Vibrational circular dichroism of the OH-stretching vibration in 2,2′-dihydroxy-1,1′-binaphthyl

Vibrational circular dichroism (VCD) spectra in the near-IR region of (R)-2,2′-dihydroxy-1,1′-binaphthyl have been obtained in various organic solvents. It is found that the VCD feature of the OH-stretching vibration exhibits a remarkable change with solvent polarity reflecting different states of the hydrogen bond. A strong negative VCD band accompanying a weak positive band on the low-wavenumber side is observed for the OH-stretching vibration in dilute CCl4 solution. The strongly negative-biased bisignate feature is interpreted as the sum of the conservative bisignate couplet and the negative monosignate term. The strong negative VCD is attributed to the dynamic polarization mechanism due to the large anisotropy of polarizability of the naphthalene ring in the intramolecular hydrogen-bond structure. The bisignate feature is found to originate in the three-centre dynamic polarization coupling mechanism as well as the classical electric dipole–dipole coupling mechanism in the degenerate coupled-oscillator system.

[1]  L. Nafie,et al.  Theoretical formalism and models for vibrational circular dichroism intensity , 1994 .

[2]  M. Malagoli,et al.  Calculation of Infrared and Vibrational Circular-dichroism Intensities Via Nuclear Electromagnetic Shieldings , 1993 .

[3]  A. Shanzer,et al.  Vibrational CD studies of interchain hydrogen‐bonded tripodal peptides , 1992, Biopolymers.

[4]  R. Bursi,et al.  Ring current contributions to vibrational circular dichroism ? Ab initio calculations for methyl glycolate-d1 and -d4 , 1991 .

[5]  Y. Kyōgoku,et al.  Vibrational circular dichroism in hydrogen bond systems: Part III. Vibrational circular dichroism of the OH stretching vibrations of 1,2-diols and β-methoxyalcohols , 1991 .

[6]  A. Rauk.  Vibrational Circular Dichroism Intensities: Ab Initio Calculations , 1991 .

[7]  R. Bursi,et al.  Vibrationally induced ring currents? The vibrational circular dichroism of methyl lactate , 1990 .

[8]  N. Handy,et al.  The vibrational circular dichroism of dimethylcyclopropane in the C–H stretching region , 1988 .

[9]  D. Young,et al.  Vibrational circular dichroism in transition-metal complexes. 4. Solution conformation of .LAMBDA.-mer- and .LAMBDA.-fac-tris(.beta.-alaninato)cobalt(III) , 1987 .

[10]  P. Fowler,et al.  Velocity-dependent property surfaces and the theory of vibrational circular dichroism , 1987 .

[11]  L. Nafie,et al.  Ring current mechanism of vibrational circular dichroism , 1986 .

[12]  D. Klug,et al.  Effect of hydrogen bonding on the direction of the dipole‐moment derivative of the O–H bond in the water molecule , 1986 .

[13]  L. Nafie,et al.  Enhanced vibrational circular dichroism via vibrationally generated electronic ring currents , 1985 .

[14]  P. Stephens.  Theory of vibrational circular dichroism , 1985 .

[15]  M. Moskovits,et al.  Vibrational circular dichroism: effect of charge fluxes and bond currents , 1982 .

[16]  S. Abbate,et al.  A charge flow model for vibrational rotational strengths , 1981 .

[17]  R. Kuroda,et al.  The crystal and molecular structure of R-(–)-1,1′-binaphthyl: the conformational isomerism and a comparison of the chiral with the racemic packing mode , 1981 .

[18]  I. Paul,et al.  Solid-state resolution of binaphthyl: crystal and molecular structures of the chiral (A)1 form and racemic (B)1 form and the study of the rearrangement of single crystals. Requirements for development of hemihedral faces for enantiomer identification , 1980 .

[19]  C. J. Barnett,et al.  A dynamic polarization model for vibrational optical activity and the infrared circular dichroism of a dihydro[5]helicene , 1980 .

[20]  C. J. Barnett,et al.  Optical activity of characteristic vibrational modes and absolute configuration , 1980 .

[21]  O. E. Weigang,et al.  An amplified sector rule for electric dipole-allowed transitions , 1979 .

[22]  T. R. Faulkner,et al.  Infrared circular dichroism associated with the C-H strecthing vibration of tartaric acid , 1976 .

[23]  P. Stephens,et al.  Vibrational Circular Dichroism , 1976 .

[24]  J. Schellman.  Erratum: Vibrational optical activity , 1974 .

[25]  J. Schellman.  Vibrational optical activity , 1973 .

[26]  I. Chabay,et al.  Optical Activity of Vibrational Transitions: A Coupled Oscillator Model , 1972 .

[27]  I. Hanazaki,et al.  Optical rotatory power of 2,2'-dihydroxy-1,1'-binaphthyl and related compounds , 1972 .

[28]  A. Moscowitz,et al.  Optical Activity of Vibrational Origin. II. Consequences of Polymer Conformation , 1970 .

[29]  A. Moscowitz,et al.  Optical Activity of Vibrational Origin. I. A Model Helical Polymer , 1968 .

[30]  O. E. Weigang,et al.  Electron Correlation Models for Optical Activity , 1968 .

[31]  L. Radom,et al.  Molecular polarisability. Carbon–carbon bond polarisabilities in relation to bond lengths , 1967 .

[32]  P. Schleyer,et al.  Hydrogen Bonding in ortho-Substituted Biphenyls1 , 1965 .