| | | BENZANILIDE | PRODUCT IDENTIFICATION | CAS NO. | 93-98-1 | | EINECS NO. | 202-292-7 | | FORMULA | C6H5NHCOC6H5 | | MOL WT. | 197.24 | | H.S. CODE | | | SMILES | | | TOXICITY | | | SYNONYMS | N-Phenyl Benzamide; N-Phenylbenzoic acid amide; | Benzanilid (German); Benzanilida (Spanish); Benzanilide (French); N-Benzoylaniline; N-Phenylbenzamide | CLASSIFICATION | | PHYSICAL AND CHEMICAL PROPERTIES | PHYSICAL STATE | white to grey crystals | MELTING POINT | 163 C | BOILING POINT | | SPECIFIC GRAVITY | 1.315 | SOLUBILITY IN WATER | Insoluble (soluble in alcohol) | pH | | VAPOR DENSITY | | AUTOIGNITION | | NFPA RATINGS | Health: 1; Flammability: 0; Reactivity: 0 | REFRACTIVE INDEX | | FLASH POINT | 180 C | STABILITY | Stable under ordinary conditions. | GENERAL DESCRIPTION & APPLICATIONS | Amide is a group of organic chemicals with the general formula RCO-NH2 in which a carbon atom is attached to oxygen in solid bond and also attached to an hydroxyl group, where 'R' groups range from hydrogen to various linear and ring structures or a compound with a metal replacing hydrogen in ammonia such as sodium amide, NaNH2. Amides are divided into subclasses according to the number of substituents on nitrogen. The primary amide is formed from by replacement of the carboxylic hydroxyl group by the NH2, amino group. An example is acetamide (acetic acid + amide). Amide is obtained by reaction of an acid chloride, acid anhydride, or ester with an amine. Amides are named with adding '-ic acid' or '-oic acid' from the name of the parent carboxylic acid and replacing it with the suffix 'amide'. Amide can be formed from ammonia (NH3). The secondary and tertiary amides are the compounds which one or both hydrogens in primary amides are replaced by other groups. The names of secondary and tertiary amides are denoted by the replaced groups with the prefix capital N (meaning nitrogen) prior to the names of parent amides. Low molecular weight amides are soluble in water due to the formation of hydrogen bonds. primary amides have higher melting and boiling points than secondary and tertiary amides. Anilide is an amide derived from aniline by substitution of an acyl group for the hydrogen of NH2. Acetanilide is from acetic acid and aniline. Acetanilide is an odourless, white flake solid or crystalline powder (pure form); soluble in hot water alcohol, ether, chloroform, acetone, glycerol, and benzene;; melting point 114 C and boiling point 304 C; can undergo self-ignite at 545 C, but is otherwise stable under most conditions. Acetanilide which can be obtained by acetylation of aniline undergoes nitration at low temperature and yields highly the para-nitro products. Acetyl group can then be removed by acid-catalyzed hydrolysis to yield para-nitroaniline. Although the activating affection of the amino group can be reduced, the acetyl derivative remains an ortho/para-orientation and activating substituent. Examples of aromatic anilide are benzanilide, C6H5NHCOC6H5 or Carbanilide (N,N'-diphenylcarbamide). Some structural amides are; * Acetamides * Acrylamides * Anilides * Benzamides * Naphthylamides * Formamides * Lactams * Salicylamides * Sulfonamides * Thioamides * Fatty amidesAn amide is hydrolyzed to yield an amine and a carboxylic acid under strong acidic conditions. The reverse of this process resulting in the loss of water to link amino acids is wide in nature to form proteins, the principal constituents of the protoplasm of all cells. Acyl halides are the most reactive but amides the least reactive among carboxylic acid derivatives, as in order of "acyl halides > anhydrides > esters ¡Ã acids > amides". In homogeneous solvent systems, amides react with water only in the presence of strong acid or base catalysts under heating. Because of the nitrogen non-bonded electron pair with the carbonyl group, amides are very polar and the basicity is weaker than amines. Electrophiles bond to oxygen atom in preference to the nitrogen in an amide. One example of this reaction is the production of nitriles by dehydration of primary amides when treated with thionyl chloride. The addition of water to nitriles (carbon-nitrogen triple bond) gives an amide.Sulfonamides are analogs of amides in which the atom attached to oxygen in solid bond is sulfur rather than carbon. Sulfonamides react with alkyl halides, acid halides, sulfonyl halides, epihalohydrins, ketones and aldehydes under basic conditions. Benzamide, the simplest aromatic carboxylic amide, is used in the synthesis of various organic compounds. Polyamide is a polymer containing repeated amide gr-------------------------------------------------
NitrationFrom Wikipedia, the free encyclopediaNitration is a general class of chemical process for the introduction of a nitro group into an organic chemical compound. More loosely the term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid, as occurs in the synthesis of nitroglycerin. The difference between the resulting structure of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, typically carbon or another nitrogen atom, whereas in nitrate esters, also called organic nitrates, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.There are many major industrial applications of nitration in the strict sense; the most important by volume are for the production of Nitroaromatic compounds such as nitrobenzene. Nitration reactions are notably used for the production of explosives, for example the conversion of guanidine to nitroguanidine and the conversion of toluene to trinitrotoluene. However, they are of wide importance as chemical intermediates and precursors. Millions of tons of nitroaromatics are produced annually.[1]Contents [hide] * 1Aromatic nitration * 2Scope * 3Ipso nitration * 4References-------------------------------------------------
Aromatic nitration[edit]Typical nitration syntheses apply so-called "mixed acid", a mixture of concentrated nitric acid and sulfuric acids.[2] This mixture produces the nitronium ion (NO2+), which is the active species in aromatic nitration. This active ingredient, which can be isolated in the case of nitronium tetrafluoroborate,[3] also effects nitration without the need for the mixed acid. In mixed-acid syntheses sulfuric acid is not consumed and hence acts as a catalyst as well as an absorbent for water. In the case of nitration of benzene, the reaction is conducted at 50 °C.[citation needed] The process is one example of electrophilic aromatic substitution, which involves the attack by the electron-rich benzene ring:Alternative mechanisms have also been proposed, including one involving single electron transfer (SET).[4][5]-------------------------------------------------
Scope[edit]Selectivity can be a challenge in nitrations because as a rule more than one compound may result but only one is desired, so alternative products act as contaminants or are simply wasted. Accordingly, it is desirable to design syntheses with suitable selectivity; for example, by controlling the reaction conditions, fluorenone can be selectively trinitrated[6]or tetranitrated.[7]Another example of selective trinitration is when benzene is symmetrically trinitrated to 1,3,5 trinitrobenzene to produce a precursor for the synthesis of phloroglucinol.The substituents on aromatic rings affect the rate of this electrophilic aromatic substitution. Deactivating groups such as other nitro groups have an electron-withdrawing effect. Such groups deactivate (slow) the reaction and directs the electrophilic nitronium ion to attack the aromatic meta position. Deactivating meta-directoring substituents includesulfonyl, cyano groups, keto, esters, and carboxylates. Nitration can be accelerated by activating groups such as amino, hydroxy and methyl groups also amides and ethersresulting in para and ortho isomers.The direct nitration of aniline with nitric acid and sulfuric acid, according to one source [8] results in a 50/50 mixture of para and meta nitroaniline. In this reaction the fast-reacting and activating aniline (ArNH2) exists in equilibrium with the more abundant but less reactive (deactivated) anilinium ion (ArNH3+), which may explain this reaction product distribution. According to another source [9] a more controlled nitration of aniline starts with the formation of acetanilide by reaction with acetic anhydride followed by the actual nitration. Because the amide is a regular activating group the products formed are the para and ortho isomers. Heating the reaction mixture is sufficient to hydrolyze the nitroamide back to the nitroamine.In the Wolfenstein-Boters reaction, benzene reacts with nitric acid and mercury nitrate to give picric acid.-------------------------------------------------
Ipso nitration[edit]With aryl chlorides, triflates and nonaflates ipso substitution can take place as well in so-called ipso nitration.[10] The phrase was first used by Perrin and Skinner in 1971 in an investigation into chloroanisole nitration [11] In one protocol 4-chloro-n-butylbenzene is reacted with sodium nitrite in t-butanol in presence of 0.5 mol% Pd2(dba)3, a biarylphosphine ligand and a phase-transfer catalyst to 4-nitro-n-butylbenzene [12]-------------------------------------------------
References[edit] 1. Jump up^ Gerald Booth "Nitro Compounds, Aromatic" Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_411 2. Jump up^ John McMurry Organic Chemistry 2nd Ed. 3. Jump up^ George A. Olah and Stephen J. Kuhn. "Benzonitrile, 2-methyl-3,5-dinitro-". Org. Synth.; Coll. Vol. 5, p. 480 4. Jump up^ Esteves, P. M.; Carneiro, J. W. M.; Cardoso, S. P.; Barbosa, A. G. H.; Laali, K. K.; Rasul, G.; Prakash, G. K. S.; e Olah, G. A. (2003). "Unified Mechanism Concept of Electrophilic Aromatic Nitration Revisited: Convergence of Computational Results and Experimental Data". J. Am. Chem. Soc. 125 (16): 4836–49. doi:10.1021/ja021307w. PMID 12696903. 5. Jump up^ Queiroz, J. F.; Carneiro, J. W. M.; Sabino A. A.; Sparapan, R.; Eberlin, M. N.; Esteves, P. M. (2006). "Electrophilic Aromatic Nitration: Understanding Its Mechanism and Substituent Effects". J. Org. Chem. 71 (16): 6192–203. doi:10.1021/jo0609475. PMID 16872205. 6. Jump up^ E. O. Woolfolk and Milton Orchin. "2,4,7-Trinitrofluorenone". Org. Synth.; Coll. Vol. 3, p. 837 7. Jump up^ Melvin S. Newman and H. Boden. "2,4,5,7-Tetranitrofluorenone". Org. Synth.; Coll. Vol. 5, p. 1029 8. Jump up^ Web resource: warren-wilson.edu 9. Jump up^ Mechanism and synthesis Peter Taylor,Royal Society of Chemistry (Great Britain),Open University 10. Jump up^ Prakash, G.; Mathew, T. (2010). "Ipso-Nitration of Arenes". Angewandte Chemie (International ed. in English) 49 (10): 1726–1728. doi:10.1002/anie.200906940. PMID 20146295. 11. Jump up^ Perrin, C. L.; Skinner, G. A. (1971). "Directive effects in electrophilic aromatic substitution ("ipso factors"). Nitration of haloanisoles". Journal of the American Chemical Society 93 (14): 3389. doi:10.1021/ja00743a015. 12. Jump up^ Fors, B.; Buchwald, S. (2009). "The Pd-Catalyzed Conversion of Aryl Chlorides, Triflates, and Nonaflates to Nitroaromatics". Journal of the American Chemical Society 131 (36): 12898–12899. doi:10.1021/ja905768k. PMC 2773681. PMID 19737014.Categories: * Substitution reactions-------------------------------------------------
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NitrationFrom Wikipedia, the free encyclopediaNitration is a general class of chemical process for the introduction of a nitro group into an organic chemical compound. More loosely the term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid, as occurs in the synthesis of nitroglycerin. The difference between the resulting structure of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, typically carbon or another nitrogen atom, whereas in nitrate esters, also called organic nitrates, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.There are many major industrial applications of nitration in the strict sense; the most important by volume are for the production of Nitroaromatic compounds such as nitrobenzene. Nitration reactions are notably used for the production of explosives, for example the conversion of guanidine to nitroguanidine and the conversion of toluene to trinitrotoluene. However, they are of wide importance as chemical intermediates and precursors. Millions of tons of nitroaromatics are produced annually.[1]Contents [hide] * 1Aromatic nitration * 2Scope * 3Ipso nitration * 4References-------------------------------------------------
Aromatic nitration[edit]Typical nitration syntheses apply so-called "mixed acid", a mixture of concentrated nitric acid and sulfuric acids.[2] This mixture produces the nitronium ion (NO2+), which is the active species in aromatic nitration. This active ingredient, which can be isolated in the case of nitronium tetrafluoroborate,[3] also effects nitration without the need for the mixed acid. In mixed-acid syntheses sulfuric acid is not consumed and hence acts as a catalyst as well as an absorbent for water. In the case of nitration of benzene, the reaction is conducted at 50 °C.[citation needed] The process is one example of electrophilic aromatic substitution, which involves the attack by the electron-rich benzene ring:Alternative mechanisms have also been proposed, including one involving single electron transfer (SET).[4][5]-------------------------------------------------
Scope[edit]Selectivity can be a challenge in nitrations because as a rule more than one compound may result but only one is desired, so alternative products act as contaminants or are simply wasted. Accordingly, it is desirable to design syntheses with suitable selectivity; for example, by controlling the reaction conditions, fluorenone can be selectively trinitrated[6]or tetranitrated.[7]Another example of selective trinitration is when benzene is symmetrically trinitrated to 1,3,5 trinitrobenzene to produce a precursor for the synthesis of phloroglucinol.The substituents on aromatic rings affect the rate of this electrophilic aromatic substitution. Deactivating groups such as other nitro groups have an electron-withdrawing effect. Such groups deactivate (slow) the reaction and directs the electrophilic nitronium ion to attack the aromatic meta position. Deactivating meta-directoring substituents includesulfonyl, cyano groups, keto, esters, and carboxylates. Nitration can be accelerated by activating groups such as amino, hydroxy and methyl groups also amides and ethersresulting in para and ortho isomers.The direct nitration of aniline with nitric acid and sulfuric acid, according to one source [8] results in a 50/50 mixture of para and meta nitroaniline. In this reaction the fast-reacting and activating aniline (ArNH2) exists in equilibrium with the more abundant but less reactive (deactivated) anilinium ion (ArNH3+), which may explain this reaction product distribution. According to another source [9] a more controlled nitration of aniline starts with the formation of acetanilide by reaction with acetic anhydride followed by the actual nitration. Because the amide is a regular activating group the products formed are the para and ortho isomers. Heating the reaction mixture is sufficient to hydrolyze the nitroamide back to the nitroamine.In the Wolfenstein-Boters reaction, benzene reacts with nitric acid and mercury nitrate to give picric acid.-------------------------------------------------
Ipso nitration[edit]With aryl chlorides, triflates and nonaflates ipso substitution can take place as well in so-called ipso nitration.[10] The phrase was first used by Perrin and Skinner in 1971 in an investigation into chloroanisole nitration [11] In one protocol 4-chloro-n-butylbenzene is reacted with sodium nitrite in t-butanol in presence of 0.5 mol% Pd2(dba)3, a biarylphosphine ligand and a phase-transfer catalyst to 4-nitro-n-butylbenzene [12]-------------------------------------------------
References[edit] 1. Jump up^ Gerald Booth "Nitro Compounds, Aromatic" Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_411 2. Jump up^ John McMurry Organic Chemistry 2nd Ed. 3. Jump up^ George A. Olah and Stephen J. Kuhn. "Benzonitrile, 2-methyl-3,5-dinitro-". Org. Synth.; Coll. Vol. 5, p. 480 4. Jump up^ Esteves, P. M.; Carneiro, J. W. M.; Cardoso, S. P.; Barbosa, A. G. H.; Laali, K. K.; Rasul, G.; Prakash, G. K. S.; e Olah, G. A. (2003). "Unified Mechanism Concept of Electrophilic Aromatic Nitration Revisited: Convergence of Computational Results and Experimental Data". J. Am. Chem. Soc. 125 (16): 4836–49. doi:10.1021/ja021307w. PMID 12696903. 5. Jump up^ Queiroz, J. F.; Carneiro, J. W. M.; Sabino A. A.; Sparapan, R.; Eberlin, M. N.; Esteves, P. M. (2006). "Electrophilic Aromatic Nitration: Understanding Its Mechanism and Substituent Effects". J. Org. Chem. 71 (16): 6192–203. doi:10.1021/jo0609475. PMID 16872205. 6. Jump up^ E. O. Woolfolk and Milton Orchin. "2,4,7-Trinitrofluorenone". Org. Synth.; Coll. Vol. 3, p. 837 7. Jump up^ Melvin S. Newman and H. Boden. "2,4,5,7-Tetranitrofluorenone". Org. Synth.; Coll. Vol. 5, p. 1029 8. Jump up^ Web resource: warren-wilson.edu 9. Jump up^ Mechanism and synthesis Peter Taylor,Royal Society of Chemistry (Great Britain),Open University 10. Jump up^ Prakash, G.; Mathew, T. (2010). "Ipso-Nitration of Arenes". Angewandte Chemie (International ed. in English) 49 (10): 1726–1728. doi:10.1002/anie.200906940. PMID 20146295. 11. Jump up^ Perrin, C. L.; Skinner, G. A. (1971). "Directive effects in electrophilic aromatic substitution ("ipso factors"). Nitration of haloanisoles". Journal of the American Chemical Society 93 (14): 3389. doi:10.1021/ja00743a015. 12. Jump up^ Fors, B.; Buchwald, S. (2009). "The Pd-Catalyzed Conversion of Aryl Chlorides, Triflates, and Nonaflates to Nitroaromatics". Journal of the American Chemical Society 131 (36): 12898–12899. doi:10.1021/ja905768k. PMC 2773681. PMID 19737014.Categories: * Substitution reactions-------------------------------------------------
Navigation menu * Create account * Not logged in * Talk * Contributions * Log in * Article * Talk * Read * Edit * View history-------------------------------------------------
Top of FormBottom of Form * Main page * Contents * Featured content * Current events * Random article * Donate to Wikipedia * Wikipedia storeInteraction * Help * About Wikipedia * Community portal * Recent changes * Contact pageTools * What links here * Related changes * Upload file * Special pages * Permanent link * Page information * Wikidata item * Cite this pagePrint/export * Create a book * Download as PDF * Printable versionLanguages * العربية * Català * Čeština * Deutsch * Eesti * Español * فارسی * Français * Հայերեն * Italiano * עברית * Latviešu * Nederlands * Polski * Português * Русский * Slovenčina * Slovenščina * Suomi * Svenska * 中文Edit links * This page was last modified on 29 September 2015, at 16:33. * Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. * Privacy policy * About Wikipedia * Disclaimers * Contact Wikipedia * Developers * Mobile view * * |