alkyln.
/ˈalkʌɪl/, /ˈalkɪl/, U.S. /ˈælˌkɪl/, /ˈælk(ə)l/ Chemistry.
1. Any of the series of hydrocarbon groups or radicals derived from alkanes by the removal of a hydrogen atom, as methyl (—CH3), ethyl (—C2H5), propyl (—C3H7), etc. Cf. aryl n.Recorded earliest as a formative element in compound names.
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alkyl1879
ethanediol1897
1879 Jrnl. Chem. Soc. 36 522 (title) Boiling points of the ethereal salts of hydroxy- and alkyloxy-acids.
1896 Jrnl. Amer. Chem. Soc. 18 32 It is easier to form a primary amine or ammonium salt of a tertiary alkyl than it is to form a pyridinium salt of the same alkyl.
1906 G. M'Gowan & J. J. Sudborough Bernthsen's Text-bk. Org. Chem. 22 The monovalent residues, CnH2n+1 (methyl, ethyl, etc.),..are frequently termed alkyls.
1977 J. March Adv. Org. Chem. (ed. 2) v. 183 Alkylcarbenes can undergo rearrangement, with migration of alkyl or hydrogen.
1987 A. Nickon & E. F. Silversmith Org. Chem.: Name Game xiii. 163 All four N-methyl groups need to be there to make 1 an effective sponge; with fewer alkyls the diamines are far less potent.
2. A compound containing one or more alkyl groups bonded to a distinctive atom, esp. a metal. Chiefly with distinguishing word. Cf. Compounds 1b.
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1889 G. M'Gowan tr. A. Bernthsen Text-bk. Org. Chem. 37 The halogen alkyls, CnH2n+1X.
1909 E. I. Lewis Elements Org. Chem. v. 48 Magnesium, in somewhat similar circumstances, forms a compound which is not spontaneously inflammable and which is easily prepared. It is more reactive than the zinc alkyls.
1968 Brit. Jrnl. Plastic Surg. 21 339 All petrol nowadays contains lead alkyls (tetraethyl and tetramethyl lead) in a concentration of one part of lead alkyl to 1,300 parts of petrol.
1981 P. Sykes Guidebk. to Mechanism in Org. Chem. (ed. 5) x. 283 It is also possible, under suitable conditions, to generate the alkyls of more electropositive metals, e.g. sodium.
2000 C. A. Russell in F. L. Holmes & T. H. Levere Instruments & Exper. Hist. Chem. xii. 315 The wholly unexpected discovery of the remarkable zinc alkyls.
Compounds
C1.
a. attributive or as a formative element in names of types of compounds.
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1879Alkyloxy-acids [see sense 1].
1882 Jrnl. Chem. Soc. 42 831 (title) Synthesis of so-called alkyl disulphoxides.
1909 E. I. Lewis Elements Org. Chem. xviii. 154 When a mixture of phenyl bromide and an alkyl bromide is treated with sodium, the reaction takes place more readily, with the production of the alkyl-benzene.
1953 Sci. News 30 91 One of the detergents..is an alkyl sulphate, with an average chain-length of about eight to ten carbon atoms.
1974 M. C. Gerald Pharmacol. vii. 133 Chemically, these agents are organic alkylphosphate esters, which are called simply organophosphates.
1989 Nature 23 Feb. 722/1 They correlate in the sedimentary record with other domestic surfactant markers, such as the long-chain alkylbenzenes.
2003 Corrosion Sci. 45 1703 Carboxylating requires use of both n-alkyl carboxylic acid and peroxoborate as oxidizing agent.
b. With names of metals, denoting compounds in which one or more alkyl groups are bonded directly to a metal atom, as alkyllead, alkyllithium, alkylmercury, etc. Cf. sense 2.
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1907 Jrnl. Amer. Chem. Soc. 29 96 Tschelinzew's results show that the Grignard reaction goes in two phases: 1. formation of the alkyl magnesium salt; 2. union of this with the ether.
1939 Science 10 Nov. 434/1 R and R′ are the groups to be redistributed, M is the carrier, such as Pb in the case of alkyllead compounds.
1944 U.S. Patent 2,361,337 1/1 Gasoline-type fuels containing added alkyl lead in sufficient quantity materially to reduce their storage stability.
1970 Environmental Sci. & Technol. 4 892/3 To control contamination, D'Itri sees two approaches—regulating all forms of mercury and controlling strictly the alkyl mercuries.
1987 A. Nickon & E. F. Silversmith Org. Chem. xviii. 253 They converted..acetaldehyde to the 2-methyl-1, 3-dithiane and then removed a proton with alkyllithium.
1998 Environmental Health Perspectives 106 116/3 The search for suitable antiknock agents has resulted in the development of alkyl leads (tetramethyl and tetraethyl lead) as cost-effective octane enhancers.
C2. General attributive, as alkyl group, alkyl radical, etc.
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alkyl1922
1883 Jrnl. Chem. Soc. 44 919 Action of the Alkyl-derivatives of the Halogen-substituted Fatty Acids on Aniline.
1899 E. F. Smith tr. R. Anschütz V. von Richter's Org. Chem. (ed. 3) I. iv. 399 Nitroso-ureas are formed when nitrites act upon nitrates or sulphates of ureas which contain an alkyl group in the amido group.
1922 J. J. Sudborough Bernthsen's Text-bk. Org. Chem. (new ed.) iv. 107 By the introduction of alkyl radicals in place of hydrogen into the ammonia molecule, the important class of ammonia bases or amines is formed.
1981 J. W. Buttle et al. Chem. (ed. 4) xviii. 396 The hydrocarbon residue is referred to as the alkyl group..if derived from an aliphatic hydrocarbon.
1999 Oil & Gas Jrnl. (Nexis) 7 June 55 In cat gasoline, approximately 60% of sulfur compounds are thiophenes and their alkyl derivatives.
C3.
alkyl halide n. any compound whose molecule consists of an alkyl group bonded to one or more halogen atoms; = haloalkane n. at halo- comb. form2 2.
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1898 Philos. Trans. 1897 (Royal. Soc.) A. 190 104 The condensation of alcohol with alkyl halides in the presence of an alcoholate.
1964 P. J. Hills Small Scale Org. Prepar. iv. 34 The hydrolysis of an alkyl halide. When boiled with an aqueous alkali, both ethyl bromide and ethyl iodide are converted to ethyl alcohol.
2000 M. Clugston & R. Flemming Adv. Chem. xxiv. 436 The alkyl halides and alicyclic halides have similar properties, which are distinctly different from those of the aryl halides.
This entry has been updated (OED Third Edition, September 2009; most recently modified version published online December 2021).
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