Tracing the origins and evolution of chirality and handedness in chemical language

Angewandte Chemie - International Edition

Volumn 46, Issue 22, 2007, Pages 4016-4024

  Cintas, Pedro ^a  

^a UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

Chemical semiology; Chirality; Handedness; History of science; Stereochemistry

Indexed keywords

SEMANTICS; STEREOCHEMISTRY; SYNTACTICS;

CHEMICAL LANGUAGE; CHEMICAL SEMIOLOGY; HANDEDNESS;

CHIRALITY;

EID: 34250691471     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603714     Document Type: Review

References (91)

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23. for dextro-and levorotatory quartz, pp. 262-263), while this behavior of some natural liquids or solutions of solids (oil of turpentine, oil of lemon, camphor in alcohol, sugar in water) seems to be a property of individual molecules ("Phénomènes de polarisation successive, observès dans les fluides homogènes": J.-B. Biot, Bull. Soc. Philomath. Paris 1815, 190-192).
24. Later, he advanced a "molecular" explanation, although the term molecule by that time should be interpreted in a broad, flexible sense, related to Newton's corpuscular theory: "the phenomenon] being a property of molecules regardless of their state of aggregation" ("... une faculté propre à ces molécules indépendamment de leur état d'agrégation"; "Mémoire sur les rotations que certaines substances impriment aux axes de polarisation des rayons lumineux": J.-B. Biot, Mem. Acad. Sci. lnst. Fr. 1817, 2, 41-136).
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26. P. Ball, Elegant Solutions. Ten Beautiful Experiments in Chemistry, Royal Society of Chemistry, Cambridge, 2005, pp. 101-118. This remarkable discovery has been described in later hagiographies of Pasteur with a certain eureka-like style, but it probably did not occur in the same way.
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38. By the late 1860s it was known that lactic acid from sour milk was optically inactive, while the so-called sarcolactic acid from muscle tissue, which has similar properties, was optically active. No chemical resolution of milk lactic acid was attempted, and therefore it was never determined whether an enantiomer of sarcolactic acid might be present in milk. See O. B. Ramsay, Stereochemistry, Heyden, London, 1981, pp. 78-80.
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46. For a historical perspective: E. L. Eliel, Abstracts of Papers, 230th National Meeting of the American Chemical Society, Washington, DC, 2005, HIST9.
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49. b) L. L. Whyte, Nature 1958, 182, 198;
50. c) there is also an interesting posthumous paper: Leonardo 1975, 8, 245-248.
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53. Chiral borromeates have been prepared recently, and one enantiomeric compound was isolated in the solid state: C. D. Pentecost, A. J. Peters, K. S. Chichak, G. W. V. Cave, S. J. Cantrill, J. F. Stoddart, Angew. Chem. 2006, 118, 4205-4210;
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55. Molecular deformations in some vibrational states will impart chirality to a molecule of methane and, as a result, at any time, individual molecules will almost always be chiral. The cancellation of two exactly mirror-image structures may only be asserted on a statistical basis; see Ref. [16] and especially the discussion on pp. 22-26.
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66. In a broad sense asymmetric (or asymmetrical) means lacking symmetry, mis-proportionated, or simply unequal. The latter is the common use of asymmetry in biological sciences: not equal in quantity, size, rank, value, etc. (see Section 6 of this essay). In physics, the terms asymmetric, antisymmetric, and nonsymmetric as applied to wave functions follow the sense attributed in logic, that is, a relation never holding between a pair of values x and y when it holds between y and x.
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