A web site for calculating the degree of chirality

Chirality

Volumn 23, Issue 1, 2011, Pages 17-23

  Zayit, Amir ^a   Pinsky, Mark ^a   Elgavi, Hadassah ^a   Dryzun, Chaim ^a   Avnir, David ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

asymmetry; CCM; chirality; CSM; internet; inversion symmetry; mirror symmetry; S n symmetry; web site

Indexed keywords

CALCULATION; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; GEOMETRY; MOLECULE; PRIORITY JOURNAL; REVIEW; WEB BROWSER;

EID: 78650030204     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20807     Document Type: Review

References (54)

1. Shubnikov AV, Koptsik VA,. Symmetry in science and art. New York: Plenum Press; 1997. p 420.
2. Hargittai M, Hargittai I,. Symmetry through the eyes of a chemist. New York: Springer, 3nd ed., 1995. 520 p.
3. Kettle SFA,. Symmetry and structure, 2nd ed. Chichester: Wiley; 1995. p 415.
4. Derry GN,. What science is and how it works, Chapter 18: Riding Blake's tiger: symmetry in science, art and mathematics. New Jersey, Princeton University press; 2002. p 252-270.
5. Atkins P,. Galileo's finger: The ten great ideas of science, Chapter 6: Symmetry-the quantification of beauty. New York: Oxford University Press; 2003. p 163-200.
6. Livio M,. The equation that couldn't be solved: how mathematical genius discovered the language of symmetry. New York: Simon & Schuster; 2005. p 368.
7. Hartley RI,. Chirality. Inter J Comp Vision 1998; 26: 41-61.
8. Forsman A, Merilaita A,. Fearful symmetry? Intra-individual comparisons of asymmetry in cryptic vs. signalling colour patterns in butterflies. Evol Ecol 2003; 17: 491-507.
9. Palmer SE, Hemenway K,. Orientation and symmetry: effects of multiple, rotational and near symmetries. J Exp Psychol Hum Percept Perform 1978; 4: 691-702.
10. Brunner H,. Chirality and art-ropes and twisted strings in paintings. Enantiomer 2001; 5: 545-547.
11. Cintas P,. Tracing the origins and evolution of chirality and handedness in chemical language. Angew Chem Int Ed 2007; 46: 4016-4024.
12. Bentley R,. Chiral: A confusing etymology. Chirality 2009; DOI 10.1002/CHIR.20699.
13. Morrison RT, Boyd RN,. Organic chemistry, 6th ed. New Jersey: Prentic Hall, Englewood Cliffs; 1992. p 443-487.
14. Kalsi PS,. Stereochemistry conformation and mechanism, 6th ed. Wiley Eastern Ltd; 1990. p 490-495.
15. Goldberg SI, Lam FL, Sahli MS,. Differentiation of cis- and trans-4-substituted-1-methylcyclohexanes by their NMR. signal envelopes. J Chem Eng Data 1969; 4: 406-408.
16. Shrivastava RK, Maudru E, Singh G, Wightman RH, Morgan KM,. Synthesis of chiral cyclohexanes and carbasugars by 6-exo-dig radical cyclisation reactions. Beilstein J Org Chem 2008; 4: 43-50.
17. Lipkowitz KB, Schefzick S, Avnir D,. Enhancement of enantiomeric excess by ligand distortion. J Am Chem Soc 2001; 123: 6710-6711.
18. Alvarez S, Schefzick S, Lipkowitz K, Avnir D,. Quantitative chirality analysis of molecular subunits of bis(oxazoline)copper(ii) complexes in relation to their enantioselective catalytic activity. Chem Eur J 2003; 9: 5832-5837.
19. Katzenelson O, Avnir D,. Quantitative chirality/enantioselectivity relations in large random supramolecular structures. Chem Euro J 2000; 6: 1346-1354.
20. Yogev-einot D, Avnir D,. The temperature-dependent optical activity of quartz: from Le Chatelier to chirality measures. Tetrahedron: Asymmetry 2006; 17: 2723-2725.
21. Keinan S, Avnir D,. Quantitative chirality in structure-activity correlations. Shape recognition by trypsin, by the D2 dopamine receptor and by cholinesterases. J Am Chem Soc 1998; 120: 6152-6159.
22. Pinto Y, Salomon Y, Avnir D,. Properties and classification of enantiomerization pathways. J Math Chem 1998; 23: 13-29. (Pubitemid 128367548)
23. Malek K, Jansen APJ, Li C, van Santen RA,. Enantioselectivity of immobilized Mn-salen complexes: a computational study. J Catal 2007; 246: 127-135.
24. Yogev-einot D, Avnir D,. Pressure and temperature effects on the degree of symmetry and chirality of the molecular building blocks of low quartz. Acta Cryst 2004; B60: 163-173.
25. Buda AB, der Heyde TA, Mislow K,. On quantifying chirality. Angew Chem Int Ed Engl 1992; 31: 989-1007.
26. Gilat G,. On quantifying chirality-Obstacles and problems towards unification. J Math Chem 1994; 15: 197-205.
27. Weinberg N, Mislow K,. A Unification of Chirality Measures. J Math Chem 1995; 17: 35-53.
28. Mezey PG,. Quantum similarity measures and Löwdin's transform for approximate density matrices and macromolecular forces. Inter J Quant Chem 1997; 63: 39-48.
29. Mezey PG,. The holographic electron density theorem and quantum similarity measures. Mol Phys 1999; 96: 169-178.
30. Garzón IL, Reyes-Nava JA, Rodríguez-Hernández JI, Sigal I, Beltrán MR, Michaelian K,. Chirality in bare and passivated gold nanoclusters. Phys Rev B 66: 073403, 2002.
31. Petitjean M,. Chirality and symmetry measures: A transdisciplinary review. Entropy 2003; 5: 271-312.
32. Mili IS, Sorensen DC,. A symmetry preserving singular value decomposition. Siam J Matrix Anal Appl C 2006; 28: 749-769.
33. Milner D, Raz S, Hel-Or H, Keren D, Nevo E,. A new measure of symmetry and its application to classification of bifurcating structures. Pattern Recog 2007; 40: 2237-2250.
34. Pietropaolo A, Muccioli L, Berardi R, Zannoni C,. A chirality index for identifying protein secondary structures. Protein Struct Funct Bioinfo 2008; 70: 667-677.
35. Zabrodsky H, Peleg S, Avnir D,. Continuous symmetry measures. J Am Chem Soc 1992; 114: 7843-7851.
36. Pinsky M, Dryzun C, Casanova D, Alemany P, Avnir D,. Analytical methods for calculating continuous symmetry measures and the chirality measure. J Comp Chem 2008; 29: 2712-2721.
37. Zabrodsky H, Avnir D,. Continuous symmetry measures, IV: chirality. J Am Chem Soc 1995; 117: 462-473.
38. Dryzun C, Mastai Y, Shvalb A, Avnir D,. Chiral silicate zeolites. J Mater Chem 2009; 19: 2062-2069.
39. For a list of publications, Prof. David Avnir's home page. Available at
40. Pinto Y, Fowler PW, Mitchell D, Avnir D,. Continuous chirality analysis of model stone-wales rearrangements in fullerenes. J Phys Chem 1998; 102: 5776-5784.
41. Alvarez S, Pinsky M, Llunell M, Avnir D,. Continuous chirality analysis of hexacoordinated tris-chelated metal complexes. Crystal Eng 2001; 4: 179-200. (Pubitemid 32544543)
42. Alemany P, Alvarez S, Avnir D,. Theoretical evidence of persistent chirality in D3 homoleptic hexacoordinated complexes with monodentate ligands. Chemistry-Europ J 2003; 9: 1952-1957.
43. Handgraaf JW, Reek JNH, Bellarosa L, Zerbetto F,. Continuous chirality measure in reaction pathways of ruthenium-catalyzed transfer hydrogenation of ketones. Adv Synth Catal 2005; 347: 792-802.
44. Wei Y, Sastry GN, Zipse H,. Org Lett 2008; 10: 5413-5416.
45. Bellarosa L, Zerbetto FJ,. Enantiomeric excesses and electronic chirality measure. J Am Chem Soc 2003; 125: 1975-1979.
46. Grimme S,. Continuous symmetry measures for electronic wavefunctions. Chem Phys Lett 1998; 297: 15-22.
47. Pinsky M, Avnir D,. Continuous symmetry measures, V: the classical polyhedra. Inorg Chem 1998; 37: 5575-5582.
48. Pinsky M, Yogev-Einot D, Avnir D,. Statistical analysis of the estimation of distance measures. J Comput Chem 2003; 24: 786-796.
49. Jmol: an open-source Java viewer for chemical structures in 3D. Available at
50. The Open Babel Package, version 2.0.0. Available at:. Accessed on Dec 1, 2005.
51. Guha R, Howard MT, Hutchison GR, Murray-Rust P, Rzepa H, Steinbeck C, Wegner J, Willighagen EL,. The blue obelisk interoperability in chemical informatics. J Chem Inf Model 2006; 46: 991-998.
52. Tilley RJD,. Crystals and crystal structures. New-York: Wiley; 2006. p 270.
53. Alvarez S, Avnir D, Llunell M, Pinsky M,. Continuous symmetry maps and shape classification. the case of six-coordinated metal compounds. New J Chem 2002; 26: 996-1009.
54. Llunell M, Casanova D, Cirera J, Bofill JM, Alemany P, Alvarez S, Pinsky M, Avnir D,. SHAPE program (version 1.1). Barcelona 2003.