Chiral discrimination via nuclear magnetic resonance spectroscopy

Rendiconti Lincei

Volumn 24, Issue 3, 2013, Pages 283-289

  Pelloni, Stefano ^a   Faglioni, Francesco ^a   Lazzeretti, Paolo ^a  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

Chiral discrimination; Magnetic shielding polarisability; NMR spectroscopy

Indexed keywords

CHIRAL CHEMICALS; CHIRAL DISCRIMINATION; DETECTION LIMITS; NUCLEAR MAGNETIC SHIELDINGS; ORDERS OF MAGNITUDE; PERMANENT MAGNETIC DIPOLE; POLARISABILITIES; POLARISABILITY;

MAGNETIC SHIELDING; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLARIZATION;

STEREOCHEMISTRY;

EID: 84883488410     PISSN: 20374631     EISSN: 17200776     Source Type: Journal    
DOI: 10.1007/s12210-013-0242-4     Document Type: Article

References (60)

1. Arimondo E, Glorieux P, Oka T (1977) Observation of inverted infrared lamb dips in separated optical isomers. Opt Commun 23:369-372
2. Barra AL, Robert JB (1996) Parity non-conservation and NMR parameters. Mol Phys 88(4):875-886
3. Barra AL, Robert JB, Wiesenfeld L (1986) Parity non-conservation and NMR observables. Calculation of TL resonance frequency differences in enantiomers. Phys Lett A 115 (9):443-447
4. Barra AL, Robert JB, Wiesenfeld L (1987) Parity non conservation - NMR parameters in chiral molecules. Biosystems 20:57-61
5. Barra AL, Robert JB, Wiesenfeld L (1988) Possible observation of parity nonconservation by high resolution NMR. Europhys Lett 5(3):217-222
6. Bast R, Schwerdtfeger P, Saue T (2006) Parity nonconservation contribution to the nuclear magnetic resonance shielding constants of chiral molecules: a four-component relativistic study. J Chem Phys 125(6):064504
7. Bast R, Koers A, Gomes ASP, Ilias M, Visscher L, Schwerdtfeger P, Saue T (2011) Analysis of parity violation in chiral molecules. Phys Chem Chem Phys 13:864-876
8. Berger R, Laubender G, Quack M, Sieben A, Stohner J, Willeke M (2005) Isotopic chirality and molecular parity violation. Angew. Chem Int Ed Engl 44(23):3623-3626
9. Berger R, Quack M (2000) Electroweak quantum chemistry of alanine: parity violation in gas and condensed phase. Chem Phys Chem 1:57-60
10. Berger R, Quack M, Tschumper GS (2000) Electroweak quantum chemistry for possible precursor molecules in the evolution of biomolecular homochirality. Helv Chim Acta 83:1919-1950
11. Bishop DM (1990) Molecular vibrational and rotational motion in static and dynamic electric fields. Rev Mod Phys 62(2):343-374
12. 2. J Chem Phys 93(1):590-599
13. Buckingham AD (2004) Chirality in NMR spectroscopy. Chem Phys Lett 398:1-5
14. Buckingham AD (2006) Electric polarization induced by nuclear spins. Lect Ser Comput Comput Sci 1-5
15. Buckingham AD, Fischer P (2006) Direct chiral discrimination in NMR spectroscopy. Chem Phys 324:111-116
16. Canet I, Courtieu J, Loewenstein A, Meddour A, Pechine JM (1995) Enantiomeric analysis in a polypeptide lyotropic liquid crystal by deuterium NMR. J Am Chem Soc 117(24):6520-6526. http://pubs.acs.org/doi/pdf/10.1021/ ja00129a015
17. Coriani S, Pecul M, Rizzo A, Jørgensen P, Jaszunski M (2002) Ab initio study of magnetochiral birefringence. J Chem Phys 117(14):6417-6428
18. DALTON2 (2005) An electronic structure program, Release 2.0. http://www.kjemi.uio.no/software/dalton/
19. Darquie B, Stoeffler C, Shelkovnikov A, Daussy C, Amy-Klein A, Chardonnet C, Zrig S, Guy L, Crassous J, Soulard P, Asselin P, Huet TR, Schwerdtfeger P, Bast R, Saue T (2010) Progress toward the first observation of parity violation in chiral molecules by high-resolution laser spectroscopy. Chirality 22(10):SI 870-884
20. -15 et recherche d'un effect de violation de la parité dans les molécules chirales. Ann Phys (Paris), 23(Suppl. C1):225-226
21. Figgen D, Koers A, Schwerdtfeger P (2010) NWHClI: a small and compact chiral molecule with large parity-violation effects in the vibrational spectrum. Angew Chem Int Ed Engl 49(16):2941-2943
22. Frisch MJ, Trucks GW et al (2003) Gaussian 2003, revision b.05. Gaussian Inc., Pittsburgh
23. Kjaer H, Nielsen MR, Pagola GI, Ferraro MB, Lazzeretti P, Sauer SPA (2012) Nuclear magnetic resonance J coupling constant polarizabilities of hydrogen peroxide: a basis set and correlation study. J Comput Chem 33(23):1845-1853
24. Laerdahl JK, Schwerdtfeger P, Quiney HM (2000a) Theoretical analysis of parity-violating energy differences between the enantiomers of chiral molecules. Phys Rev Lett 84(17):3811-3814
25. Laerdahl JK, Wesendrup R, Schwerdtfeger P (2000b) D- or L-alanine: that is the question. Chem Phys Chem 1:60-62
26. Laubender G, Berger R (2003) Ab initio calculation of parity-violating chemicl shifts in NMR spectra of chiral molecules. Chem Phys Chem 4:395-399
27. Laubender G, Berger R (2006) Electroweak quantum chemistry for nuclear-magnetic-resonance-shielding constants: impact of electron correlation. Phys Rev A 74:032105
28. Lazzeretti P (1987) General connections among nuclear electromagnetic shieldings and polarizabilities. Adv Chem Phys 75:507-549
29. Lazzeretti P (2003) Electric and magnetic properties of molecules. Handbook of molecular physics and quantum chemistry, vol. 3, part 1, chap. 3. Wiley, Chichester, pp 53-145
30. Lazzeretti P, Soncini A, Zanasi R (2008) Response tensors for chiral discrimination in NMR spectroscopy. Theor Chem Acc 119:99-106
31. Mason SF, Tranter GE (1983) The parity-violating energy difference between enantiomeric molecules. Chem Phys Lett 94(5):34-37
32. Mason SF, Tranter GE (1984) The parity-violating energy difference between enantiomeric molecules. Mol Phys 53(5):1091-1111
33. Mohr PJ, Taylor BN (2005) CODATA recommended values of the fundamental physical constants: 2002. Rev Mod Phys 77(1):1-107
34. Monaco G, Zanasi R (2011) Searching for a good candidate to perform a chiral nuclear magnetic resonance experiment in disordered phase: a study of 8,9-difluoro-P-hexahelicene. Chirality 23(9)SI: 752-755
35. Nahrwold S, Berger R (2009) Zeroth order regular approximation approach to parity violating nuclear magnetic resonance shielding tensors. J Chem Phys 130(21):214101
36. Olsen J, Jørgensen P (1985) Linear and nonlinear response functions for an exact state and for an mcscf state. J Chem Phys 82(7):3235-3264
37. Orr BJ, Ward JF (1971) Perturbation theory of the non-linear polarization of an isolated system. Mol Phys 20(3):513-526
38. Pagola GI, Ferraro MB, Pelloni S, Lazzeretti P, Sauer SPA (2011a) Electric field effects on nuclear spinspin coupling tensors and chiral discrimination via NMR spectroscopy. Theor Chem Acc 129:359-366
39. Pagola GI, Ferraro MB, Pelloni S, Lazzeretti P, Sauer SPA. (2011b) Electric field effects on nuclear spin-spin coupling tensors and chiral discrimination via NMR spectroscopy (vol 129, pg 359, 2011). Theor Chem Acc 130(1):127
40. Parker D (1991) NMR determination of enantiomeric purity. Chem Rev 91(7):1441-1457. http://pubs.acs.org/doi/pdf/10.1021/cr00007a009
41. a )-1,3-dimethylallene. (2r)-2-methyloxirane, and (2r)-n-methyloxaziridine molecules. J Chem Theor Comput 3(5):1691-1698
42. Quack M (1986) On the measurement of the parity violating energy difference between enantiomers. Chem Phys Lett 132:147-153
43. Quack M, Stohner J (2000) Influence of parity violating weak nuclear potentials on vibrational and rotational frequencies in chiral molecules. Phys Rev Lett 84(17):3807-3810
44. Quack M, Stohner J, Willeke M (2008) High-resolution spectroscopic studies and theory of parity violation in chiral molecules. Ann Rev Phys Chem 59(1):741-769. http://www.annualreviews.org/doi/pdf/10.1146/annurev.physchem.58. 032806.104511 and references therein
45. Rein DW, Hegstrom RA, Sandars PHG (1979) Parity nonconserving energy difference between mirror-image molecules. Phys Lett A 71(5):499-502
46. Robert JB, Barra AL (2001) NMR and parity nonconservation. experimental requirements to observe a difference between enantiomer signals. Chirality 13:699-702
47. Sadlej AJ (1988) Medium-size polarized basis-sets for high-level correlated calculations of molecular electric properties. Collect Czech Chem Commun 53:1995-2016
48. Sears DN, Jameson CJ, Harris RA (2003a) Nuclear magnetic shielding and chirality. I. The shielding tensor of xe interacting with ne helices. J Chem Phys 119:2685-2690
49. Sears DN, Jameson CJ, Harris RA (2003b) Nuclear magnetic shielding and chirality. II. The shielding tensor of a naked spin in Ne helices. J Chem Phys 119(5):2691-2693
50. Sears DN, Jameson CJ, Harris RA (2003c) Nuclear magnetic shielding and chirality. III. The single electron on a helix model. J Chem Phys 119(5):2694-2701
51. Sears DN, Jameson CJ, Harris RA (2004) Nuclear magnetic shielding and chirality. IV. The odd and even character of the shielding response to a chiral potential. J Chem Phys 120(7):3277-3283
52. Sears DN, Jameson CJ, Harris RA (2006) A note on chirality in NMR spectroscopy. J Chem Phys 124(7):096101-1/-2
53. Soncini A, Faglioni F, Lazzeretti P (2003) Parity violating contributions to nuclear magnetic shielding. Phys Rev A 68:033402-1-4
54. Viglione RG, Zanasi R, Lazzeretti P, Ligabue A (2000) Theoretical determination of parity-violating vibrational frequency differences between the enantiomers of the chfclbr molecule. Phys Rev A 62:052516
55. Weijo V (2008) Parity violation in molecular magnetic resonance properties - PhD thesis, Department of Chemistry, University of Helsinki. Dissertation for the degree of Doctor Philosophiae
56. Weijo V, Manninen P, Vaara J (2005) Perturbational calculations of parity-violating effects in nuclear-magnetic-resonance parameters. J Chem Phys 123:054501-1-8
57. Wiesenfeld L (1988) Effect of atomic number on parity-violating energy differences between enantiomers. Mol Phys 64(4):739-745
58. Zanasi R (1996) Coupled Hartree-Fock calculations of molecular magnetic properties annihilating the tranverse paramagnetic current density. J Chem Phys 105(4):1460-1469
59. Zanasi R, Lazzeretti P (1998) On the stabilization of natural l-enantiomers of α amino acids via parity-violating effects. Chem Phys Lett 286(3-4):240-242
60. a )-1,3-dimethylallene. (2r)-2-methyloxirane, and (2r)-n-methyloxaziridine. J Comput Chem 28:2159-2163