Conformational sensitivity of chiroptical spectroscopic methods: 6,6'-dibromo-1,1'-bi-2-naphthol

Journal of Physical Chemistry A

Volumn 113, Issue 18, 2009, Pages 5423-5431

  Polavarapu, Prasad L ^a   Jeirath, Neha ^a   Walia, Sheena ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-NAPHTHOL; ABSOLUTE CONFIGURATION; B3LYP DENSITY FUNCTIONAL; BASIS SETS; ELECTRONIC CIRCULAR DICHROISM; EXPERIMENTAL DATA; EXPERIMENTAL SPECTRA; HYDROXYL GROUPS; OPTICAL ROTATORY DISPERSION; PCM MODEL; QUANTUM CHEMICAL; SOLVENT INFLUENCE; SPECTRAL PATTERNS; SPECTRAL SENSITIVITY; SPECTROSCOPIC METHOD; VIBRATIONAL ABSORPTION; VIBRATIONAL CIRCULAR DICHROISM;

ABSORPTION; DICHROISM; ELECTROCHEMICAL SENSORS; ELECTROCHROMIC DEVICES; MOLECULAR SPECTROSCOPY; OPTICAL ROTATION; PHENOLS; REDUCTION; SPECTRUM ANALYSIS;

CONFORMATIONS;

EID: 65649105777     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp811055y     Document Type: Article

References (49)

1. Aydin, J.; Kumar, K. S.; Sayah, M. J.; Wallner, O. A.; Szabo, K. J. Synthesis and catalytic application of chiral 1,1'-bi-2-naphthol- and bi- phenanthrol-based pincer complexes: Selective allylation of sulfonimines with allyl stannane and allyl trifluoroborate. J. Org. Chem. 2007, 72 (13), 4689-4697.
2. Hu, Q.; Vitharana, D.; Zheng, X.; Wu, C.; Kwan, C. M. S.; Pu, L. Poly(1,1'-bi-2-naphthol)s: Synthesis, Characterization, and Application in Lewis Acid Catalysis. J. Org. Chem. 1996, 61, 8370-8377.
3. Chow, H.; Wan, C.; Ng, M. A versatile method for the resolution and absolute configurational assignment of substituted 1,1'-bi-2-naphthols. J. Org. Chem. 1996, 61, 8712-8714.
4. (4)Superchi, S.; Giorgio, E.; Rosini, C. Structural determination by circular dichroism spectra analysis using coupled oscillator methods: An update of the application of the DeVoe Polarizability model. Chirality 2004, 16, 422-451.
5. Kabuto, K.; Yasuhara, F.; Yamaguchi, S. Determination of absolute configuration of axially chiral biaryls. Tetrahed Lett 1981, 22, 659-662.
6. Mason, S. F.; Seal, R. H.; Roberts, D. R. Optical activity in the biaryl series. Tetrahedron 1974, 30, 1671-1682.
7. (a) Proni, G.; Spada, G. P.; Lustenberger, P.; Welti, R.; Diedrich, F. Conformational analysis in solution of C2-symmetric 1,1'-binaphthyl derivatives by circular dichroism spectroscopy and Cholesteric induction in nematic mesophases. J. Org. Chem. 2000, 65, 5522-5527.
8. (b) Rosini, C.; Rosati, I.; Spada, G. P. A Conformational analysis of mono and dialkyl ethers of 2,2'-dihydroxy-1,1'-binaphthalene by circular dichroism spectros- copy and cholesteric induction in nematic liquid crystals. Chirality 1995, 7, 353-358.
9. Bari, L. D.; Pescitelli, G.; Salvadori, P. Conformational study of 2,2'-homosubstituted 1,1'-binaphthyls by means of UV and CD spectros-copy. J. Am. Chem. Soc. 1999, 121, 7998-8004.
10. Sahnoun, R.; Koseki, S.; Fujimura, Y. Theoretical investigation of 1,1'-bi-2-naphthol isomerization. J. Mol. Struct. 2005, 735- 736, 315-324.
11. Sogah, G. D. Y.; Cram, D. J. Host-Guest Complexation. 14. Host Covalently Bound to Polystyrene Resin for Chromatographic Resolution of Enantiomers of Amino Acid and Ester. J. Am. Chem. Soc. 1979, 101, 3035-3042.
12. Qian, C.; Huang, T.; Zhu, C.; Sun, J. Synthesis of 3,3'-, 6,6'- and 3,3',6,6'-substituted binaphthols and their application in the asymmetric hydrophosphonylation of aldehydes-an obvious effect of substituents of BINOL on the enantioselectivity. J. Chem. Soc. Perkin I 1998, 2097-2103.
13. Deubent, H.-J.; Shibaevs, P. V.; Vinokurs, R.; Bjornholmt, T.; Schaumburg, K.; Bechgaards, K.; Shibaevs, V. P. New 6,6'-disubstituted- binaphthol derivatives as chiral dopants: Synthesis and temperature dependence of molecular conformations. Liq. Cryst. 1996, 21, 327-340.
14. Pirkle, W. H.; Schreiner, J. L. Chiral High-pressure Liquid Chromatographic Stationary Phases. 4. Separation of the Enantiomers of Bi-beta-naphthols and Analogues. J. Org. Chem. 1981, 46, 4988-4991.
15. (a) Barron, L. D. Molecular light scattering and optical activity, 2nd ed.; Cambridge University Press, 2004.
16. (b) Polavarapu, P. L. Vibrational Spectra: Principles and applications with emphasis on optical activity; Elsevier: Amsterdam, 1998.
17. Polavarapu, P. L. Why is it Important to Simultaneously Use More Than One Chiroptical Spectroscopic Method for Determining the Structures of Chiral Molecules. Chiraity 2008, 20, 664-672.
18. Nakao, K.; Kyogoku, Y.; Sugeta, H. Vibrational circular dichroism of the OH-stretching vibration in 2,2'-dihydroxy-1,1'-binaphthyl. Faraday Discuss. 1994, 99, 77-85.
19. Setnicka, V.; Urbanova, M.; Bour, P.; Kral, V.; Volka, K. Vibrational circular dichroism of 1,1'-binaphthyl derivatives: Experimental and theoretical study. J. Phys. Chem. A 2001, 105, 8931-8938.
20. Cao, H.; Ben, T.; Su, Z. M.; Zhang, M.; Kan, Y. H.; Yan, X.; Zhang, W. J.; Wei, Y. Absolute configuration determination of a new chiral rigid bisetherketone macrocycle containing binaphthyl and thioether moieties by vibrational circular dichroism. Macromol. Chem. Phys. 2005, 206, 11401145.
21. Freedman, T. B.; Cao, X. L.; Rajca, A.; Wang, H.; Nafie, L. A. Determination of absolute configuration in molecules with chiral axes by vibrational circular dichroism: A C-2-symmetric annelated heptathiophene and a D-2-symmetric dimer of 1,1'-binaphthyl. J. Phys. Chem. A 2003, 107, 7692-7696.
22. Petrovic, A. G.; Vick, S. E.; Polavarapu, P. L. Determination of the absolute Stereochemistry of Chiral Biphenanthryls in Solution Phase Using Chiroptical Spectroscopic Methods: 2,2'-diphenyl-[3,3'-biphenan- threne]-4,4'-diol". Chirality 2008, 20, 501-510.
23. (a) Galwas, P. A. Ph.D. Thesis, University of Cambridge, Cambridge, 1983.
24. (b) Buckingham, A. D.; Fowler, P. W.; Galwas, P. A. Velocity-dependent property surfaces and the theory of vibrational circular dichroism. Chem. Phys. 1987, 112, 1-14.
25. Stephens, P. J. Theory of vibrational circular dichroism. J. Phys. Chem. 1985, 89, 748-752.
26. (a) Gaussian 03, www.gaussian.com.
27. Turbomole, www.turbomole.com.
28. (c) Amsterdam Density Functional Program, www.scm.com.
29. (d) Dalton program, www.kjemi.uio.no/software/dalton/.
30. (b) PSI 3.2, www.psicode.org.
31. Polavarapu, P. L. Ab initio molecular optical rotations and absolute configurations. Mol. Phys. 1997, 91, 551-554.
32. For recent reviews see:(a) Crawford, T. D.; Tam, M. C.; Abrams, M. L. The current state of ab initio calculations of optical rotation and electronic circular dichroism spectra. J. Phys. Chem. A 2007, 111 (48), 12057-12068
33. (b) Crawford, T. D. Ab initio calculation of molecular chiroptical properties. Theor. Chem. Acc. 2006, 115 (4), 227-245.
34. (c) Polavarapu, P.L. Optical rotation: Recent advances in determining the absolute configuration. Chirality 2002, 14, 768-781.
35. (c) Polavarapu, P.L. Optical rotation: Recent advances in determining the absolute configuration. Chirality 2003, 15, 284-285.
36. (a) Wilson, S. M.; Wiberg, K. B.; Cheeseman, J. R.; Frisch, M. J.; Vaccaro, P. H. Nonresonant optical activity of isolated organic molecules
37. (b) Miller, T.; Wiberg, K.; Vaccaro, P. H. An optical mounting system for cavity ring-down polarim- etry. Rev. Sci. Instrum. 2002, 73, 1340-1342.
38. (c) Miller, T.; Wiberg, K. B.; Vaccaro, P. H.; Cheeseman, J. R.; Frisch, M. J. Cavity ring-down polarimetry (CRDP): theoretical and experimental characterization. J. Opt. Soc. Am. B 2002, 19, 125-141.
39. (d) Miller, T.; Wiberg, K. B.; Vaccaro, P. H. Cavity Ring-down polarimetry: A new scheme for probing circular birefringence and circular dichroism in the gas phase. J. Phys. Chem. A 2000, 104, 5959-5968.
40. (a) Rudolph, M.; Autschbach, J. Fast generation of nonresonant and resonant optical rotatory dispersion curves with the help of circular dichroism calculations and Kramers-Kronig transformations. Chirality 2008, 20, 995-1008.
41. (b) Jiemchooroj, A.; Norman, P. Electronic circular dichroism spectra from the complex polarization propagator. J. Chem. Phys. 2007, 126, 134102.
42. (c) Pedersen, T. B.; Koch, H.; Ruud, K. Coupled cluster response calculation of natural chiroptical spectra. J. Chem. Phys. 1999, 110, 2883-2892.
43. (d) Diedrich, C.; Grimme, S. Systematic Investigation of Modern Quantum Chemical Methods to Predict Electronic Circular Dichroism Spectra. J. Phys. Chem. A 2003, 107, 2524-2539.
44. (e) Stephens, P. J.; McCann, D. M.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J. Determination of the absolute configuration of [3(2)](1,4) barrelenophanedicarbonitrile using concerted time-dependent density functional theory calculations of optical rotation and electronic circular dichroism. J. Am. Chem. Soc. 2004, 126, 7514-7521.
45. Harada, N.; Nakanishi, K. Circular Dichroism Spectroscopy: Exciton coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
46. Wiberg, K. B.; Wang, Y.; Wilson, S. M.; Vaccaro, P. H.; Cheeseman, J. R. J. Phys. Chem. A 2005, 109, 3448-3453.
47. Mennucci, B.; Tomasi, J.; Cammi, R.; Chheseman, J. R.; Frisch, M. J.; Devlin, F. J.; Gabriel, S.; Stephens, P. J. J. Phys. Chem. A 2002, 106, 6102-6113.
48. Polavarapu, P, L. Kramers-Kronig transformation for optical rotatory dispersion studies. J. Phys. Chem. A 2005, 109, 7013-7023.
49. Bauernschmitt, R.; Ahlrichs, R. Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory. Chem. Phys. Lett. 1996, 256, 454-464.