Scalar coupling across the hydrogen bond in 1,3- and 1,4-diols

Organic Letters

Volumn 2, Issue 14, 2000, Pages 2077-2080

  Fierman, Matthew ^a   Nelson, Alshakim ^a   Khan, Saeed I ^b   Barfield, Michael ^a,c   O'Leary, Daniel J ^a  

^a POMONA COLLEGE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN CONFORMATION; X RAY DIFFRACTION;

ALCOHOLS; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION; PROTEIN CONFORMATION; X-RAY DIFFRACTION;

EID: 0034644008     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0060679     Document Type: Article

References (28)

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2. hxJ, where x designates the number of bonds separating the coupling nuclei.
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4. (b) Cordier, F.; Grzesiek, S. J. Am. Chem. Soc. 1999, 121, 1601-1602.
5. (c) Cornilescu, G.; Hu, J.-S.; Bax, A. J. Am. Chem. Soc. 1999, 121, 2949-2950.
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11. For a recent study of hydrogen bonding in the water dimer and ice, see: Ghanty, T. K.; Staroverov, V. N.; Koren, P. R.; Davidson, E. R. J. Am. Chem. Soc. 2000, 122, 1210-1214.
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14. The synthesis of diol 2 will be described in a separate paper.
15. Two conformers, differing in the orientation of the secondary hydroxyl group, occupy the unit cell (Table 1). The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre.
16. 1. Experiment time: 190 min.
17. Bax, A. Two-Dimensional Nuclear Magnetic Resonance in Liquids; Delft University Press: Delft, 1982.
18. 6 and molecular weight of diol 2, it is very likely that the deuterium spin states are sufficiently short-lived so as to provide spontaneous deuterium decoupling.
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20. 2. See ref 15.
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22. 1): 2.69 Hz/pt, 256 FIDs recorded, each consisting of 8 scans and 1024 data points. Processing parameters: unshifted sinusoidal apodization was applied in both dimensions prior to the Fourier transform. Experiment time: 70 min.
23. Diol 5 was synthesized according to an established procedure: Cookson, R. C.; Crundwell, E.; Hill, R. R.; Hudec, J. J. Chem. Soc. 1964, 3062-3075.
24. Structures were optimized at the MP2/6-31G* level of theory using Gaussian 94/98.
25. The Fermi contact contributions to the scalar coupling constants were based on finite perturbation theory and were obtained from Gaussian 94 via the FIELD option. All coupling constants were computed by using the unrestricted DFT UB3PW91/6-311G** triple-split level with polarization functions on hydrogens and heavier elements. See: Onak, T.; Jaballas, J.; Barfield, M. J. Am. Chem. Soc. 1999, 121, 2850-.
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