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| Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs and other pharmaceuticals, herbicides and pesticides, and in the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers. Some astrobiologists suggest that it may be an alternative to water as the main solvent in other forms of life.
Formamides are compounds of the type RR′NCHO. One important formamide is dimethylformamide, (CH3)2NCHO. |
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| InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3) |
| ZHNUHDYFZUAESO-UHFFFAOYSA-N |
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solvent
A liquid that can dissolve other substances (solutes) without any change in their chemical composition.
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solvent
A liquid that can dissolve other substances (solutes) without any change in their chemical composition.
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View more via ChEBI Ontology
Ameisensäureamid
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ChEBI
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carbamaldehyde
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NIST Chemistry WebBook
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Formamid
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ChEBI
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Formamide
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KEGG COMPOUND
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FORMAMIDE
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PDBeChem
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formamide
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UniProt
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formimidic acid
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ChemIDplus
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Methanamid
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ChEBI
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Methanamide
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KEGG COMPOUND
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505995
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Reaxys Registry Number
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Reaxys
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75-12-7
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CAS Registry Number
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ChemIDplus
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75-12-7
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CAS Registry Number
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NIST Chemistry WebBook
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824
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Gmelin Registry Number
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Gmelin
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Kumaran R, Ramamurthy P (2011)
Photophysical studies on the interaction of formamide and alkyl substituted amides with photoinduced electron transfer (PET) based acridinedione dyes in water.
Journal of fluorescence 21, 2165-2172 [PubMed:21769603]
[show Abstract]
Interaction of photoinduced electron transfer (PET) based acridinedione dye (ADR 1) with amides like formamide, acetamide and dimethylformamide (DMF) were investigated by fluorescence spectral techniques. A fluorescence enhancement accompanied with a blue shift in the emission maximum was observed on the addition of amides to ADR 1 dye, which possess C(6)H(4)(p-OCH(3)) in the 9th position of the basic acridinedione ring. The extent of fluorescence enhancement and the blue shift in the emission maximum of ADR 1 dye is of the order of DMF > acetamide > formamide. DMF, which is more hydrophobic and less polar, results in a higher extent of fluorescence enhancement and a larger shift in the emission maximum towards the blue region. On the addition of amides, the ADR 1 dye prefers to orient towards a more hydrophobic phase surrounded by more number of amide molecules. The fluorescence enhancement of ADR 1 dye is attributed to the suppression of PET process occurring through space. The influence of the hydrophobic nature and the polarity of the amides on the excited state properties of acridinedione dyes are elucidated by steady-state and time resolved fluorescence measurements. | Paarmann A, Lima M, Chelli R, Volkov VV, Righini R, Miller RJ (2011)
Excitonic effects in two-dimensional vibrational spectra of liquid formamide.
Physical chemistry chemical physics : PCCP 13, 11351-11358 [PubMed:21573300]
[show Abstract]
The linear and two-dimensional infrared (2DIR) responses of the amide I vibrational mode in liquid formamide are investigated experimentally and theoretically using molecular dynamics simulations. The recent method based on the numerical integration of the Schrödinger equation is employed to calculate the 2DIR spectra. Special attention is devoted to the interplay of the structural dynamics and the excitonic nature of the amide I modes in determining the optical response of the studied system. In particular, combining experimental data, simulated spectra and analysis of the simulated atomic trajectory in terms of a transition dipole coupling model, we provide a convincing explanation of the peculiar features of the 2DIR spectra, which show a substantial increase of the antidiagonal bandwidth with increasing frequency. We point out that, at variance with liquid water, the 2DIR spectral profile of formamide is determined more by the excitonic nature of the vibrational states than by the fast structural dynamics responsible for the frequency fluctuations. | Weiss AK, Hofer TS, Randolf BR, Bhattacharjee A, Rode BM (2011)
Hydrogen bond formation of formamide and N-methylformamide in aqueous solution studied by quantum mechanical charge field-molecular dynamics (QMCF-MD).
Physical chemistry chemical physics : PCCP 13, 12173-12185 [PubMed:21647491]
[show Abstract]
The formation of hydrogen-bonds of formamide and "cis"-N-methylformamide in aqueous solution was examined using double zeta HF level Quantum Mechanical Charge Field-Molecular Dynamics (QMCF-MD) simulations. Basic attributes such as structure and dynamics of the solvates and hydrogen-bonds were studied in particular by means of coordination number distributions, mean residence times and radial distribution functions, on which spatial restrictions in the form of planes and cones were applied. Advanced methods of analysis gave detailed information about the sterical environment and the dynamic behavior of strong and weak hydrogen-bonds formed by the residues. The comparison of both molecules over a sampling period of 12 ps provided information on the influence of methylation of the amide function on molecular and hydration properties. | Hamann T, Edtbauer A, da Silva FF, Denifl S, Scheier P, Swiderek P (2011)
Dissociative electron attachment to gas-phase formamide.
Physical chemistry chemical physics : PCCP 13, 12305-12313 [PubMed:21647492]
[show Abstract]
Dissociative electron attachment (DEA) to gaseous formamide, HCONH(2), has been investigated in the energy range between 0 eV and 18 eV using a crossed electron/molecule beam technique. The negative ion fragments have been comprehensively monitored and assigned to molecular structures by comparison with the results for two differently deuterated derivatives, namely 1D-formamide, DCONH(2), and N,N,D-formamide, HCOND(2). The following products were observed: HCONH(-), CONH(2)(-), HCON(-), OCN(-), HCNH(-), CN(-), NH(2)(-)/O(-), NH(-), and H(-). NH(2)(-) was also separated from O(-) by using high-resolution negative ion mass spectrometry. Four resonant dissociation channels can be resolved, the strongest ones being located between 2.0 and 2.7 eV and between 6.0 and 7.0 eV. CN(-) as the most abundant fragment and HCONH(-) are the dominant products of the first of these two resonances. The most important products of the latter resonance are NH(2)(-), CN(-), H(-), CONH(2)(-), and OCN(-). It is thus found that the loss of neutral H is a site-selective process, dissociation from the N site taking place between 2.0 and 2.7 eV while dissociation from the C site occurs between 6.0 and 7.0 eV. The suitability of these reactions and thus of formamide as an agent for electron-induced surface functionalisation is discussed. | Karunasekara T, Poole CF (2011)
Models for liquid-liquid partition in the system formamide-organic solvent and their use for estimating descriptors for organic compounds.
Talanta 83, 1118-1125 [PubMed:21215846]
[show Abstract]
Partition coefficients for varied compounds were determined for the organic solvent-formamide biphasic partition system where the organic solvent is 1,2-dichloroethane, 1-octanol or isopentyl ether. These partition coefficient databases are analyzed using the solvation parameter model facilitating a quantitative comparison of the formamide-based partition systems with other totally organic and water-based partition systems. Formamide is shown to be a less cohesive and hydrogen-bond acidic solvent than water with similar hydrogen-bond basicity and dipolarity/polarizability. Compared with other organic solvents its higher cohesion, dipolarity/polarizability and hydrogen-bonding capability make it a useful base solvent for forming biphasic partition systems with a range of system properties obtained through variation of the counter solvent. Formamide-organic solvent systems offer a complementary approach to water-based partition systems for sample preparation and the determination of descriptors for compounds virtually insoluble in water or unstable in water. | Nguyen VS, Abbott HL, Dawley MM, Orlando TM, Leszczynski J, Nguyen MT (2011)
Theoretical study of formamide decomposition pathways.
The journal of physical chemistry. A 115, 841-851 [PubMed:21229996]
[show Abstract]
The chemical transformations of formamide (NH(2)CHO), a molecule of prebiotic interest as a precursor for biomolecules, are investigated using methods of electronic structure computations and Rice-Rampserger-Kassel-Marcus (RRKM) theory. Specifically, quantum chemical calculations applying the coupled-cluster theory CCSD(T), whose energies are extrapolated to the complete basis set limit (CBS), are carried out to construct the [CH(3)NO] potential energy surface. RRKM theory is then used to systematically examine decomposition channels leading to the formation of small molecules including CO, NH(3), H(2)O, HCN, HNC, H(2), HNCO, and HOCN. The energy barriers for the decarboxylation, dehydrogenation, and dehydration processes are found to be in the range of 73-78 kcal/mol. H(2) loss is predicted to be a one-step process although a two-step process is competitive. CO elimination is found to prefer a two-step pathway involving the carbene isomer NH(2)CHO (aminohydroxymethylene) as an intermediate. This CO-elimination channel is also favored over the one-step H(2) loss, in agreement with experiment. The H(2)O loss is a multistep process passing through a formimic acid conformer, which subsequently undergoes a rate-limiting dehydration. The dehydration appears to be particularly favored in the low-temperature regime. The new feature identifies aminohydroxymethylene as a transient but crucial intermediate in the decarboxylation of formamide. | Ferus M, Kubelík P, Civiš S (2011)
Laser spark formamide decomposition studied by FT-IR spectroscopy.
The journal of physical chemistry. A 115, 12132-12141 [PubMed:21932847]
[show Abstract]
High-resolution FT-IR spectroscopy was used for the analysis of the products of formamide dissociation using a high-energy Asterix laser. In the experiment, the detected products of the formamide LIDB dissociation were hydrogen cyanide, ammonia, carbon monoxide, carbon dioxide, nitrous oxide, hydroxylamine, and methanol. The molecular dynamics of the process was simulated with the use of a chemical model. The chemistry shared by formamide and the products of its dissociation is discussed with the respect to the formation of biomolecules. | Zoranić L, Mazighi R, Sokolić F, Perera A (2009)
Concentration fluctuations and microheterogeneity in aqueous amide mixtures.
The Journal of chemical physics 130, 124315 [PubMed:19334838]
[show Abstract]
The relationship between concentration fluctuations and the microheterogeneous status of aqueous amide mixtures is addressed through the molecular dynamics study of three different amides, namely, formamide, N-methylformamide, and dimethylformamide. The computer simulations provide structural evidence that these mixtures exhibit considerable microheterogeneity, in apparent contrast to the experimentally obtained Kirkwood-Buff integrals which indicate that these mixtures should be near ideal. This contradiction is addressed by distinguishing microheterogeneity from concentration fluctuations. The former is the result of mixing H-bonding species under specific constraints due to various bonding possibilities between the molecules, while the second is related to the average relative distribution of the molecules. The relationship between these two different quantities is analyzed and illustrated in terms of the partial site-site structure factors. Small wave-number prepeaks relate to the microheterogeneity while zero wave-number value relates to the concentration fluctuations. A simple analytical statistical model for the microheterogeneity is formulated, which allows to discuss the small wave-number behavior of these structure factors in terms of the kinetics of the transient cluster formation, as observed in the computer simulations. | Liu Y, Hill BC (2007)
Formamide probes a role for water in the catalytic cycle of cytochrome c oxidase.
Biochimica et biophysica acta 1767, 45-55 [PubMed:17184725]
[show Abstract]
Formamide is a slow-onset inhibitor of mitochondrial cytochrome c oxidase that is proposed to act by blocking water movement through the protein. In the presence of formamide the redox level of mitochondrial cytochrome c oxidase evolves over the steady state as the apparent electron transfer rate from cytochrome a to cytochrome a(3) slows. At maximal inhibition cytochrome a and cytochrome c are fully reduced, whereas cytochrome a(3) and Cu(B) remain fully oxidized consistent with the idea that formamide interferes with electron transfer between cytochrome a and the oxygen reaction site. However, transient kinetic studies show that intrinsic rates of electron transfer are unchanged in the formamide-inhibited enzyme. Formamide inhibition is demonstrated for another member of the heme-oxidase family, cytochrome c oxidase from Bacillus subtilis, but the onset of inhibition is much quicker than for mitochondrial oxidase. If formamide inhibition arises from a steric blockade of water exchange during catalysis then water exchange in the smaller bacterial oxidase is more open. Subunit III removal from the mitochondrial oxidase hastens the onset of formamide inhibition suggesting a role for subunit III in controlling water exchange during the cytochrome c oxidase reaction. | Falciola L, Mussini PR, Mussini T, Pelle P (2004)
Determination of primary and secondary standards and characterization of appropriate salt bridges for pH measurements in formamide.
Analytical chemistry 76, 528-535 [PubMed:14750843]
[show Abstract]
For the first time, the standardization for pH measurements is here implemented in the domain of superpermittive media. The nonaqueous solvent studied is formamide (epsilon = 109.5 at 298.15 K) for which three primary standards and two secondary standards have been determined, whose excellent internal consistency has also been demonstrated by specific cell measurements. A comparison of the pH scale in formamide with the aqueous scale has been duly tried by accounting for the primary medium effect on the H+ ion. Furthermore, as a result of an ad hoc supplementary systematic investigation, three salt bridges of appropriate level of equitransference in formamide, that is, NH(4)Cl, NH(4)Br, and NH(4)I, have been characterized for abating the liquid junction potentials intervening in the pH-measuring cell to enable the user to carry out regular pH measurements and related controls. | Augustine-Rauch KA, Zhang Q, Kleinman M, Lawton R, Welsh MJ (2004)
A study of vehicles for dosing rodent whole embryo culture with non aqueous soluble compounds.
Reproductive toxicology (Elmsford, N.Y.) 18, 391-398 [PubMed:15082074]
[show Abstract]
In rodent whole embryo culture (WEC), finding vehicles for non-aqueous-soluble compounds has been problematic due to developmental toxicity associated with many solvents. The purpose of this study was to identify alternative vehicles for insoluble compounds. In WEC, we evaluated carrier solutions containing bovine serum albumin (BSA) and glycerol as well as the solvents, formamide, dimethylformamide (DMF), dimethyl sulfoxide (DMSO) and ethanol, for relative teratogenicity and delivery of the insoluble teratogen, all-trans retinoic acid (RA). At a concentration of | Li J (2002)
Elimination of polymer interference in chromatographic analysis of estradiol degradation products in a transdermal drug delivery formulation by proper selection of extraction solvents.
Journal of pharmaceutical sciences 91, 1873-1879 [PubMed:12115814]
[show Abstract]
This article describes the proper selection of extraction solvents to eliminate interference from a polymer matrix to the quantitation of estradiol degradation products in a transdermal formulation by reversed-phase liquid chromatography. The separation is performed by gradient elution with acetonitrile and water as the mobile phase on Inertsil ODS columns. Severe band distortion and insufficient recovery are observed for two geometric degradation products (or impurities) when the sample is prepared by acetonitrile. It is anticipated that the poor resolution and recovery are caused by multiple retention processes due to the reversible binding of degradation products to the polymer matrix (or the impurity-polymer interaction). This interaction is eliminated by adding formamide, a solvent that possesses similar properties to the matrix, in the extraction solvent. It is believed that the favorable interaction between formamide and the polymer matrix releases the impurity molecules, and they can then be separated by a single retention mode. It has been confirmed experimentally that the use of formamide in the extraction solvent not only sharpens the peaks tremendously, but also recovers the degradation products completely. | Simard C, Lemieux R, Côté S (2001)
Urea substitutes toxic formamide as destabilizing agent in nucleic acid hybridizations with RNA probes.
Electrophoresis 22, 2679-2683 [PubMed:11545392]
[show Abstract]
Since their introduction some three decades ago, methods for hybridization analysis of nucleic acids immobilized on solid supports have evolved to improve the sensitivity, speed, and convenience of their application. However, in many cases these methods still require the use of solutions containing formamide, a recognized hazardous solvent with potential toxicity. Here, we have compared the efficiency of urea to that of formamide as denaturing agent in nucleic acid hybridization with RNA probes. We show that urea at concentrations of 2-4 molar in solution performs as good as 50% formamide to reduce heterologous background hybridization in Northern blotting experiments realized at 68 degrees C. Presence of urea at higher concentrations resulted in reduced hybridization sensitivity, possibly due to increased viscosity. When tested in Southern blot analysis of genomic DNA, our results revealed that the use of urea in hybridization solution is also suitable to carry out single-copy gene detection. Together, these findings show that urea can efficiently and safely replace formamide in solutions. | Sakthivel T, Jaitely V, Patel NV, Florence AT (2001)
Non-aqueous emulsions: hydrocarbon-formamide systems.
International journal of pharmaceutics 214, 43-48 [PubMed:11282235]
[show Abstract]
There are few reports in the literature on formulation of non-aqueous emulsions. This study was designed to evaluate some design criteria for such systems. Formamide is the closest polar solvent that has the ability to replace water in emulsification when employing established non-ionic surfactants as stabilisers. For the majority of studies, linear alkanes (C6-C16) were dispersed in formamide as the continuous phase were stabilised with polysorbate 20. Initial studies involved gentle emulsification and observing mean globule size. The mean globule size varied in a non-linear fashion with alkyl chain length, the minimum being between C10 and C12. Sonication for 30 s led to smaller differences in the mean globule size. The effect of various parameters such as surfactant concentration and solvophilicity of the surfactant was observed. The surface activities of polysorbate 20, 40, 60 and 80 in formamide and critical micellar concentrations were determined. The latter were several orders of magnitude higher in formamide than in water, and the areas per molecule larger. The addition of water to the dodecane formamide systems did not destabilise the emulsion. Release of the model drug dehydroepiandrosterone from dodecane in formamide emulsions was studied in distilled water, the rate of release being dependent on the volume fraction of dodecane. |
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