Vibrational and electronic circular dichroism monitoring of copper(II) coordination with a chiral ligand

Chirality

Volumn 24, Issue 6, 2012, Pages 451-458

  Wu, Tao ^a   Zhang, Xiao Peng ^a   Li, Cheng Hui ^a   Bouř, Petr ^b   Li, Yi Zhi ^a   You, Xiao Zeng ^a  

^a NANJING UNIVERSITY   (China)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

chiral coordination compounds; circular dichroism; coordination process; density functional theory calculations; vibrational circular dichroism

Indexed keywords

CAMPHOR; CUPRIC ION; LIGAND; MACROCYCLIC COMPOUND;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CIRCULAR DICHROISM; CONTROLLED STUDY; CRYSTAL STRUCTURE; ENANTIOMER; PRIORITY JOURNAL; QUANTUM CHEMISTRY; SPECTROSCOPY; X RAY DIFFRACTION;

EID: 84861580385     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22010     Document Type: Article

References (48)

1. Berova N, Nakanishi K, Woody RW, editors. Circular dichroism, principles and applications, 2nd ed. New York: Wiley; 2000.
2. Urbanová M, Maloň P,. Circular dichroism spectroscopy. In:, Schalley C, editor. Analytical methods in supramolecular chemistry. Weinheim: Wiley-VCH; 2007, p 265-303.
3. Berova N, Bari LD, Pescitelli G,. Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. Chem Soc Rev 2007; 36: 914-931.
4. Stephens PJ, Devlin FJ, Pan JJ,. The determination of the absolute configurations of chiral molecules using vibrational circular dichroism (VCD) spectroscopy. Chirality 2008; 20: 643-663.
5. Sadlej J, Dobrowolski JC, Rode JE,. VCD spectroscopy as a novel probe for chirality transfer in molecular interactions. Chem Soc Rev 2010; 39: 1478-1488.
6. Urbanová M, Setnička V, Devlin FJ, Stephens PJ,. Determination of molecular structure in solution using vibrational circular dichroism spectroscopy: the supramolecular tetramer of S-2,2'-dimethyl-biphenyl- 6,6'-dicarboxylic acid. J Am Chem Soc 2005; 127: 6700-6711.
7. Pessoa JC, Correia I, Goncalves G, Tomza I,. Circular dichroism in coordination compounds. J Argent Chem Soc 2009; 97: 151-165.
8. Yang GC, Xu YJ, Hou JB, Zhang H, Zhao YF,. Determination of the absolute configurations of the pentacoordinate chiral phosphorus compounds in solution using vibrational circular dichroism spectroscopy and density functional theory. Chem Eur J 2010; 16: 2518-2527.
9. Julínek O, Urbanová M, Lindner W,. Enantioselective complexation of carbamoylated quinine and quinidine with N-blocked amino acids: vibrational and electronic circular dichroism study. Anal Bioanal Chem 2009; 393: 303-312.
10. Montigny FD, Guy L, Pilet G, Vanthuyne N, Roussel C, Lombardi R, Freedman TB, Nafie LA, Crassous J,. Subtle chirality in oxo- and sulfidorhenium(V) complexes. Chem Commun 2009; 32: 4841-4843.
11. Abbate S, Lebon F, Gangemi R, Longhi G, Spizzichino S, Ruzziconi R,. Electronic and vibrational circular dichroism spectra of chiral 4-X-[2.2]paracyclophanes with X containing fluorine atoms. J Phys Chem A 2009; 113: 14851-14859.
12. Gottarelli G, Lena S, Masiero S, Pieraccini S, Spada GP,. The use of circular dichroism spectroscopy for studying the chiral molecular self-assembly: an overview. Chirality 2008; 20: 471-485.
13. Amouri H, Gruselle M,. Chirality in transition metal chemistry: molecules, supramolecular assemblies and materials. Chichester: Wiley-VCH; 2008.
14. Crassous J,. Chiral transfer in coordination complexes: towards molecular materials. Chem Soc Rev 2009; 38: 830-845.
15. Knof U, Zelewsky A,. Predetermined chirality at metal centers. Angew Chem Int Ed 1999; 38: 302-322.
16. He YN, Cao XL, Nafie LA, Freedman TB,. Ab initio VCD calculation of a transition-metal containing molecule and a new intensity enhancement mechanism for VCD. J Am Chem Soc 2001; 123: 11320-11321.
17. Nafie LA,. Theory of vibrational circular dichroism and infrared absorption: extension to molecules with low-lying excited electronic states. J Phys Chem A 2004; 108: 7222-7231.
18. Sato H, Shirotani D, Yamanari K, Kaizaki S,. Vibrational circular dichroism of Δ-SAPR-8-tetrakis [(+)-heptafluorobutyrylcamphorato] lanthanide(III) complexes with an encapsulated alkali metal ion. Inorg Chem 2010; 49: 356-358.
19. Sato H, Taniguchi T, Nakahashi A, Monde K, Yamagishi A,. Effects of central metal ions on vibrational circular dichroism spectra of tris-(β-diketonato)metal(III) complexes. Inorg Chem 2007; 46: 6755-6766.
20. Wu T, Li CH, Li YZ, Zhang ZG, You XZ,. Synthesis, structure and chiroptical study of chiral macrocyclic imine nickel (II) coordination compounds derived from camphor. Dalton Trans 2010; 39: 3227-3232.
21. Cheeseman JR, Frisch MJ, Devlin FJ, Stephens PJ,. Ab initio calculation of atomic axial tensors and vibrational rotational strengths using density functional theory. Chem Phys Lett 1996; 252: 211-220.
22. Stephens PJ,. Theory of vibrational circular dichroism. J Phys Chem 1985; 89: 748-752.
23. SAINT-Plus, version 6.02. Madison, WI: Bruker Analytical X-ray System; 1999.
24. Sheldrick GM,. SADABS. An empirical absorption correction program. Madison, WI: Bruker Analytical X-ray Systems; 1996.
25. Sheldrick GM,. SHELXTL-97. Göttingen, Germany: Universität of Göttingen; 1997.
26. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Jr., Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ,. Gaussian 09, Revision A.02. Wallingford CT: Gaussian, Inc.; 2009.
27. Telfer SG, McLean TM, Waterland MR,. Exciton coupling in coordination compounds. Dalton Trans 2011; 40: 3097-3108.
28. Harada N, Nakanishi K,. The exciton chirality method and its application to configurational and conformational studies of natural products. Acc Chem Res 1972; 5: 257-263.
29. Ziegler M, Zelewsky A,. Charge-transfer excited state properties of chiral transition metal coordination compounds studied by chiroptical spectroscopy. Coord Chem Rev 1998; 177: 257-300.
30. Wojtczak A, Szlyk E, Jaskolski M, Larsen E,. An optically active nickel (II) Schiff base coordination compound N, N'-(1R,2R)-(-)-1,2- cyclehexylenebis(salicylideneiminato)nickel(II). Acta Chem Scand 1997; 51: 274-278.
31. Pasini A, Gullotti M, Ugo R,. Optically active complexes of Schiff bases. Part 4. An analysis of the circular-dichroism spectra of some complexes of different co-ordination numbers with quadridentate Schiff bases of optically active diamines. JCS Dalton Trans 1977; 4:3 346-356.
32. Fan J, Autschbach J, Ziegler T,. Electronic structure and circular dichroism of tris(bipyridyl) metal complexes within density functional theory. Inorg Chem 2010; 49: 1355-1362.
33. Wang F, Zhang H, Li L, Hao HQ, Wang XY, Chen JG,. Synthesis and characterization of chiral nickel (II) Schiff base complexes and their CD spectra-absolute configuration correlations. Tetrahedron Asymmetry 2006; 17: 2059-2063.
34. Bosnich B,. The application of exciton theory to the determination of the absolute configurations of inorganic complexes. Acc Chem Res 1969; 2: 266-273.
35. Nicu VP, Autschbach J, Baerends EJ,. Enhancement of IR and VCD intensities due to charge transfer. Phys Chem Chem Phys 2009; 11: 1526-1538.
36. Freedman TB, Cao XL, 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: 3560-3565.
37. Nakamoto K,. Infrared spectra of inorganic and coordination compounds. New York: Wiley; 1978.
38. Gangemi F, Gangemi R, Longhi G, Abbate S,. Calculations of overtone NIR and NIR-VCD spectra in the local mode approximation: camphor and camphorquinone. Vib Spectrosc 2009; 50: 257-267.
39. Abbate S, Burgi LF, Gangemi F, Gangemi R, Lebon F, Longhi G, Pultz VM, Lightner DA,. Comparative analysis of IR and vibrational circular dichroism spectra for a series of camphor-related molecules, J Phys Chem A 2009; 113: 11390-11405.
40. Longhi G, Abbate S, Gangemi R, Giorgio E, Rosini C,. Fenchone, camphor, 2-methylenefenchone and 2-methylenecamphor: a vibrational circular dichroism study. J Phys Chem A 2006; 110: 4958-4968.
41. Longhi G, Gangemi R, Lebon F, Castiglioni E, Abbate S, Pultz VM, Lightner DA,. A comparative study of overtone CH-stretching vibrational circular dichroism spectra of fenchone and camphor. J Phys Chem A 2004; 108: 5338-5352.
42. Laux L, Pultz V, Abbate S, Havel HA, Overend J, Moscowitz A,. Inherently dissymmetric chromophores and vibrational circular dichroism. The CH2 CH2 C*H fragment. J Am Chem Soc 1982; 104: 4276-4278.
43. Gangemi R, Longhi G, Lebon F, Abbate S, Laux L,. Vibrational excitons in CH-stretching fundamental and overtone vibrational circular dichroism spectra. Monatshefte für Chemie 2005; 136: 325-345.
44. 3 - n] (n = 0 ~ 3, tfac = 3- trifluoroacetylcamphorato and acac = acetylacetonato). Inorg Chem 2009; 48: 4354-4361.
45. Sato H, Unoa H, Nakano H,. Identification of geometrical isomers using vibrational circular dichroism spectroscopy: a series of mixed-ligand complexes of diamagnetic Co(III) ions. Dalton Trans 2011; 40: 1332-1337.
46. Johannessen C, Thulstrup PW,. Vibrational circular dichroism spectroscopy of a spin-triplet bis-(biuretato) cobaltate(III) coordination compound with low-lying electronic transitions. Dalton Trans 2007; 36: 1028-1033.
47. Bormett RW, Smith GD, Asher SA, Barrick D, Kurtz DM,. Vibrational circular dichroism measurements of ligand vibrations in haem and non-haem metalloenzymes. Faraday Discuss 1994; 99: 327-339.
48. Bouř P, McCann J, Wieser H,. Measurement and calculation of absolute rotational strengths for camphor, α-pinene, and borneol. J Phys Chem A 1998; 102: 102-110.