Transfer of Chirality by Dithiophosphate Ligands and Chiral Discrimination in the Stereoselective Formation of Square-Planar Ni(II) Complexes

Chirality

Volumn 16, Issue 4, 2004, Pages 251-262

  Biscarini, Paolo ^a   Benedetti, Michele ^a,d   Ferranti, Francesco ^a   Kuroda, Reiko ^b,c   Foresti, Elisabetta ^a   Sabatino, Piera ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF TOKYO   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^d UNIVERSITY OF SALENTO   (Italy)

Author keywords

Coordination compounds; Crystal packing; Crystal structures; Induced CD; Stereoselective synthesis

Indexed keywords

CYCLO O,O' (1,2 DIMETHYLETHYLNE)DITHIOPHOSPHATE DERIVATIVE; DITHIOPHOSPHATE; ETHYLENE DERIVATIVE; LIGAND; METHYL GROUP; NICKEL COMPLEX; PHOSPHOROTHIOIC ACID DERIVATIVE; PHOSPHORUS DERIVATIVE; TARTARIC ACID DERIVATIVE; TARTARIC ACID DIETHYL ESTER; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; CHIRALITY; CHROMATOPHORE; COMPLEX FORMATION; CONFERENCE PAPER; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; CRYSTALLIZATION; DISSOCIATION CONSTANT; ENANTIOMER; HYDROGEN BOND; MOLECULAR INTERACTION; PRIORITY JOURNAL; RACEMIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 1842853086     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20022     Document Type: Conference Paper

References (28)

1. Livingstone SE. Comprehensive coordination chemistry. Wilkinson G, Gillard RD, McCleverty JA, editors. Oxford: Pergamon; 1987; vol. 2, p 643-644, and references therein.
2. Haiduc J, Sowerby DB, Shao-Fang Lu. Stereochemical aspects of phosphor-1,1-dithiolato metal complexes (dithiophosphates, dithiophosphinates): coordination patterns, molecular structures and supramolecular associations. Polyhedron 1995;14:3389-3472.
3. Haiduc J, Sowerby DB. Stereochemical aspects of phosphor-1,1-dithiolato metal complexes: coordination patterns, molecular structures and supramolecular associations in dithiophosphinates and related compounds. Polyhedron 1996;15:2469-2521.
4. Cavell RG, Creed B, Gelmini L, Law DJ, McDonald R, Sanger AR, Somogyvari A. Design, syntheses and application of new phosphine and dithiophosphinate complexes of nickel: catalyst precursors for the oligomerization of ethylene. Inorg Chem 1998;37:757-763.
5. Knopf U, von Zelewsky A. Predetermined chirality at metal centers. Angew Chem Int Ed 1999;38:302-322.
6. von Zelewsky A. Stereochemistry of coordination compounds. Chichester, UK: John Wiley & Sons; 1996, and references therein.
7. 4, (Ln=Nd,Eu). Inorg Chim Acta 1983;74:65-75.
8. 3. Inorg Chim Acta 1985;99:183-185.
9. 3 symmetry. Synthesis and characterization. Inorg Chem 1995;34:4618-4626.
10. 2. Enantiomer 1999;4:57-61.
11. 3}. Inorg Chim Acta 1985;99:189-194.
12. 3}. J Chem Soc Dalton Trans 1990:3393-3397.
13. Kuroda R. Chiral discriminations and crystal packing. Two diastereomeric compounds involving complex ions of D3 symmetry, [tris (ethylenediamine)cobalt(III)] and [tris(oxalato)rhodate(III)]. Inorg Chem 1991;30:4954-4959.
14. Sheldrick GM. Phase annealing in SHELX-90: direct methods for larger structures. Acta Crystallogr A 1990;46:467-473.
15. Sheldrick GM. SHELXL-93, Program for crystal structure refinement. University of Göttingen, Germany; 1993.
16. Flack HD. On enantiomorph-polarity estimation. Acta Crystallogr A 1983;39:876-881.
17. Jacques J, Collet A, Wilen SH. Enantiomers, racemates and resolutions. New York: Wiley-Interscience; 1981.
18. Bond lengths and angles are reported in supporting data.
19. Woitczak A, Szlyk E, Jaskólski M, Larsen E. An optically active nickel(II) Schiff base coordination compound N,N′ -(1R,2R)-(-)-1,2-cyclohexylenebis(salicylideneiminato)nickel(II). Acta Chem Scand 1997;51:274-278.
20. Eliel EL, Wilen SH, Mander LN. Stereochemistry of organic compounds. New York: Wiley-Interscience; 1994.
21. Hawkins CJ. Absolute configuration of metal complexes. New York: Wiley-Interscience; 1971.
22. Merlet D, Emsley JW, Lerot P, Courtieu J. The relationship between molecular symmetry and second-rank orientational order parameters for molecules in chiral liquid crystalline solvents. J Chem Phys 1999;111:15:6890-6896.
23. Jørgensen CK. Absorption spectra of transition group complexes of sulphur-containing ligands. J Inorg Nucl Chem 1962;24:1571-1585.
24. Benesy HA, Hildebrand JH. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 1949;71:2703-2707.
25. Mason SF. Molecular optical activity and the chiral discrimination. Cambridge, UK: Cambridge University Press; 1982. p 208-211.
26. Craig DP. Chiral discrimination In: Mason SF, editor. Optical activity and chiral discrimination. Dordrecht: Reidel; 1979. p 293-318.
27. Pfeiffer P, Quehl K. Über einen neuen effect in lösungen optischaktiver substanzen. Chem Ber 1931;64:2667.
28. Drake A, Levey JR, Mason SF, Prosperi T. Energy discriminations between the enantiomers of tris-chelate co-ordination compounds in the fluid phase. Inorg Chim Acta 1982;57:151-159.