	16751881
Raman spectroscopy of short-lived terthiophene radical cations generated by photochemical and chemical oxidation.	2006-06-12	16673432
Effect of the excitation wavelength on the ultrafast charge recombination dynamics of donor-acceptor complexes in polar solvents.	2005-09-22	16834210
Increase in the mobility of photogenerated positive charge carriers in polythiophene.	2005-05-26	16852211

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:58:03 GMT 2025` Edited by `admin` on `Mon Mar 31 19:58:03 GMT 2025`
Record UNII	C592309ECU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRACYANOETHYLENE

Systematic Name

English

NSC-24833

Preferred Name

English

TETRACYANOETHYLENE [MI]

Common Name

English

Code System Code Type Description

FDA UNII

C592309ECU