stereospecificadj.
/ˌstɛrɪəʊspᵻˈsɪfɪk/, /ˌstɪərɪəʊspᵻˈsɪfɪk/, U.S. /ˌstɛriəspəˈsɪfɪk/ Chemistry.
1.
a. Of a reaction: = stereoselective adj. Also of a catalyst: causing a reaction to be (more) stereoselective.
ΘΚΠ
the world > matter > chemistry > chemical reactions or processes > [adjective] > of or relating to that which affects reaction > of or relating to catalysis > of or relating to stereospecific catalysts
stereospecific1949
1949 Jrnl. Amer. Chem. Soc. 71 3866/2 The reaction giving rise to the acetates was at least 90% stereospecific since the ratio of the yield of the acid phthalate of racemate I to the yield of the acid phthalates of other alcohols was ten to one. Stereospecificity of even a higher degree was found in the II series.
1957 Chem. Abstr. 51 15993 [Abstract of art. by G. Natta et al. in 1957 Gazz. Chim. Ital. LXXXVII] Stereospecific polymerization... First syntheses of isotactic and atactic polypropene.
1958 Chem. Abstr. 52 1106 (heading) Isotactic and other stereospecific polymers.
1959 Times Rev. Industry Feb. 57/1 Using the stereospecific catalysts developed in Germany by K. Ziegler, Professor Natta in Milan had succeeded in producing, from propylene gas, useful polymers which he characterized as isotactic.
1960 Times 19 July (Royal Soc. Tercentenary Suppl.) p. xiv/3 The past decade has seen the emergence of various stereospecific syntheses.
1966 Petroleum Handbk. (ed. 5) 215/2 There are two possibilities in building up the polymer chain [of propylene]; the methyl groups can be situated either at random on both sides of the chain or on one side of the chain only (stereospecific polymerization).
1968 I. L. Finar Org. Chem. (ed. 4) II. iv. 126 The term stereospecific reaction has been used in the same sense as stereoselective reaction, but now the tendency is to restrict the use of stereospecific to a reaction in which different stereoisomers produce different products or act at different rates.
1978 J. A. Brydson Rubber Chem. i. 8 Stereospecific catalyst systems..led to the availability of..rubbers with a much more controlled molecular architecture than had been obtained before.
1979 Jrnl. Org. Chem. 44 3374 The determination of the configuration at C-24 of the revised structure of oogoniol..was accomplished by the stereospecific synthesis of the model compounds..which contain the oogoniol side chain.
b. Of a polymer, esp. rubber: = stereoregular adj.
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the world > matter > chemistry > polymer chemistry > polymers > [adjective] > stereochemical properties
volumeless1946
isotactic1955
syndiotactic1956
stereoregular1959
stereoregulated1959
stereoregulating1959
stereospecific1959
1959 Times 27 Apr. (Rubber Industry Suppl.) p. ii/7 Polymer chemists have long yearned to synthetize such stereo-specific polymers found to occur so prevalently in Nature.
1961 Industr. Chemist Feb. 74/2 Although stereoregular polymers prepared with Ziegler-type catalysts are now of considerable commercial interest, research is continuing in attempts to obtain stereo-specific polymers by other, and perhaps less complex, catalysts.
1966 Petroleum Handbk. (ed. 5) 224/1 In the last few years..a new family of synthetic rubbers—the stereospecific rubbers—have been developed.
1974 J. Ford-Smith tr. Heinisch Dict. Rubber 447/1 Examples of stereospecific polymers are cis-1:4-polyisoprene and cis-1:4-polybutadiene.
2. Of a reaction or process: yielding a product, or having a rate, that depends on the particular stereoisomeric form of the starting material.
ΘΚΠ
the world > matter > chemistry > isomerism > [adjective] > of or relating to stereo-isomerism > stereospecific
stereospecific1959
1959 Jrnl. Amer. Chem. Soc. 81 110/1 A stereospecific process is one in which the configuration of the product is related to that of the reactant... A stereoselective process is one in which there is no relationship between the configuration of the reactant and that of product but one in which there is a definite driving force for forming one of the possible stereoisomeric products.
1962 E. L. Eliel Stereochem. Carbon Compounds xv. 436 All stereospecific processes are stereoselective, but not all stereoselective processes are stereospecific. For example, the low-temperature free-radical addition of hydrogen bromide to the 2-bromo-2-butenes..is both stereospecific and stereo~selective in that the cis olefin gives meso-2,3-dibromobutane whereas the trans olefin gives the dl-dibromide. At higher temperature the reaction is still stereoselective (formation of 75% dl isomer to 25% meso isomer) but no longer stereospecific; both olefins now give the same product mixture.
1968 I. L. Finar Org. Chem. (ed. 4) II. iv. 126 The term stereospecific reaction has been used in the same sense as stereoselective reaction, but now the tendency is to restrict the use of stereospecific to a reaction in which different stereoisomers produce different products or act at different rates.
1970 J. H. Quastel in Ehrenpreis & Solnitsky Neurosci. Res. III. 15 Stereospecific effects are also observed in cerebral amino acid exchange reactions; for example, elevated cerebral L-lysine is more effective than elevated cerebral D-lysine in increasing L-lysine exchange.
1978 Biochem. Pharmacol. XXVII. 653/1 The finding that the R-enantiomer of gliflumide binds less strongly [than the S-enantiomer] indicates that antidiabetic drugs are bound to plasma by a stereospecific process.
Derivatives
ˌstereospeˈcifically adv. in a stereospecific manner.
ΘΚΠ
the world > matter > chemistry > isomerism > [adverb] > specifically by stereoisomerism > stereospecifically
stereospecifically1955
1955 Jrnl. Amer. Chem. Soc. 77 4567/1 cis-Propenyllithium prepared from cis-2-bromopropene with lithium in ether..reacts stereospecifically with benzaldehyde..to give..the alcohol with the same configuration as that of the starting bromide.
1965 C. S. G. Phillips & R. J. P. Williams Inorg. Chem. I. x. 383 Other monomers can be stereo-specifically polymerized.
1979 Jrnl. Chem. Soc.: Chem. Comm. 920/2 The oxidative cycloaddition constitutes a method for the formation, stereospecifically, and in a single step, of four chiral centres from an archiral, acyclic reactant.
ˌstereospeciˈficity n. the property or state of being stereospecific.
ΘΚΠ
the world > matter > chemistry > isomerism > [noun] > stereo-isomerism > stereospecificity
stereospecificity1949
1949 Jrnl. Amer. Chem. Soc. 71 3866/2 The reaction giving rise to the acetates was at least 90% stereospecific since the ratio of the yield of the acid phthalate of racemate I to the yield of the acid phthalates of other alcohols was ten to one. Stereospecificity of even a higher degree was found in the II series.
1970 Jrnl. Polymer Sci. A. 8 988 The stereospecificity of these catalysts is remarkable since they yield polybutadienes with a very high 1,4 content.
1970 J. H. Quastel in Ehrenpreis & Solnitsky Neurosci. Res. III. 15 Studies of the stereospecificity of amino acid uptake in vivo have shown..that the l-amino acid usually penetrates the brain to a greater extent than the corresponding d-isomer.
1979 Jrnl. Chem. Soc.: Chem. Comm. 918/2 Oxidation of labelled hexa-1, 5-dienes with permanganate generages four new chiral centres with complete stereospecificity.
This entry has not yet been fully updated (first published 1986; most recently modified version published online March 2022).
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adj.1949