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Topic: Acyl chloride

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Thionyl chloride

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	Acyl chloride - Wikipedia, the free encyclopedia
		Acyl chlorides are a subset of acyl halides and undergo many of the chemical reactions mentioned under Acyl halide.
		Since a chloride ion is a good leaving group, this is a very useful compound synthetically, it can be used to prepare any carboxylic acid derivative: an acid anhydride, an ester or an amide by reacting acid chlorides with: a salt of a carboxylic acid, an alcohol, or an amine respectively.
		Acyl chlorides are often prepared by reacting a carboxylic acid with thionyl chloride.
	en.wikipedia.org /wiki/Acyl_chloride (362 words)

	Acyl halide - Wikipedia, the free encyclopedia
		An acyl halide (also known as an acid halide or haloformate) is an organic compound containing a -COX functional group, which consists of a carbonyl group singly bonded to a halogen atom such as chlorine ( Cl ;).
		Acyl halides are commonly made by halogenating a carboxylic acid, hence the name acid halide.
		Acyl halides are artificial, rather reactive compounds often synthesized to be used as intermediates in the synthesis of other organic compounds.
	en.wikipedia.org /wiki/Acyl_halide (418 words)

	biology - Hydrogen chloride
		The hydrogen chloride molecule HCl is a simple diatomic molecule consisting of a hydrogen atom H and a chlorine atom Cl connected with a covalent single bond.
		Joseph Priestley prepared pure hydrogen chloride in 1772, and in 1818 Humphry Davy proved it was chemically composed of hydrogen and chlorine.
		Historical uses of hydrogen chloride in the 20th century include hydrochlorinations of alkynes in producing the chlorinated monomers chloroprene and vinyl chloride, which are subsequently polymerized to make polychloroprene (Neoprene) and polyvinyl chloride (PVC), respectively.
	www.biologydaily.com /biology/HCl (1191 words)

	Carboxylic Acids
		The Acyl Halide Family is a family of organic compounds with the functional group being the -COX.
		Acyl Halides cannot be prepared from one of the members of the other acyl families because they represent the most reactive of the families.
		Acyl halides will react with water as a nucleophile to form the Carboxylic acid and a strong Hydrogen Halide whish will react with water itself to form a corrosive strong acid which can be very irritating to the eyes and skin.
	members.aol.com /profchm/acylhal.html (1220 words)

	First Reaction of a Bare Silicon Surface with Acid Chlorides and a One-Step Preparation of Acid Chloride Terminated ... (Site not responding. Last check: 2007-10-14)
		All compounds (butanoyl chloride (99+%), hexanoyl chloride (99+%), octanoyl chloride (99%), decanoyl chloride (98%), dodecanoyl chloride (98%), tetradecanoyl chloride (97%), hexadecanoyl chloride (98%), suberoyl chloride (97%), octylamine (99%), morpholine (99+%), and piperazine (99%) were purchased from Aldrich and used as received.
		The errors are the square roots of the sum of the variances of the yields from the octanoyl chloride and suberoyl chloride surfaces.
		To demonstrate the amine-reactivity of acid chloride terminated monolayers, patches of silicon were scribed under suberoyl chloride (ClCO(CH COCl) or octanoyl chloride (a control), washed with hexane, and then exposed for 24 h to 0.1 or 0.2 M solutions of octylamine, morpholine, and piperazine, and 10 ppm bovine serum albumin (BSA), all in DMSO.
	pubs.acs.org /cgi-bin/jcen?langd5/21/i06/html/la047338h.html (3510 words)

	Method for preparation of semipermeable composite membrane - Patent 4606943
		A substantial proportion of the acyl halide functional groups are hydrolyzed by the water present in the amine reagent as solvent, generating carboxylic acid groups or carboxylate salts.
		In addition, a polyacyl halide, such as trimesoyl chloride, or isophthaloyl chloride may be added to the reaction mixture of amine and anhydride to vary the properties of the resulting reverse osmosis membrane.
		The procedure of Example 1 was followed, however, to the triacyl chloride was added sufficient diacyl chloride in the form of isophathoyl chloride to achieve a ratio of (a) 7.5 to 1 and (b) 4.2 to 1.
	www.freepatentsonline.com /4606943.html (2685 words)

	home3
		The relative reactivity of acyl compounds toward nucleophilic substitution is:
		The behavior of acid chlorides and aldehydes in a reaction with a nucleophile is different because
		rather is converted to an acid chloride which is, in turn, reacted with an amine to give the amide.
	www2.latech.edu /~hji/org252/home3/home3.html (552 words)

	[No title] (Site not responding. Last check: 2007-10-14)
		Cellulose in natural or regenerated form may be modified by reacting it with an activated hydrophobic acyl group, such as an acid chloride or acid anhydride, in the presence of a hindered base, such as tripentylamine, to attach the acyl groups to the hydroxyls on the cellulose, to increase the hydrophobicity of the cellulose.
		Acetyl chloride Scheme II The methods disclosed herein are advantageous, because in the presence of the hindered base materials, such as cellulose materials, including cotton, may be covalently modified with hydrophobic groups, without degradation of the cellulose.
		The method of claim 3, wherein the activated acyl group is an acid chloride or acid anhydride, and wherein the method comprises covalently attaching the acyl group of the acid chloride or acid anhydride to hydroxyls on the cellulose, thereby to increase the hydrophobicity of the cellulose.
	www.wipo.int /cgi-pct/guest/getbykey5?KEY=99/49125.990930&ELEMENT_SET=DECL (8310 words)

	Carboxyl Derivative Reactivity
		The exceptional reactivity of acyl halides, on the other hand, facilitates their reduction under mild conditions, by using a poisoned palladium catalyst similar to that used for the partial reduction of alkynes to alkenes.
		Since acyl chlorides and anhydrides are expensive and time consuming to prepare, acids and esters are the most commonly used reactants for this transformation.
		Since acyl chlorides are more reactive than esters, isolation of the ketone intermediate formed in their reactions with organometallic reagents becomes an attractive possibility.
	www.cem.msu.edu /~reusch/VirtualText/crbacid2.htm (3912 words)

	Acids - 3 (Site not responding. Last check: 2007-10-14)
		Similar to acids and amides, the carbon atom of the acyl halide will be atom number 1 in the numbering scheme.
		Since it always occurs at the end of the chain of carbon atoms, the number is omitted.
		Acyl halides are man made, and the most commonly used is the acyl chloride.
	www.chem.ucalgary.ca /courses/351/Carey5th/nomenclature/acids/acids-3.html (102 words)

	Preparation of .alpha.-arylalkanoic acids - United States Patent 4,912,254
		By appropriate choice of the optical configuration of the substituted acyl halide, or the acyl amine or acid anhydride, in view of the single inversion during the rearrangement step, it is possible to produce a desired optically active.alpha.-acylalkanoic acid.
		The substituted acyl halides of formula II are prepared from corresponding acids by.alpha.-halogenation of the alkanoic acid by the addition of halide in the presence of a catalytic amount of phosphorus trichloride (Hell-Volhard-Zelinsky reaction) to afford the.alpha.-haloalkanoic acid.
		The optically active.alpha.-substituted acyl halides are prepared by resolution of the racemic.alpha.-hydroxyalkanoic acids or esters by conventional methods using optically active amine bases or from available amino acids, for example, such as by methods described in the Journal of the American Chemical Society, 76, 6054 (1954).
	xrint.com /patents/us/4912254 (11776 words)

	Carboxylic Acid Derivatives
		Phosphorus trichloride is the acid chloride of phosphorus acid.
		Phosphorus pentachloride is the acid chloride of phosphoric acid.
		Nucleophilic acyl substitution reaction of an acid chloride with the carboxylate anion is the most common.
	www.chem.latech.edu /~deddy/chem252/AcidDerAlphaSub.htm (1588 words)

	Nuffield Advanced Chemistry - Why is an acyl chloride, rather than a carboxylic acid, preferred in the condensation ...
		One is that the acyl chloride itself is a far more hazardous and volatile material to employ than the carboxylic acid, and, as you rightly point out, its use produces toxic HCl vapour.
		As you should know from the Nuffield course (Topic 15), acyl chlorides are far more reactive electrophiles than carboxylic acids, and their reactions can always be carried out under less vigorous conditions, often at room temperature.
		Providing that the acyl chloride is handled carefully and that the ensuing reaction is carried out in a fume cupboard, it is the preferred choice of reagent for the reasons given.
	www.chemistry-react.org /go/Faq/Faq_8897.html (361 words)

	WSU Projects (Site not responding. Last check: 2007-10-14)
		For example, acyl transfer from acyl chloride to amines produces amides in high yield in aprotic solvents.
		In water, however, amines are extensively solvated and are less reactive toward acyl chloride.
		Compared to acyl halides, methyl esters are markedly resistant to hydrolysis in water, but are reactive enough toward amines and other nulceophiles in aprotic solvents, and reside in the micellar interior as expected.
	www.webs.uidaho.edu /reuchem/wsu_projects.htm (1882 words)

	Chemistry 211 Experiment 7
		The best sythetic route from a carboxylic acid to an amide (and the one we will use) is to first convert the acid to the acid chloride, and react the acid chloride with the amine.
		Thionyl chloride and m-toluoyl (the acyl chloride derivative of m-toluic acid) chloride are corrosive and toxic.
		m-toluoyl chloride is a lachrymator--wear gloves while handling them, handle them only in the hood, and avoid breathing their vapors.
	www.miracosta.cc.ca.us /home/dlr/211exp7.htm (689 words)

	Derivative of kanamycin A and a process for the preparation thereof - Patent 4337336
		As the acylating agent, there may be used an acid chloride of a suitable carboxylic acid, particularly an alkanoic acid having 2-4 carbon atoms such as acetyl chloride and benzoyl chloride.
		C., benzoyl chloride (5.6 ml) was added to the solution and the reaction was conducted for 3 hours at 0.degree.-5.degree.
		Water (1 ml) was added to the reaction mixture to decompose the excess of benzoyl chloride, after which the reaction mixture was concentrated and poured into water (100 ml).
	www.freepatentsonline.com /4337336.html (2950 words)

	[No title]
		Thionyl chloride converts the carboxylic acid to the acyl chloride.
		This hindered hydride reagent adds only one H to an acyl chloride to produce an aldehyde as the product.
		A diorganocuprate reagent adds one alkyl group to an acyl chloride to produce a ketone.
	www.du.edu /~jhornbac/organic/oldexams/f98-1/q3pe1ans1.html (398 words)

	[No title] (Site not responding. Last check: 2007-10-14)
		The methylene acid ester group is then converted to the acid chloride and subsequently to its carboxamide, using the acid chloride and carboxamide formation steps that were described and shown above for the alpha-hydroxy acid group.
		In another two steps, compound 3 is converted into compound 4 with nucleophilic attack of cyanide ion on the chloride of the acyl chloride 3.
		Then, the acyl halide 3 is converted to a diazoketone 12 by nucleophilic attack of diazomethane on the acyl halide 3, as shown below.
	www.wipo.int /cgi-pct/guest/getbykey5?KEY=01/92249.011206&ELEMENT_SET=DECL (8501 words)

	Chem 130A Summer 2000 In-class Problem Set #3 Key (Site not responding. Last check: 2007-10-14)
		Nucleophilic acyl substitution of an amide is usually difficult because of the small amount of charge on the carbonyl carbon and a very poor leaving group.
		An ester has a greater charge on the carbonyl carbon and a better leaving group, so nucleophilic acyl substitution at an ester is faster than at an amide.
		An acyl chloride generally undergoes rapid nucleophilic acyl substitution because the charge on the carbonyl carbon is large and there is a reasonable leaving group.
	web.chem.ucla.edu /~harding/130A_su00_psd03_key.html (728 words)

	reaction between acyl chlorides and amines - addition / elimination (Site not responding. Last check: 2007-10-14)
		Ethanoyl chloride is taken as a typical acyl chloride.
		The first stage (the addition stage of the reaction) involves a nucleophilic attack on the fairly positive carbon atom by the lone pair on the nitrogen atom in the ethylamine.
		In the first, the carbon-oxygen double bond reforms and a chloride ion is pushed off.
	www.chemguide.co.uk /mechanisms/addelim/amines.html (333 words)

	reaction between acyl chlorides and ammonia - addition / elimination (Site not responding. Last check: 2007-10-14)
		This page gives you the facts and a simple, uncluttered mechanism for the nucleophilic addition / elimination reaction between acyl chlorides (acid chlorides) and ammonia.
		The first stage (the addition stage of the reaction) involves a nucleophilic attack on the fairly positive carbon atom by the lone pair on the nitrogen atom in the ammonia.
		It might be removed by a chloride ion, producing HCl (which would immediately react with excess ammonia to give ammonium chloride as above).
	www.chemguide.co.uk /mechanisms/addelim/ammonia.html (299 words)

	General Chemistry Online: Glossary: Introduction to organic chemistry
		A molecular fragment derived by removing a methyl hydrogen from propene (-CH For example, "allyl chloride" is 3-chloropropene, Cl-CH amide.
		For example, CH Cl is "methyl chloride" (systematic name: chloromethane); CH OH is "methyl alcohol" (systematic name: methanol).
		For example, ammonia and chloride ion are monodentate ligands of copper in the complexes [Cu(NH and [CuCl
	antoine.frostburg.edu /chem/senese/101/organic/glossary.shtml (1975 words)

	Reaction of Lithium Aluminum Hydride with Elemental Selenium: Its Application as a Selenating Reagent into Organic ... (Site not responding. Last check: 2007-10-14)
		Reaction of 2 with 2 equiv of acyl chloride gave diacyl selenide 3 in excellent yields.
		Reaction of N,N-diethyl amide and oxalyl chloride with 2 gave N,N-diethyl selenoamide 7 in 68% yield.
		N,N-Dimethyl selenocarbamoyl chloride (CH NC(=Se)Cl is easily prepared in situ from reaction of 2 with dichloromethylenedimethyliminium chloride [Cl ]Cl and can be trapped with various nucleophiles such as amines, lithium alkylthiolates, and lithium alkylselenolates, to give the corresponding selenoureas 10, S-alkyl selenothiocarbamates 11, and Se-alkyl diselenocarbamates 12 in good to high yields.
	pubs.acs.org /cgi-bin/jcen?jacsat/123/i34/html/ja005800o.html (1436 words)

	June Posts: SS: Re: C1s chemical shift for an acyl chloride gro
		SS: Re: C1s chemical shift for an acyl chloride group
		In reply to: Matt Linford: "SS: C1s chemical shift for an acyl chloride group"
		Thus, it seems reasonable that the carbon in the acyl chloride
	www.uwo.ca /ssw/archives/2002/jun02/0031.html (319 words)

	Professor Ronald E. Hess's Research Interests (Site not responding. Last check: 2007-10-14)
		To the present time, our interest has been in the synthesis and characterization of selected aldoketene dimers and trimers and in the mechanisms of their formation.
		The synthesis we employ is the well-known base-promoted dehydrohalogenation of an acyl chloride in an appropriate solvent, such as diethyl ether or methylene chloride, generally at reflux temperatures.
		For example, reactions of propionyl chloride, butyryl chloride, and valeryl chloride with NEt3 produce methylketene, ethylketene, and n-propylketene, respectively.
	webpages.ursinus.edu /chemistry/ronres.html (407 words)

	243april23.html
		Acyl chloride reduced to alcohol, stopped at aldehyde with partially deactivated Pd.
		Sterically bulky hydrides reduce esters and acyl chlorides to aldehydes.
		A. H2CrO4 (CrO3 or Na2Cr2O7 in aqueous acid) most commonly used to oxidize 1o alcohol to carboxylic acid and 2o alcohol to ketone.
	spot.pcc.edu /~chandy/243/243april23.html (418 words)

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