Vibrational circular dichroism in hydrogen bond systems: Part II. Vibrational circular dichroism of the OH stretching vibration in 2,2-dimethyl-1,3-dioxolane-4-methanol

作者: Yoshihiko Nakao , Yoshimasa Kyogoku , Hiromu Sugeta

DOI: 10.1016/0022-2860(86)80284-8

关键词: Intramolecular forceDioxolaneCrystallographyVibrationMethanolVibrational circular dichroismStereochemistryChemistryHydrogen bondPrimary alcoholCircular dichroism

摘要: Abstract Vibrational circular dichroism (VCD) of the OH stretching band in 2,2-dimethyl-1,3- dioxolane-4-methanol has been studied. The vibration for intramolecularly hydrogen-bonded species (R)-enantiomer gives rise to a positive VCD but no hydrogen-bond free species. It is shown that G − + conformation intramolecular hydrogen bond system vibration. thermodynamic parameters equilibrium between and have determined as Δ H =−7.8 kJ mol −1 S = −18 K .

参考文章(34)
P.J. Krueger, H.D. Mettee, Spectroscopic studies of alcohols: Part VII. Intramolecular hydrogen bonds in ethylene glycol and 2-methoxyethanol Journal of Molecular Spectroscopy. ,vol. 18, pp. 131- 140 ,(1965) , 10.1016/0022-2852(65)90069-X
E. G. Höhn, O. E. Weigang, Electron Correlation Models for Optical Activity Journal of Chemical Physics. ,vol. 48, pp. 1127- 1137 ,(1968) , 10.1063/1.1668773
R.J.W. Le Fèvre, Molecular Refractivity and Polarizability Advances in Physical Organic Chemistry. ,vol. 3, pp. 1- 90 ,(1965) , 10.1016/S0065-3160(08)60298-1
C.J. Barnett, A.F. Drake, R. Kuroda, S.F. Mason, A dynamic polarization model for vibrational optical activity and the infrared circular dichroism of a dihydro[5]helicene Molecular Physics. ,vol. 41, pp. 455- 468 ,(1980) , 10.1080/00268978000102891
Edwin N. Lassettre, Michael A. Dillon, Singlet‐triplet energy differences calculated from generalized oscillator strengths Journal of Chemical Physics. ,vol. 59, pp. 4778- 4783 ,(1973) , 10.1063/1.1680692
Martin Moskovits, Arthur Gohin, Vibrational circular dichroism: effect of charge fluxes and bond currents The Journal of Physical Chemistry. ,vol. 86, pp. 3947- 3950 ,(1982) , 10.1021/J100217A013
Christopher J. Barnett, Alexander F. Drake, Stephen F. Mason, The optical activity of the H-stretching vibrational modes of calycanthine and IRCD determinations of absolute configuration Tetrahedron Letters. ,vol. 21, pp. 391- 394 ,(1980) , 10.1016/S0040-4039(01)85482-4
Gunnar Aksnes, Per Albriktsen, Paul Juvvik, Hugo Thelin, Berndt Sjöberg, Erik Larsen, Studies of Cyclic Acetal and Ketal Isomers of Glycerol. Acta Chemica Scandinavica. ,vol. 19, pp. 920- 930 ,(1965) , 10.3891/ACTA.CHEM.SCAND.19-0920
Teresa B. Freedman, Gregory A. Balukjian, Laurence A. Nafie, Enhanced vibrational circular dichroism via vibrationally generated electronic ring currents Journal of the American Chemical Society. ,vol. 107, pp. 6213- 6222 ,(1985) , 10.1021/JA00308A012
Gunnar Aksnes, Per Albriktsen, Tauno Kujanpää, Bengt von Hofsten, D. H. Williams, E. Bunnenberg, Carl Djerassi, Ruth Records, Studies of Intramolecular Hydrogen Bonding in Cyclic Acetal Isomers of Glycerol. Acta Chemica Scandinavica. ,vol. 20, pp. 1330- 1334 ,(1966) , 10.3891/ACTA.CHEM.SCAND.20-1330