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Cas Database

74-90-8

74-90-8

Identification

  • Product Name:Hydrocyanic acid

  • CAS Number: 74-90-8

  • EINECS:200-821-6

  • Molecular Weight:27.0256

  • Molecular Formula: CHN

  • HS Code:2811.19

  • Mol File:74-90-8.mol

Synonyms:Acide cyanhydrique;BRN 1718793;Carbon hydride nitride (CHN);Acido cianidrico;Formic anammonide;Formonitrile;Hydrogen cyanide;Prussic acid;Cyclon;UN 1051;UNII-2WTB3V159F;

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Safety information and MSDS view more

  • Pictogram(s):HighlyF+,VeryT+,DangerousN

  • Hazard Codes:F+,T+,N

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Half-upright position. No mouth-to-mouth artificial respiration. Administration of oxygen may be needed. Refer for medical attention. See Notes. In case of skin contact Rinse skin with plenty of water or shower. Refer for medical attention . Wear protective gloves when administering first aid. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. NO mouth-to-mouth artificial respiration. Administration of oxygen may be needed. Refer for medical attention . See Notes. Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)Excerpt from ERG Guide 117 [Gases - Toxic - Flammable (Extreme Hazard)]: TOXIC; Extremely Hazardous. May be fatal if inhaled or absorbed through skin. Initial odor may be irritating or foul and may deaden your sense of smell. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control may cause pollution. (ERG, 2016)It is super toxic. Breathing in a small amount of the gas or swallowing a very small amount may be fatal. Average fatal dose is 50-60 mg. A few minutes of exposure to 300 ppm may result in death. Exposure to 150 ppm for 1/2 to 1 hour may endanger life. (EPA, 1998)Excerpt from ERG Guide 117 [Gases - Toxic - Flammable (Extreme Hazard)]: TOXIC; Extremely Hazardous. May be fatal if inhaled or absorbed through skin. Initial odor may be irritating or foul and may deaden your sense of smell. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control may cause pollution. (ERG, 2016)Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016) /PREHOSPITAL/ Management of cyanide poisoning begins with removal to fresh air. Dermal decontamination is unnecessary if exposure has been only to vapor, but wet clothing should be removed and the underlying skin should be washed with soap and water or water alone if liquid on the skin is a possibility. Attention to the basics of intensive supportive care is critical and includes mechanical ventilation as needed, circulatory support with crystalloids and vasopressors, correction of metabolic acidosis with IV sodium bicarbonate, and seizure control with benzodiazepine administration. ... Administration of 100% oxygen has been found empirically to exert a beneficial effect and should be a part of general supportive care for every cyanide-poisoned patient. /Cyanides/

  • Fire-fighting measures: Suitable extinguishing media Fire situation may require evacuation. Allow burning of material until flow of gas can be stopped. Use water spray, dry chemical, "alcohol resistant" foam, or carbon dioxide. Water may be ineffective. Approach fire from upwind. Fight fire from protected location or maximum possible distance. Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)Excerpt from ERG Guide 117 [Gases - Toxic - Flammable (Extreme Hazard)]: These materials are extremely flammable. May form explosive mixtures with air. May be ignited by heat, sparks or flames. Vapors from liquefied gas are initially heavier than air and spread along ground. Vapors may travel to source of ignition and flash back. Runoff may create fire or explosion hazard. Cylinders exposed to fire may vent and release toxic and flammable gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket. (ERG, 2016)Unstabilized hydrocyanic acid may polymerize spontaneously with explosive violence. Flashback along vapor trail may occur. The explosion hazard is severe when this material is exposed to heat, flame, or oxidizers. It forms explosive mixtures with air, and will react with water, steam, acid, or acid fumes to produce highly toxic fumes of cyanides. It may decompose explosively upon contact with alkaline material. Avoid acetylaldehyde, alkaline materials, oxidizers, water, steam, acid, and acid fumes. Hydrocyanic acid solution is sensitive to light. It may become unstable and subject to explosion if stored for an extended time or exposed to high temperature and pressure. Avoid heat, flame or oxidizers. Hazardous polymerization may occur. Unstabilized hydrocyanic acid may polymerize spontaneously with explosive violence. Can polymerize at 122-140F or when catalyzed with traces of alkali. (EPA, 1998)Excerpt from ERG Guide 117 [Gases - Toxic - Flammable (Extreme Hazard)]: These materials are extremely flammable. May form explosive mixtures with air. May be ignited by heat, sparks or flames. Vapors from liquefied gas are initially heavier than air and spread along ground. Vapors may travel to source of ignition and flash back. Runoff may create fire or explosion hazard. Cylinders exposed to fire may vent and release toxic and flammable gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket. (ERG, 2016)Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Evacuate danger area! Consult an expert! Personal protection: gas-tight chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Ventilation. Remove all ignition sources. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. NEVER direct water jet on liquid. 1. Remove all ignition sources. 2. Ventilate area of spill or leak. 3. If in gaseous form, stop flow of gas. If source of leak is cylinder & leak cannot be stopped in place, remove ... to safe place in open air ... repair leak or allow cylinder to empty.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from food and feedstuffs. Cool. Store only if stabilized.Keep cylinders of hydrogen cyanide (HCN) cool and away from open flames. Make certain that HCN cylinders are adequately supported and grounded during storage and emptying. Store cylinders in a vertical position. Do not drop cylinders or damage them by impact. Cylinders must be returned to the supplier within 90 days of the filling date marked on the cylinders, regardless of whether or not the contents have been used. This is due to the possibility of HCN becoming unstable over time. If there is any indication that the HCN is becoming unstable, such as a darkening of the product or an increase in cylinder pressure, contact the supplier immediately for instructions.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 15 Min Short-Term Exposure Limit: 4.7 ppm (5 mg/cu m). Skin.Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 294 Articles be found

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Howard,Hilbert

, p. 1918,1921, 1922 (1938)

-

Anderson, H. H.

, p. 1757 - 1759 (1942)

Observation of high vibrational excitation in HCN molecules produced from 193 nm photolysis of 1,3,5-triazine

Goates, S. R.,Chu, J. O.,Flynn, G. W.

, p. 4521 - 4525 (1984)

Infrared emission from the ν2 bending mode and ν3 C-H stretching mode of HCN have been observed following 193 nm pulsed excimer laser photolysis of 1,3,5-triazine.Using a simple harmonic oscillator analysis, the number of ν2 bending quanta produced in HCN from photolysis of sym-triazine was found to be 70 times larger than the number of ν3 C-H stretching quanta.The combination of a high density of bending vibrational states in HCN and favorable geometry changes which occur in going from 1,3,5-triazine to three HCN molecules, appear to give an unusually pure distribution which maximizes vibrational energy in the HCN bending mode.

On self-limitation of UV photolysis in rare-gas solids and some of its consequences for matrix studies

Khriachtchev, Leonid,Pettersson, Mika,Raesaenen, Markku

, p. 727 - 733 (1998)

UV photolysis of small molecules embedded in rare-gas matrices is examined. We demonstrate that photolysis can be self-limited when products absorb the photolysing radiation. As a result of the rising absorption, in-situ detected luminescence of the photolysis product saturates faster than its concentration. In particular, the present study supports the conclusion that 193 nm photolysis of hydrogen-containing species in Xe matrices produces hydrogen atoms in amounts comparable with the other dissociating part of the precursor. Also, we show that 193 nm radiation activates mobility of hydrogen atoms in annealing, accelerating photochemical processes related to hydrogen mobility.

Andrussow

, (1938)

Mechanism of Ni removal from Si materials using hydrogen cyanide aqueous solutions

Liu, Yueh-Ling,Takahashi, Masao,Kobayashi, Hikaru

, p. H16-H19 (2007)

The mechanism of Ni removal from Si O2 -covered Si specimens by HCN aqueous solutions has been investigated by means of total reflection X-ray fluorescence spectroscopy and X-ray photoelectron spectroscopy measurements. Ni contaminants on the Si O2 surface are present in the form of SiO-NiOH. The removal mechanism consists of two steps, i.e., an initial fast process followed by a slow process. The rate-determining steps of both the processes are of the first order with respect to the concentration of cyanide ions (C N-). The fast and slow processes are tentatively attributed to the removal of SiO-NiOH on terraces and in sub-nanometer pores, respectively. The cleaning ability of the HCN aqueous solutions is much better than ammonia aqueous solutions, because of high reactivity to form nickel-cyanide complex ions and avoidance of readsorption of Ni (CN) 4 2- complex ions in the solutions.

King, C. M.,Nixon, E. R.

, p. 1685 - 1695 (1968)

Matrix Infrared Spectra of the NH3--HCN and NH3--(HCN)2 Complexes in Solid Argon

Bohn, Robert B.,Andrews, Lester

, p. 3974 - 3979 (1989)

The NH3--HCN complex has been observed and characterized in an argon matrix.It is a strongly bonded complex with C3v geometry.New absorptions attributable to perturbed vibrations in each submolecule have been observed, especially a new red-shifted absorption νc3(CH) for the perturbed C-H stretching fundamental with blue-shifted absorptions assigned to νc1(CN), νc2(HCN), and νc2(NH3).A low-frequency absorption assigned to the librational motion of HCN in the complex was also observed and agrees well with calculated results.Comparison with the gas-phase spectrum shows that the matrix interaction stabilizes the complex.Spectra for the higher order 1:2 NH3--(HCN)2 complexes are presented, assigned, and compared to NH3--HCN and (HCN)2.

Multicomponent reaction of conjugated enynones with malononitrile and sodium alkoxides: Complex reaction mechanism of the formation of pyridine derivatives

Kuznetcova, Anastasiya V.,Odin, Ivan S.,Golovanov, Alexander A.,Grigorev, Iakov M.,Vasilyev, Aleksander V.

, p. 4516 - 4530 (2019)

Reaction of conjugated enynones,1,5-diarylpent-2-en-4-yn-1-ones, with malononitrile and sodium alkoxides in the corresponding alcohols at room temperature for 3–23 h results in the formation of two types of compounds (E)-/(Z)-6-aryl-4-(2-arylethenyl)-2-alkoxypyridine-3-carbonitriles (substituted nicotinonitriles), as the major reaction products in yields up to ca. 40–80%, and 6-aryl-4-arylethynyl-2-alkoxypyridines, as the minor reaction products in yields of 5–17%. Plausible mechanism of this complex and multistep reaction is discussed. The obtained pyridines possess fluorescent properties.

Infrared spectra of (HCN)(n) clusters in low-temperature argon matrices

Satoshi, Kudoh,Takayanagi, Masao,Nakata, Munetaka

, p. 365 - 369 (1997)

The infrared spectra of the HCN monomer, linear (HCN)2 and cyclic (HCN)3 were measured using a low-temperature matrix isolation technique. Linear (HCN)2 and cyclic (HCN)3 were produced by the photolysis of s-tetrazine and s-triazine respectively. Vibrational analyses of the infrared bands for the C-H stretching, the C-N stretching and H-C-N bending modes were performed with the aid of ab initio calculations; geometrical optimization was carried out using the density functional theory (DFT) method with a 6-31++G** basis set.

Yates,Heider

, p. 4153 (1952)

Franchetti et al.

, p. 5926 (1975)

Investigations of Small Carbon Cluster Ion Structures by Reactions with HCN

Parent, Denise C.,McElvany, Stephen W.

, p. 2393 - 2401 (1989)

The results of a detailed study of the primary and secondary reactions of carbon cluster ions, Cn(1+) (3=20), with HCN are used as a probe of the structures of small carbon cluster ions.The experiments were performed in a Fourier transform ICR mass spectrometer (FTMS), using direct laser vaporization of graphite to form the carbon cluster ions.The only ionic products observed for the HCN reactions were CnX(1+) (primary reaction product) and CnXY(1+) (secondary reaction product) where X and Y = H, CN, or HCN.Radiative association is an important reaction channel.Products resulting from fragmentation of the reactant carbon cluster ion were not observed.Evidence for two structural forms of the n = 7-9 cluster ions is presented.The anomalous behavior of C7(1+) is interpreted by an isomerization mechanism.Low-energy collision-induced dissociation studies of the primary product ions support a mechanism of carbene insertion into the H-CN bond and formation of covalently bonded products.In contrast, the HCN associates weakly with most primary product ions.

Vibrational stark effects of nitriles I. Methods and experimental results

Andrews, Steven S.,Boxer, Steven G.

, p. 11853 - 11863 (2000)

The C-N stretch mode of several small nitriles was analyzed by measuring vibrational Stark effects. Conjugated and unconjugated nitriles as well as mono- and dinitriles were immobilized in frozen 2-methyl-tetrahydrofuran glass and examined in externally applied electric fields using FTIR. Room temperature absorption spectra of several nitriles (butyronitrile, hydrogen cyanide, valeronitrile, and deuterated aceonitrile) showed no concentration dependent effects between 2.4 mM and 0.8 M. Difference dipole moments, Δμ, equivalent to the linear Stark tuning rate, were 0.01/f-0.04/f Debye (0.2/f-0.7/f/cm(/MV/cm)) for most samples, with aromatic compounds toward the high end and symmetric dinitriles toward the low end. Most quadratic Stark effects were small and negative, while transition polarizabilities were positive and had a significant effect on Stark line shapes. For aromatic nitriles, transition dipoles and Δμ values agreed with Hammett numbers. Symmetric dinitrile Δμ values decreased monotonically with increasing conjugation of the connecting bridge, likely due to improved mechanical coupling and, to a lesser extent, an increased population of inversion symmetric conformations. Δμ values were close to those expected from bond anharmonicity and ab initio predictions.

Analysis of products from a C2H2/N2 microwave discharge: New nitrile species

Fujii, Toshihiro

, p. 733 - 740 (1999)

The production of gaseous hydrocarbons, nitriles, amines, and hydrazines in a continuous-flow microwave plasma discharge excited in a 20% C2H2+80% N2 mixture at a pressure of 20 Torr is reported. The product analysis was made by Li+ ion attachment mass spectrometry. A variety of N-containing organics (identified as HCnN (n=1-7), NC(CC)nCN (n=0-2), NC(CH2)nCN (n=0-6), CnH2n-1NH2 (n=0-6), CnH2n+1N(H)NH2 (n=0-5), etc.) were formed and these were tentatively assigned to nitriles, amines, and hydrazines. The mass-spectral analysis exhibited progressions differing by 14 mass units. Reaction schemes were proposed to explain the formation of some molecules.

Reaction kinetics of the CN radical with methyl bromide

Hodny, Michael,Hershberger, John F.

, p. 88 - 91 (2016)

The kinetics of the CN + CH3Br reaction were studied using transient infrared laser absorption spectroscopy to detect CN reactants and HCN products. This reaction has a rate constant of k = (2.20 ± 0.6) × 10-12 exp (453 ± 98/T) cm3 molecule-1 s-1 over the range 298-523 K. Hydrogen abstraction to produce HCN + CH2Br is only a minor reaction product, with a branching fraction of 0.12 ± 0.02. Other product channels, including BrCN + CH3, CH2CN + HBr, CH3CN + Br are likely. An upper limit of 0.01 was established for the HBr yield. These results are in qualitative agreement with recent ab initio calculations.

Charge-transfer complexes of hypoglycemic sulfonamide with π-acceptors: Experimental and DFT-TDDFT studies

Soltani, Sara,Magri, Pierre,Rogalski, Marek,Kadri, Mekki

, p. 105 - 116 (2019)

Charge-transfer interactions (CT) between the electron donor gliclazide (GLC) and the π-acceptors 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tetracyanoethylene (TCNE) were studied in a chloroform solution and in the solid state. The CT complexes were discussed in terms of formation constants (KCT), molar extinction coefficients (εCT), standard reaction quantities (ΔG° ΔH° and ΔS°), oscillator strength (f), transition dipole moment (μEN), and ionization potential (Ip). The limits of detection (LOD) and limits of quantification (LOQ) have also been reported. The stoichiometry of these complexes was found to be in a 1:1 M ratio. The formed solid CT complexes were also synthesized and characterized using electronic methods, FT-IR, 1H and 13C NMR spectroscopy. Thermogravimetric analysis techniques (TGA/DTA) and differential scanning calorimetry (DSC) were used to determine the thermal stability of the synthesized CT complex. The kinetic parameters (ΔG* ΔH* and ΔS*) were calculated from thermal decomposition data using the Coats-Redfern method. Moreover, density functional theory (DFT) studies are discussed for the charge transfer complex GLC-TCNE, using the B3LYP with 6–311++G (d, p) basis set. The harmonic vibrational frequencies were calculated, and the scaled values have been compared with experimental FT-IR spectra. The calculated 1H and 13C NMR chemical shifts using the GIAO method showed good correlations with the experimental data. The theoretical UV–visible spectrum of the compound and the electronic properties, such as HOMO and LUMO energies, were performed using the time-dependent (TD-DFT) approach with CAM-B3LYP, employing the 6–311++G (d, p) basis set, and good agreement with the theoretical and experimental UV–visible data was found.

Drost et al.

, p. 189 (1976)

Atakan, B.,Jacobs, A.,Wahl, M.,Weller, R.,Wolfrum, J.

, p. 449 - 453 (1989)

Interaction of HCN/DCN with Si(100)-2X1

Bu, Y.,Ma, L.,Lin, M. C.

, p. 7081 - 7087 (1993)

We have investigated the spectroscopy and reaction of HCN (DCN) adsorbed on Si(100)-2X1 at TS >= 100 K using HREELS, XPS, and UPS.HCN (DCN) formed dimers and/or polymers on the surface at 100 K and higher dosages ( D > 4 langmuirs).The HREEL spectrum obtained after warming 4.5-langmuir HCN dosed surface to 220 K resembles that obtained with a lower HCN dosage (D a peak at 263 meV due to the CN stretching vibration.In the corresponding DCN experiment, the DC=ND stretching mode was observed at 124 meV.Annealing the sample at 560 K appeared to cause the reorientation of the CN radical from an end-on to a side-on adsorption geometry as evidenced by HREELS, UPS, and XPS analyses.At 600-800 K, the breaking of NH and CN bonds occurred on the surface.Above 1000 K, a mixture of silicon carbide and silicon nitride was formed after the complete dissociation of CH, NH, and CN bonds and the desorption of H species.

Gartaganis,Winkler

, p. 1457,1461 (1956)

-

Susz,Hoeffer,Briner

, p. 501 (1941)

-

Temperature Dependence of the Reaction of Nitrogen Atoms with Methyl Radicals

Marston, George,Nesbitt, Fred L.,Nava, David F.,Payne, Walter A.,Stief, Louis J.

, p. 5769 - 5774 (1989)

The discharge-flow mass spectrometry technique has been used to measure the kinetics of the reaction N + CH3 -> products over the temperature range 200-423 K.The results are as follows (10-11 cm3 s-1): k1(200 K)

Becker, K. H.,Engelhardt, B.,Wiesen, P.

, p. 342 - 348 (1989)

Bichowsky

, (1926)

Unconventional CHδ+?N hydrogen bonding interactions in the stepwise solvation of the naphthalene radical cation by hydrogen cyanide and acetonitrile molecules

Platt, Sean P.,Attah, Isaac K.,El-Shall,Hilal, Rifaat,Elroby, Shaaban A.,Aziz, Saadullah G.

, p. 2580 - 2590 (2016)

Equilibrium thermochemical measurements using the mass-selected ion mobility (MSIM) technique have been utilized to investigate the binding energies and entropy changes of the stepwise association of hydrogen cyanide (HCN) and acetonitrile (CH3CN) molecules with the naphthalene radical cation (C10H8?+) in the gas phase forming the C10H8?+(HCN)n and C10H8?+(CH3CN)n clusters with n = 1-3 and 1-5, respectively. The lowest energy structures of the C10H8?+(HCN)n and C10H8?+(CH3CN)n clusters for n = 1-2 have been calculated using the M062X and ω97XD methods within the 6-311+G?? basis set, and for n = 1-6 using the B3LYP method within the 6-311++G?? basis set. In both systems, the initial interaction occurs through unconventional CHδ+?N ionic hydrogen bonds between the hydrogen atoms of the naphthalene cation and the lone pair of electrons on the N atom of the HCN or the CH3CN molecule. The binding energy of CH3CN to the naphthalene cation (11 kcal mol-1) is larger than that of HCN (7 kcal mol-1) due to a stronger ion-dipole interaction resulting from the large dipole moment of CH3CN (3.9 D). On the other hand, HCN can form both unconventional hydrogen bonds with the hydrogen atoms of the naphthalene cation (CHδ+?NCH), and conventional linear hydrogen bonding chains involving HCN?HCN interactions among the associated HCN molecules. HCN molecules tend to form externally solvated structures with the naphthalene cation where the naphthalene ion is hydrogen bonded to the exterior of an HCN?HCN chain. For the C10H8?+(CH3CN)n clusters, internally solvated structures are favored where the acetonitrile molecules are directly interacting with the naphthalene cation through CHδ+?N unconventional ionic hydrogen bonds. In both the C10H8?+(HCN)n and C10H8?+(CH3CN)n clusters, the sequential binding energy decreases stepwise to about 6-7 kcal mol-1 by three HCN or CH3CN molecules, approaching the macroscopic enthalpy of vaporization of liquid HCN (6.0 kcal mol-1).

Surface chemistry of CN bond formation from carbon and nitrogen atoms on Pt(111)

Herceg, Eldad,Trenary, Michael

, p. 17560 - 17566 (2005)

The mechanism of CN bond formation from CH3 and NH3 fragments adsorbed on Pt(111) was investigated with reflection absorption infrared spectroscopy (RAIRS), temperature-programmed desorption (TPD), and X-ray photoelectron spectroscopy (XPS). The surface chemistry of carbon-nitrogen coupling is of fundamental importance to catalytic processes such as the industrial-scale synthesis of HCN from CH4 and NH3 over Pt. Since neither CH4 nor NH3 thermally dissociate on Pt(111) under ultrahigh vacuum (UHV) conditions, the relevant surface intermediates were generated through the thermal decomposition of CH 3I and the electron-induced dissociation of NH3. The presence of surface CN is detected with TPD through HCN desorption as well as with RAIRS through the appearance of the vibrational features characteristic of the aminocarbyne (CNH2) species, which is formed upon hydrogenation of surface CN at 300 K. The RAIRS results show that HCN desorption at a??500 K is kinetically limited by the formation of the CN bond at this temperature. High coverages of Cads suppress CN formation, but the results are not influenced by the coadsorbed I atoms. Cyanide formation is also observed from the reaction of adsorbed N atoms and carbon produced from the dissociation of ethylene. ? 2005 American Chemical Society.

Kroepelin,Vogel

, p. 10 (1936)

-

Garner,Matsuno

, p. 1903 (1921)

-

-

Makovky,Gruenwald

, p. 952,954 (1959)

-

Herries, D. G.,Richards, F. M.

, p. 1155 - 1156 (1964)

Haggart,Winkler

, p. 1791 (1959)

Suarez, M. Patricia,Loeffler, Daniel G.

, p. 240 - 242 (1986)

Chesnavich,Bowers

, p. 1705,1709 (1977)

-

Onyszchuk,Winkler

, p. 368,369 (1955)

-

Trick,Winkler

, p. 915 (1952)

The hexacyanotitanate ion: Synthesis and crystal structure of [NEt4]3[Ti(III)(CN)6]·4MeCN

Entley, William R.,Treadway, Christopher R.,Wilson, Scott R.,Girolami, Gregory S.

, p. 6251 - 6258 (1997)

The hexacyanotitanate salt, [Et4N]3[Ti(CN)6]·4MeCN, has been prepared by addition of tetraethylammonium cyanide to the titanium(III) triflate salt Ti(O3SCF3)3(MeCN)3. The orange crystalline product has been characterized by X-ray diffraction, and the d1 anion is only slightly distorted from ideal O(h) symmetry. The anion resides on a center of symmetry and is characterized by the following parameters: Ti-C = 2.195(2), 2.197(3), and 2.213(3) A?; C-N (av) = 1.141(4) A?; C-Ti-C (cis) = 88.01(9), 88.02(9), 89.02(9), and 89.78(9)°; C-Ti-C (trans) = 180°. In addition to the crystallographic study, details of the IR (ν(CN) = 2071 cm-1), EPR, and UV-vis spectra (Δ(o) = 22800 cm-1) are given. Crystal data for [Et4N]3[Ti(CN)6]·4MeCN are as follows: monoclinic, space group I2/a, a = 18.171(6) A?, b = 12.200(4) A?, c = 20.989(5) A?, β = 91.17(2)°, V = 4652(2) A?3, Z = 4, wR2 = 0.2054 for 3831 data, 27 restraints, and 318 parameters.

The tetracyanoboronic acids H[B(CN)4]·n H 2O9 n = 0, 1, 2

Kueppers, Torsten,Bernhardt, Eduard,Lehmann, Christian W.,Willner, Helge

, p. 1666 - 1672 (2007)

Treatment of an aqueous solution of Na[B(CN)4] with an acidic cation exchange resin leads to a solution of the strong tetracyanoboronic acid. Evaporation of the solution at room temperature yields colourless single crystals of [H5O2][B(CN)4] (P4n2, a = 9.5830(2) A, c = 14.25440(3) A, Z = 1). Further drying of [H 5O2][B(CN)4] (mp. 115 °C) in vacuum at 50 °C gives polycrystalline [H3O][B(CN)4] (P6 3mc, a = 8.704(1) A, c = 6.152(1) A, Z = 2), which is thermally stable up to 145 °C The anhydrous polycrystalline acid H[B(CN)4] is formed quantitatively by reacting Me 3SiNCB(CN)3 with gaseous HCl. This acid starts to decompose at 190 °C with loss of HCN. All three acids were further characterized by vibrational spectroscopy, and elemental analysis.

Mueller

, p. 3459 (1955)

Koenig,Hubbuch

, p. 221 (1922)

Characterization of a carbon-nitrogen network solid with NMR and high field EPR

Rovnyak, David,Baldus, Marc,Itin, Boris A.,Bennati, Marina,Stevens, Andrew,Griffin, Robert G.

, p. 9817 - 9822 (2000)

Considerable attention has been focused on developing a synthetic route to a carbon-nitrogen material with mechanical and thermal properties comparable or superior to those of diamond. To date, no substance with the desired C3N4 stoichiometry in a silicon-nitride crystal lattice has been reported. One of the principal difficulties in the pursuit of ultrahard carbon-nitrogen (CN) solids is the characterization of amorphous CN samples. We describe a solid-state NMR study of a paracyanogen-like solid utilizing 13C-15N adiabatic-passage Hartmann-Hahn cross-polarization (APHH-CP) to perform dipolar filtering and show that this method is well-suited for recoupling 13C-15N in network solids. In addition, high-frequency electron paramagnetic resonance (EPR) indicates a density of electron spins of approximately 1 × 1017 e-/cm3. We conclude by discussing how NMR and EPR data may be useful for optimizing CN-polymer samples as potential precursors for ultrahard carbon nitrogen solids.

Electron and anion mobility in low density hydrogen cyanide gas. I. Dipole-bound electron ground states

Klahn,Krebs

, p. 531 - 542 (1998)

We measured the mobility of excess electrons in the polar hydrogen cyanide gas (D=2.985 D) at low densities as a function of density and temperature by the so-called pulsed Townsend method. Experiments were performed at 294 and 333 K in the gas number density range 1.23×1017≤n≤3.61×1018 cm-3. We found a strong density dependence of the zero-field density-normalized mobility (μn). Only about 10% of the observed density variation can be qualitatively explained by coherent and incoherent multiple scattering effects. With increasing gas density an increasing number of linear HCN dimers is formed which due to the high dipole moment (D=6.552 D) represent much stronger electron scatterers than the HCN monomers. It was found that the dimers may be only in part responsible for the observed density effect. Therefore, we consider a transport process where short-lived dipole-bound electron ground states (lifetime ≥12 ps) as quasilocalized states are involved. For comparison the electron mobility in saturated 2-aminoethanol vapor with a dipole moment of similar size (D=3.05 D) does not show any anomalous density behavior in the temperature range 298≤T≤435 K. In contrast to this the electron mobility in saturated but also in nonsaturated CH3CN gas (D=3.925 D) shows a density behavior similar to that in HCN.

-

Fosse,Hieulle

, (1922)

-

Rate constants for CN reactions with hydrocarbons and the product HCN vibrational populations: Examples of heavy-light-heavy abstraction reactions

Copeland, Leon R.,Mohammad, Fida,Zahedi, Mansour,Volman, David H.,Jackson, William M.

, p. 5817 - 5826 (1992)

The rate constants for the reactions of CN radicals with methane, ethane, propane, cyclopropane, isobutane, and neopentane have been measured over a temperature range from 275 to 455 K.Laser photolysis was used to produce the radicals and time delayed laser induced fluorescence was used to follow the radical concentration as a function of time.The temperature dependence of the observed rate constant could be fitted with a three-parameter Arrhenius plot.The activation energies that were observed were all small and in some cases they were negative.Time resolved ir emission was used to follow the formation of the HCN(0n2) and HCN (0n'1) product emission.The time dependence of the relative emission intensities, as well as computer modeling of the decay curves, suggest that vibrational population inversion occurs for all of the hydrocarbons studied except methane and cyclopropane.These observations are discussed in terms of the current theories for these type of reactions.

Hasenberg, D.,Schmidt, L. D.

, p. 441 - 453 (1987)

Kinetics of the Reaction of N(4S) with Isobutane

Blatt, Christopher S.,Roscoe, Sharon G.,Roscoe, John M.

, p. 2921 - 2924 (1991)

The kinetics of the reaction of isobutane with N(4S) have been studied as a function of reactant concentration and temperature from 300 to 550 K.The initial rate of consumption of N(4S) was second order in N(4S) and first order in isobutane.The initiation step which best describes the results is N + N + i-C4H10 -> N2 + CH3 + 2-C2H7 and its rate constant fits the expression k = 2.26 * 1017 exp(-3890/T) dm6 mol-2 s-1 A mechanism is proposed for the reaction which quantitatively accounts for the consumption of N(4S) and the production of HCN as a function of both temperature and time.HCN arises in this mechanism from reactions of N(4S) with CH3, 2-C3H7 and other alkyl radicals formed in subsequent reactions.

Guernsey et al.

, (1926)

Decomposition of tetramethylammonium cyanosulfite and crystal structures of [(CH3)4N]+HSO4- ·SO2 and [(CH3)4N+]2S2O 72-·2 SO2

Kornath, Andreas,Doz, Priv-,Blecher, Oliver

, p. 625 - 631 (2002)

Tetramethylammonium cyanosulfite decomposes in SO2 at -70°C to give HCN, [(CH3)4N]+HSO4- ·SO2 and [(CH3)4N+]2S2O 72-·2 SO2. A reaction sequence for the decomposition is discussed. The formed salts are characterized by infrared, Raman spectroscopy, and single crystal X-ray diffraction. [(CH3)4N]+HSO4- ·SO2 crystallizes in the monoclinic space group P21/n with a = 709.2(1) pm, b = 1479.7(1) pm, c = 989.6(1) pm, β = 90.86(1)° and four formula units per unit cell. [(CH3)4N+]2S2O 72-·2 SO2 crystallizes in the monoclinic space group P21/n with a = 1212.9(1) pm, b = 1970.1(1) pm, c = 1773.8(1) pm, β = 109.42(1)° and eight formula units per unit cell.

Bassett, H.,Corbet, A. S.

, p. 1358 - 1358 (1924)

Voorhoeve et al.

, p. 297,298-303 (1976)

Facile Synthesis of the Dicyanophosphide Anion via Electrochemical Activation of White Phosphorus: An Avenue to Organophosphorus Compounds

Liu, Liu Leo,Mei, Yanbo,Yan, Zeen

supporting information, p. 1517 - 1522 (2022/02/01)

Organophosphorus compounds (OPCs) have gained tremendous interest in the past decades due to their wide applications ranging from synthetic chemistry to materials and biological sciences. We describe herein a practical and versatile approach for the trans

Tris(pentafluorophenyl)borane-Catalyzed Formal Cyanoalkylation of Indoles with Cyanohydrins

Kiyokawa, Kensuke,Minakata, Satoshi,Urashima, Naruyo

, p. 8389 - 8401 (2021/06/28)

Despite the significant achievements related to the C3 functionalization of indoles, cyanoalkylation reactions continue to remain rather limited. We herein report on the formal C3 cyanoalkylation of indoles with cyanohydrins in the presence of a tris(pentafluorophenyl)borane (B(C6F5)3) catalyst. It is noteworthy that cyanohydrins are used as a cyanoalkylating reagent in the present reaction, even though they are usually used as only a HCN source. Mechanistic investigations revealed the unique reactivity of the B(C6F5)3 catalyst in promoting the decomposition of a cyanohydrin by a Lewis acidic activation through the coordination of the cyano group to the boron center. In addition, a catalytic three-component reaction using indoles, aldehydes as a carbon unit, and acetone cyanohydrin that avoids the discrete preparation of each aldehyde-derived cyanohydrin is also reported. The developed methods provide straightforward, highly efficient, and atom-economic access to various types of synthetically useful indole-3-acetonitrile derivatives containing α-tertiary or quaternary carbon centers.

Large Faraday Rotation in Optical-Quality Phthalocyanine and Porphyrin Thin Films

Nelson, Zachary,Delage-Laurin, Leo,Peeks, Martin D.,Swager, Timothy M.

supporting information, p. 7096 - 7103 (2021/05/29)

The magneto-optical phenomenon known as Faraday rotation involves the rotation of plane-polarized light as it passes through an optical medium in the presence of an external magnetic field oriented parallel to the direction of light propagation. Faraday rotators find applications in optical isolators and magnetic-field imaging technologies. In recent years, organic thin films comprised of polymeric and small-molecule chromophores have demonstrated Verdet constants, which measure the magnitude of rotation at a given magnetic field strength and material thickness, that exceed those found in conventional inorganic crystals. We report herein the thin-film magnetic circular birefringence (MCB) spectra and maximum Verdet constants of several commercially available and newly synthesized phthalocyanine and porphyrin derivatives. Five of these species achieved maximum Verdet constant magnitudes greater than 105 deg T-1 m-1 at wavelengths between 530 and 800 nm. Notably, a newly reported zinc(II) phthalocyanine derivative (ZnPc-OT) reached a Verdet constant of -33 × 104 deg T-1 m-1 at 800 nm, which is among the largest reported for an organic material, especially for an optical-quality thin film. The MCB spectra are consistent with resonance-enhanced Faraday rotation in the region of the Q-band electronic transition common to porphyrin and phthalocyanine derivatives, and the Faraday A-term describes the electronic origin of the magneto-optical activity. Overall, we demonstrate that phthalocyanines and porphyrins are a class of rationally designed magneto-optical materials suitable for applications demanding large Verdet constants and high optical quality.

Catalytic Enantioselective Strecker Reaction of Isatin-Derived N-Unsubstituted Ketimines

Kadota, Tetsuya,Sawa, Masanao,Kondo, Yuta,Morimoto, Hiroyuki,Ohshima, Takashi

supporting information, p. 4553 - 4558 (2021/06/28)

A catalytic enantioselective Strecker reaction of isatin-derived N-unsubstituted ketimines directly afforded the N-unprotected α-aminonitriles with a tetrasubstituted carbon stereocenter in up to 99% ee without requiring protection/deprotection steps. One-pot Strecker reactions from the parent carbonyl compounds were also realized with comparable yields and enantioselectivities. Direct transformations of the N-unprotected α-aminonitrile products streamlined the synthesis of unnatural amino acid derivatives and achieved the shortest one-pot stereoselective routes to a biologically active compound reported to date.

Trapping of Br?nsted acids with a phosphorus-centered biradicaloid - synthesis of hydrogen pseudohalide addition products

Beer, Henrik,Bl?sing, Kevin,Bresien, Jonas,Chojetzki, Lukas,Schulz, Axel,Stoer, Philip,Villinger, Alexander

supporting information, p. 13655 - 13662 (2020/10/27)

The trapping of classical hydrogen pseudohalides (HX, X = pseudohalogen = CN, N3, NCO, NCS, and PCO) utilizing a phosphorus-centered cyclic biradicaloid, [P(μ-NTer)]2, is reported. These formal Br?nsted acids were generatedin situas gases and passed over the trapping reagent, the biradicaloid [P(μ-NTer)]2, leading to the formation of the addition product [HP(μ-NTer)2PX] (successful for X = CN, N3, and NCO). In addition to this direct addition reaction, a two-step procedure was also applied because we failed in isolating HPCO and HNCS addition products. This two-step process comprises the generation and isolation of the highly reactive [HP(μ-NTer)2PX]+cation as a [B(C6F5)4]?salt, followed by salt metathesis with salts such as [cat]X (cat = PPh4,n-Bu3NMe), which also gives the desired [HP(μ-NTer)2PX] product, with the exception of the reaction with the PCO?salt. In this case, proton migration was observed, finally affording the formation of a [3.1.1]-hetero-propellane-type cage compound, an OC(H)P isomer of a HPCO adduct. All discussed species were fully characterized.

Process route upstream and downstream products

Process route

ethanedinitrile
460-19-5,25215-76-3

ethanedinitrile

salicylonitrile
611-20-1

salicylonitrile

hydrogen cyanide
74-90-8

hydrogen cyanide

m-cyanophenol
873-62-1

m-cyanophenol

4-cyanophenol
767-00-0

4-cyanophenol

benzonitrile
100-47-0

benzonitrile

Conditions
Conditions Yield
Product distribution; plasma apparatus; a variety of substituted benzenes and pyridine similarly cyanated;
18 % Chromat.
10 % Chromat.
8.3 % Chromat.
9.0 % Chromat.
diethyl ether
60-29-7,927820-24-4

diethyl ether

2-bromo-2-ethylbutanamide
511-70-6

2-bromo-2-ethylbutanamide

hydrogen cyanide
74-90-8

hydrogen cyanide

2-pentanol
584-02-1

2-pentanol

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
bromocyane
506-68-3

bromocyane

thiourea
17356-08-0

thiourea

hydrogen cyanide
74-90-8

hydrogen cyanide

formamidine disulfide
3256-06-2

formamidine disulfide

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
bromocyane
506-68-3

bromocyane

water
7732-18-5

water

hydrogen cyanide
74-90-8

hydrogen cyanide

sulfuric acid
7664-93-9

sulfuric acid

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
cyanogen iodide
506-78-5

cyanogen iodide

sulphurous acid
7782-99-2

sulphurous acid

hydrogen cyanide
74-90-8

hydrogen cyanide

sulfuric acid
7664-93-9

sulfuric acid

hydrogen iodide
10034-85-2

hydrogen iodide

Conditions
Conditions Yield
tetrachloromethane
56-23-5

tetrachloromethane

bromocyane
506-68-3

bromocyane

hydrogen iodide
10034-85-2

hydrogen iodide

hydrogen cyanide
74-90-8

hydrogen cyanide

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
at 25 ℃; Geschwindigkeit;
bromocyane
506-68-3

bromocyane

water
7732-18-5

water

hydrogen iodide
10034-85-2

hydrogen iodide

hydrogen cyanide
74-90-8

hydrogen cyanide

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
at 25 ℃;
2-bromo-propionic acid amide
5875-25-2

2-bromo-propionic acid amide

hydrogen cyanide
74-90-8

hydrogen cyanide

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

acetaldehyde
75-07-0,9002-91-9

acetaldehyde

Conditions
Conditions Yield
2-bromo-propionic acid amide
5875-25-2

2-bromo-propionic acid amide

hydrogen cyanide
74-90-8

hydrogen cyanide

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

acetaldehyde
75-07-0,9002-91-9

acetaldehyde

Conditions
Conditions Yield
2-bromobutyramide
5398-24-3

2-bromobutyramide

hydrogen cyanide
74-90-8

hydrogen cyanide

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

propionaldehyde
123-38-6

propionaldehyde

Conditions
Conditions Yield

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