Vibrational and electronic circular dichroism of Δ-TRISPHAT [tris(tetrachlorobenzenediolato)-phosphate(V)] anion

Chirality

Volumn 17, Issue SUPPL., 2005, Pages

  Bas, Delphine ^a   Bürgi, Thomas ^b   Lacour, Jérôme ^a   Vachon, Jérôme ^a   Weber, Jacques ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b UNIVERSITÉ DE NEUCHÂTEL   (Switzerland)

Author keywords

TRISPHAT anion; CD properties; DFT; VCD; X ray crystallography

Indexed keywords

ANION; CINCHONIDINE; PHOSPHATE; TRIS(TETRACHLOROBENZENEDIOLATO)PHOSPHATE; UNCLASSIFIED DRUG;

CALCULATION; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONFERENCE PAPER; DENSITY FUNCTIONAL THEORY; ELECTRONIC CIRCULAR DICHROISM; INFRARED RADIATION; PRIORITY JOURNAL; VIBRATIONAL CIRCULAR DICHROISM; X RAY CRYSTALLOGRAPHY;

EID: 21844478737     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20131     Document Type: Conference Paper

References (62)

1. Lacour J, Hebbe-Viton V. Recent developments in chiral anion mediated asymmetric chemistry. Chem Soc Rev 2003;32:373-382.
2. Llewellyn DB, Arndtsen BA. The use of a chiral borate counteranion as a H-1 NMR shift reagent for cationic copper(I) complexes. Can J Chem 2003;81(11):1280-1284.
3. Carter C, Fletcher S, Nelson A. Towards phase-transfer catalysts with a chiral anion: inducing asymmetry in the reactions of cations. Tetrahedron: Asymmetry 2003;14(14):1995-2004.
4. Llewellyn DB, Arndtsen BA. Design, synthesis, and characterization of a new class of amino acid-based chiral borate counteranions. Organometallics 2004;23(12):2838-2840.
5. Lacour J, Ginglinger C, Grivet C, Bernardinelli G. Synthesis and resolution of the configurationally stable tris (tetrachlorobenzenediolato) phosphate anion. Angew Chem Int Ed Engl 1997;36(6):608-609.
6. Lacour J, Ginglinger C, Favarger F, Torche-Haldimann S. Application of TRISPHAT anion as NMR chiral shift reagent. Chem Commun 1997(23):2285-2286.
7. 31P NMR determination of the enantiomeric purity of quaternary phosphonium cations using TRISPHAT as chiral shift agent. Tetrahedron Lett 1998;39(41):7495-7498.
8. 4N][Δ- TRISPHAT] salt. Efficient NMR chiral shift reagent for neutral planar chiral tricarbonyl chromium complexes. Organometallics 2000;19(19):3997-3999.
9. Giner Planas J, Prim D, Rose-Munch F, Rose E, Monchaud D, Lacour J. TRISPHAT anion. An efficient NMR chiral shift counter-ion for planar chiral cationic tricarbonyl manganese complexes. Organometallics 2001;20:4107-4110.
10. Maury O, Lacour J, Le Bozec H. Diastereoselective homochiral self-assembly between anions and cation in solution. Eur J Inorg Chem 2001:201-204.
11. 2 and its differentiation by the TRISPHAT anion. Organometallics 2001;20(10):1904-1906.
12. Lacour J, Vial L, Bernardinelli G. One-step stereoselective synthesis and NMR chiral shift properties of a novel hexacoordinated phosphorus cation. Org Lett 2002;4(14):2309-2312.
13. Pasquato L, Herse C, Lacour J. NMR enantiodifferentiation of thiiranium cations by BINPHAT and TRISPHAT chiral anions. Tetrahedron Lett 2002;43(32):5517-5520.
14. Vial L, Lacour J. Conformational preference and configurational control of highly symmetric spirobi[dibenzazepinium] cation. Org Lett 2002;4(22):3939-3942.
15. Amouri H, Thouvenot R, Gruselle M. Differentiation of planar chiral enantiomers of [Cp*M(2-alkyl-Phenoxo)][BF4] {M = Rh, Ir} by the TRISPHAT anion. CR Chim 2002;5(4):257-262.
16. 6-phenyl) chromium]pyridine. Chem Commun 2003:658-659.
17. 6-arene)chromium complexes. Organometallics 2003;22(25):5243-5260.
18. 2 symmetry using the TRISPHAT anion and a lanthanide shift reagent. New J Chem 2003;27:748-751.
19. Desvergnes-Breuil V, Hebbe V, Dietrich-Buchecker C, Sauvage J-P, Lacour J. NMR evaluation of the configurational stability of Cu(I) complexes. Inorg Chem 2003;42:255-257.
20. Hebbe V, Londez A, Goujon-Ginglinger C, Meyer F, Uziel J, Jugé S, Lacour J. NMR enantiodifferentiation of triphenylphosphonium salts by chiral hexacoordinated phosphate anions. Tetrahedron Lett 2003; 44(12):2467-2471.
21. 3 symmetric cyclic hexapeptides. Chem Commun 2003:1252-1253.
22. Caspar R, Amouri H, Gruselle M, Cordier C, Malezieux B, Duval R, Leveque H. Efficient asymmetric synthesis of Δ- and Λ-enantiomers of (bipyridyl)ruthenium complexes and crystallographic analysis of Δ-bis(2,2′-bipyridine)(2,2′-bipyridine-4,4′- dicarboxylato)ruthenium: diastereoselective homo- and heterochiral ion pairing revisited. Fur J Inorg Chem 2003(3):499-505.
23. Hiraoka S, Harano K, Tanaka T, Shiro M, Shionoya M. Quantitative formation of sandwich-shaped trinuclear silver (I) complexes and dynamic nature of their P⇌M flip motion in solution. Angew Chem Int Ed 2003;42(42):5182-5185.
24. 31P PGSE NMR diffusion studies on chiral organic salts: ion pairing and the dependence of a diffusion value on diastereomeric structure. Chem Eur J 2004;10(12):2912-2918.
25. Jodry JJ, Mikami K. New chiral imidazolium ionic liquids: 3D network of hydrogen bonding. Tetrahedron Lett 2004;45(23):4429-4431.
26. Lacour J, Torche-Haldimann S, Jodry JJ, Ginglinger C, Favarger F. Ion pair chromatographic resolution of tris (diimine) ruthenium(II) complexes using TRISPHAT anions as resolving agent. Chem Commun 1998:1733-1734.
27. Lacour J, Goujon-Ginglinger C, Torche-Haldimann S, Jodry JJ. Efficient enantioselective extraction of tris(diimine)ruthenium(II) complexes by chiral lipophilic TRISPHAT anions. Angew Chem Int Ed 2000;39:3695-3697.
28. Jodry JJ, Lacour J. Efficient resolution of dinuclear triple helicate by asymmetric extraction/precipitation using TRISPHAT anions as resolving agents. Chem Eur J 2000;6(23):4297-4304.
29. Monchaud D, Lacour J, Coudret C, Fraysse S. TRISPHAT salts. Efficient NMR chiral shift and resolving agents for substituted cyclometallated ruthenium bis(diimine) complexes. J Organomet Chem 2001;624(1-2):388-391.
30. Chavarot M, Menage S, Hamelin O, Charnay F, Pecaut J, Fontecave M. "Chiral-at-metal" octahedral ruthenium(II) complexes with achiral ligands: a new type of enantioselective catalyst. Inorg Chem 2003; 42(16):4810-4816.
31. 6. Inorg Chem 2003; 42(4):1378-1385.
32. Hamelin O, Pecaut J, Fontecave M. Crystallization-induced asymmetric transformation of chiral-at-metal ruthenium (II) complexes bearing achiral ligands. Chem Eur J 2004;10(10):2548-2554.
33. Lacour J, Jodry JJ, Ginglinger C, Torche-Haldimann S. Diastereoselective ion pairing of TRISPHAT anions and tris(4,4′-dimethyl-bipyridine)iron(II) complex. Angew Chem Int Ed Engl 1998;37(17): 2379-2380.
34. Lacour J, Jodry JJ, Monchaud D. Configurational ordering of a cationic dinuclear triple helicate by chiral TRISPHAT anions. Chem Commun 2001:2302-2303.
35. Monchaud D, Jodry JJ, Pomeranc D, Heitz V, Chambron J-C, Sauvage J-P, Lacour J. Ion-pair mediated asymmetric synthesis of a configurationally stable mononuclear tris(diimine) iron(II) complex. Angew Chem Int Ed 2002;41:2317-2319.
36. Pasquini C, Desvergnes-Breuil V, Jodry JJ, Dalla Cort A, Lacour J. Chiral anion mediated asymmetric induction onto chiral diquats. Tetrahedron Lett 2002;43:423-426.
37. Pérollier C, Constant S, Jodry JJ, Bernardinelli G, Lacour J. Mannose derived hexacoordinated phosphate-a generally efficient chiral anion for asymmetric applications. Chem Commun 2003:2014-2015.
38. Jodry JJ, Frantz R, Lacour J. Supramolecular stereocontrol of octahedral metal-centered chirality. Ligand modulation. Inorg Chem 2004; 43:3329-3331.
39. Constable EC, Frantz R, Housecraft CE, Lacour J, Mahmood A. Chiral induction in a ribose-decorated metallostar through intrinsic and interionic diastereomeric interactions. Inorg Chem 2004; 43(16):4817-4819.
40. Le Bouder T, Maury O, Le Bozec H, Ledoux I, Zyss J. Synthesis of a highly thermally stable octupolar polyimide for nonlinear optics. Chem Commun 2001(23):2430-2431.
41. Le Bozec H, Le Bouder T, Maury O, Bondon A, Ledoux I, Deveau S, Zyss J. Supramolecular octupolar self-ordering towards nonlinear optics. Adv Mater 2001;13(22):1677-1681.
42. Lacour J, Monchaud D, Marsol C. Effect of the medium on the oxaziridinium-catalyzed enantioselective epoxidation. Tetrahedron Lett 2002;43:8257-8260.
43. Le Bouder T, Maury O, Bondon A, Costuas K, Amouyal E, Ledoux I, Zyss J, Le Bozec H. Synthesis, photophysical and nonlinear optical properties of macromolecular architectures featuring octupolar tris(bipyridine) ruthenium(II) moieties: evidence for a supramolecular self-ordering in a dendritic structure. J Am Chem Soc 2003;125(40): 12284-12299.
44. Viau L, Bidault S, Maury O, Brasselet S, Ledoux I, Zyss J, Ishow E, Nakatani K, Le Bozec H. All-optical orientation of photoisomerizable octupolar zinc(II) complexes in polymer films. J Am Chem Soc 2004; 126(27):8386-8387.
45. Koenig M, Klaebe A, Munoz A, Wolf R. Three identical bidentate ligands complexed with penta- and hexa-coordinate phosphorus: stereospecificity of the phosphorus(V)→phosphorus(VI) transformation. J Chem Soc Perkin Trans 2 1979;(1):40-44.
46. Cavezzan J, Etemad-Moghadam G, Koenig M, Klaebe A. Isomerization of optically active hexacoordinated phosphorus compounds. Evidence for an irregular process. Tetrahedron Lett 1979(9):795-798.
47. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann REJ, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Salvador P, Dannenberg JJ, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA. Gaussian 98, Revision A.11.1. Pittsburgh, PA: Gaussian, Inc.; 2001.
48. Becke AD. Density-functional exchange-energy approximation with correct asymptotic-behavior. Phys Rev A 1988;38(6):3098-3100.
49. Perdew JP. Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Phys Rev B 1986;33(12): 8822-8824.
50. Lee CT, Yang WT, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 1988;37(2):785-789.
51. Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993;98(7):5648-5652.
52. Perdew JP, Chevary JA, Vosko SH, Jackson KA, Pederson MR, Singh DJ, Fiolhais C. Atoms, molecules, solids, and surfaces: applications of the generalized gradient approximation for exchange and correlation. Phys Rev B: Condens Matter Mater Phys 1992;46(11): 6671-6687.
53. Bürgi T, Vargas A, Baiker A. VCD spectroscopy of chiral cinchona modifiers used in heterogeneous enantioselective hydrogenation: conformation and binding of non-chiral acids. J Chem Soc Perkin Trans 2 2002(9):1596-1601.
54. Bürgi T, Urakawa A, Behzadi B, Ernst K-H, Baiker A. The absolute configuration of heptahelicene: a VCD spectroscopy study. New J Chem 2004;28(3):332-334.
55. Mason SF, Peart BJ. Optical-rotatory power of coordination compounds. 17. Circular-dichroism of trisbipyridyl and trisphenanthroline complexes. J Chem Soc Dalton Trans 1973(9):949-955.
56. Mason (Banus) J, Mason SF. The electronic absorption and circular dichroism spectra, and the absolute stereochemiestry of the tris-catechyl- arsenate(V) ion. Tetrahedron 1967;23(4):1919-1927.
57. Hellwinkel D, Mason SF. Circular dichroism and absolute configuration of the tris-biphenyl-ylenephosphorus(V) ion. J Chem Soc B 1970: 640-643.
58. Lacour J, Barchéchath S, Jodry JJ, Ginglinger C. Simple ion-exchange procedure of common anions to TRISPHAT. Application to the purification of cationic species. Tetrahedron Lett 1998;39(7):567-570.
59. Polavarapu PL, He J. Chiral analysis using mid-IR vibrational CD spectroscopy. Anal Chem 2004;76(3):61A-67A.
60. Freedman TB, Cao X, Dukor RK, Nafie LA. Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 2003;15(9):743-758.
61. Stephens PJ, Devlin FJ, Aamouche A. Determination of the structures of chiral molecules using vibrational circular dichroism spectroscopy. ACS Symp Ser 2002;810:18-33.
62. Freedman TB, Cao X, Young DA, Nafie LA. Density functional theory calculations of vibrational circular dichroism in transition metal complexes: identification of solution conformations and mode of chloride ion association for (+)-tris(ethylenediaminato)cobalt(III). J Phys Chem A 2002;106(14):3560- 3565.