메뉴 건너뛰기




Volumn 131, Issue 10, 2009, Pages

Analysis of enantiotopic discrimination in the NMR spectra of prochiral solutes in chiral liquid crystals by symmetry factorization of the Saupe ordering matrix

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-SYMMETRIC; CHIRAL LIQUID CRYSTALS; HOMOTOPIC; MATRIX; NMR SIGNALS; NMR SPECTRUM; PRINCIPAL AXES; SOLUTE MOLECULES; SPECTRAL DEGENERACIES;

EID: 70349292392     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.3197853     Document Type: Article
Times cited : (11)

References (27)
  • 2
    • 0000237404 scopus 로고
    • Chem. Rev. (Washington, D.C.) 0009-2665, () 10.1021/cr00007a009;, Chirality 0899-0042 15, 256 (2003) 10.1002/chir.10190;, (Wiley, New York, 2007).
    • D. Parker, Chem. Rev. (Washington, D.C.) 0009-2665 91, 1441 (1991) 10.1021/cr00007a009; T. J. Wenzel and J. D. Wilcox, Chirality 0899-0042 15, 256 (2003) 10.1002/chir.10190; T. Wenzel, Discrimination of Chiral Compounds Using NMR Spectroscopy (Wiley, New York, 2007).
    • (1991) Discrimination of Chiral Compounds Using NMR Spectroscopy , vol.91 , pp. 1441
    • Parker, D.1    Wenzel, T.J.2    Wilcox, J.D.3    Wenzel, T.4
  • 3
    • 1542484344 scopus 로고
    • 0040-4039,. 10.1016/S0040-4039(01)90560-X
    • J. M. Brown and D. Parker, Tetrahedron Lett. 0040-4039 22, 2815 (1981). 10.1016/S0040-4039(01)90560-X
    • (1981) Tetrahedron Lett. , vol.22 , pp. 2815
    • Brown, J.M.1    Parker, D.2
  • 4
    • 35248900975 scopus 로고    scopus 로고
    • 0957-4166, () 10.1016/j.tetasy.2007.09.016;, Chem. Rec. 1527-8999 5, 396 (2005). 10.1002/tcr.20059
    • E. D. Gomez, T. Brotin, and H. Duddeck, Tetrahedron: Asymmetry 0957-4166 18, 2155 (2007) 10.1016/j.tetasy.2007.09.016; H. Duddeck, Chem. Rec. 1527-8999 5, 396 (2005). 10.1002/tcr.20059
    • (2007) Tetrahedron: Asymmetry , vol.18 , pp. 2155
    • Gomez, E.D.1    Brotin, T.2    Duddeck, H.3    Duddeck, H.4
  • 5
    • 0038683815 scopus 로고
    • 0002-7863, () 10.1021/ja00764a070;, Croat. Chem. Acta 0011-1643 62, 1458 (1979);, Tetrahedron: Asymmetry 0957-4166 8, 3999 (1997) 10.1016/S0957-4166(97) 00586-7;, J. Am. Chem. Soc. 0002-7863 120, 6617 (1998). 10.1021/ja980215x
    • R. R. Fraser, M. A. Petit, and M. Mislow, J. Am. Chem. Soc. 0002-7863 94, 3253 (1972) 10.1021/ja00764a070; R. W. Lang and H. J. Hansen Helv, Croat. Chem. Acta 0011-1643 62, 1458 (1979); A. T. Bilz, T. Stork, and G. Helmchen, Tetrahedron: Asymmetry 0957-4166 8, 3999 (1997) 10.1016/S0957-4166(97)00586-7; J. Huskens, R. Goddard, and M. T. Reetz, J. Am. Chem. Soc. 0002-7863 120, 6617 (1998). 10.1021/ja980215x
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 3253
    • Fraser, R.R.1    Petit, M.A.2    Mislow, M.3    Lang, R.W.4    Hansen Helv, H.J.5    Bilz, A.T.6    Stork, T.7    Helmchen, G.8    Huskens, J.9    Goddard, R.10    Reetz, M.T.11
  • 6
    • 0542427449 scopus 로고
    • 0002-7863, () 10.1021/ja00999a062;, J. Am. Chem. Soc. 0002-7863 111, 8294 (1989) 10.1021/ja00203a049;, Liq. Cryst. 0267-8292 16, 405 (1994). 10.1080/02678299408029165
    • E. Sackmann, S. Meiboom, and L. C. Snyder, J. Am. Chem. Soc. 0002-7863 89, 5981 (1967) 10.1021/ja00999a062; E. Lafontaine, J. P. Bayle, and J. Courtieu, J. Am. Chem. Soc. 0002-7863 111, 8294 (1989) 10.1021/ja00203a049; I. Canet, J. Løvshall, and J. Courtieu, Liq. Cryst. 0267-8292 16, 405 (1994). 10.1080/02678299408029165
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 5981
    • Sackmann, E.1    Meiboom, S.2    Snyder, L.C.3    Lafontaine, E.4    Bayle, J.P.5    Courtieu, J.6    Canet, I.7    Løvshall, J.8    Courtieu, J.9
  • 8
    • 0001070306 scopus 로고
    • 0031-9015, () 10.1143/JPSJ.23.1070;, J. Am. Chem. Soc. 0002-7863 90, 3880 (1968) 10.1021/ja01016a061;, Macromolecules 0024-9297 1, 555 (1968). 10.1021/ma60006a021
    • S. Sobajima, J. Phys. Soc. Jpn. 0031-9015 23, 1070 (1967) 10.1143/JPSJ.23.1070; M. Panar and W. D. Phillips, J. Am. Chem. Soc. 0002-7863 90, 3880 (1968) 10.1021/ja01016a061; E. T. Samulski and A. V. Tobolsky, Macromolecules 0024-9297 1, 555 (1968). 10.1021/ma60006a021
    • (1967) J. Phys. Soc. Jpn. , vol.23 , pp. 1070
    • Sobajima, S.1    Panar, M.2    Phillips, W.D.3    Samulski, E.T.4    Tobolsky, A.V.5
  • 16
    • 46949088455 scopus 로고    scopus 로고
    • Enantiodiscrimination in deuterium NMR spectra of flexible chiral molecules with average axial symmetry dissolved in chiral liquid crystals: The case of tridioxyethylenetriphenylene
    • DOI 10.1021/ja800957a
    • P. Lesot, O. Lafon, H. Zimmermann, and Z. Luz, J. Am. Chem. Soc. 0002-7863 130, 8754 (2008). 10.1021/ja800957a (Pubitemid 351962510)
    • (2008) Journal of the American Chemical Society , vol.130 , Issue.27 , pp. 8754-8761
    • Lesot, P.1    Lafon, O.2    Zimmermann, H.3    Luz, Z.4
  • 18
    • 5544266523 scopus 로고
    • In fact, molecules with cubic symmetry often exhibit splitting due to anisotropic vibrational and rotational modes in the axial potential of the liquid crystal. Such effects are ignored in the present paper;, 0021-9606,. 10.1063/1.446121
    • In fact, molecules with cubic symmetry often exhibit splitting due to anisotropic vibrational and rotational modes in the axial potential of the liquid crystal. Such effects are ignored in the present paper; J. G. Snijders, C. A. de Lange, and E. E. Burnell, J. Chem. Phys. 0021-9606 79, 2964 (1983). 10.1063/1.446121
    • (1983) J. Chem. Phys. , vol.79 , pp. 2964
    • Snijders, J.G.1    De Lange, C.A.2    Burnell, E.E.3
  • 20
    • 85083135164 scopus 로고    scopus 로고
    • NAD NMR, enantiotopic pairs (H/H or D/D) can be observed and become, in fact, enantioisotopomeric pairs, D/H and H/D. Neglecting the (probably very small) isotope effect on the ordering the D-D (or H-H) or D-H pairs are identical. In other words, the molecular recognition mechanisms of H/H (D/D) pairs are the same than D/H pairs. See Refs..
    • NAD NMR, enantiotopic pairs (H/H or D/D) can be observed and become, in fact, enantioisotopomeric pairs, D/H and H/D. Neglecting the (probably very small) isotope effect on the ordering the D-D (or H-H) or D-H pairs are identical. In other words, the molecular recognition mechanisms of H/H (D/D) pairs are the same than D/H pairs. See Refs..
  • 22
    • 0343907269 scopus 로고    scopus 로고
    • The non-reaction of methylene with the carbon-carbon bond
    • DOI 10.1016/S0040-4020(97)00336-0, PII S0040402097003360
    • G. X. Wu, M. Jones, W. Von E. Doering, and L. H. Knox, Tetrahedron 0040-4020 53, 9913 (1997). 10.1016/S0040-4020(97)00336-0 (Pubitemid 27297950)
    • (1997) Tetrahedron , vol.53 , Issue.29 , pp. 9913-9920
    • Wu, G.-X.1    Maitland Jr., J.2    Doering, W.V.E.3    Knox, L.H.4
  • 23
    • 85083144598 scopus 로고    scopus 로고
    • See EPAPS supplementary material at E-JCPSA6-131-033931 for the calculated atomic coordinates of molecular structures experimentally investigated.
    • See EPAPS supplementary material at http://dx.doi.org/10.1063/1.3197853 E-JCPSA6-131-033931 for the calculated atomic coordinates of molecular structures experimentally investigated.
  • 25
    • 0034686048 scopus 로고    scopus 로고
    • Deuterium NMR stereochemical analysis of threo-erythro isomers bearing remote stereogenic centres in racemic and non-racemic liquid crystalline solvents
    • DOI 10.1016/S0957-4166(00)00125-7, PII S0957416600001257
    • C. Canlet, D. Merlet, P. Lesot, A. Meddour, A. Loewenstein, and J. Courtieu, Tetrahedron: Asymmetry 0957-4166 11, 1911 (2000). 10.1016/S0957- 4166(00)00125-7 (Pubitemid 30386941)
    • (2000) Tetrahedron Asymmetry , vol.11 , Issue.9 , pp. 1911-1918
    • Canlet, C.1    Merlet, D.2    Lesot, P.3    Meddour, A.4    Loewenstein, A.5    Courtieu, J.6
  • 26
    • 0035171910 scopus 로고    scopus 로고
    • Characterisation of the structure, deuterium quadrupolar tensors, and orientational order of acenaphthene, a rigid, prochiral molecule, from the NMR spectra of samples dissolved in nematic and chiral nematic liquid crystalline solvents
    • DOI 10.1039/b106069b
    • D. Merlet, J. W. Emsley, J. Jokisaari, and J. Kaski, Phys. Chem. Chem. Phys. 1463-9076 3, 4918 (2001). 10.1039/b106069b (Pubitemid 33078533)
    • (2001) Physical Chemistry Chemical Physics , vol.3 , Issue.22 , pp. 4918-4925
    • Merlet, D.1    Emsley, J.W.2    Jokisaari, J.3    Kaski, J.4
  • 27
    • 0006654015 scopus 로고
    • 0021-9606,. 10.1063/1.1680153
    • Z. Luz and S. Meiboom, J. Chem. Phys. 0021-9606 59, 1077 (1973). 10.1063/1.1680153
    • (1973) J. Chem. Phys. , vol.59 , pp. 1077
    • Luz, Z.1    Meiboom, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.