Conformational analyses of 2,3-dihydroxypropanoic acid as a function of solvent and ionization state as determined by NMR spectroscopy
Vicinal 1H1H coupling constants were used to determine the conformational preferences of 2,3‐dihydroxypropanoic acid (1) (DL‐glyceric acid) in various solvents and its different carboxyl ionization states. The stereospecific assignments of J12 and J13 were confirmed through the point‐group substitu...
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| Published in | Magnetic resonance in chemistry Vol. 44; no. 3; pp. 210 - 219 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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Chichester, UK
John Wiley & Sons, Ltd
01.03.2006
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| Abstract | Vicinal 1H1H coupling constants were used to determine the conformational preferences of 2,3‐dihydroxypropanoic acid (1) (DL‐glyceric acid) in various solvents and its different carboxyl ionization states. The stereospecific assignments of J12 and J13 were confirmed through the point‐group substitution of the C‐3 hydrogen with deuterium, yielding rac‐(2SR,3RS)‐[3‐2H]‐1, and the observation of only J13 in the 1H NMR spectra. While hydrogen bonding and steric strain may be expected to drive the conformational equilibrium, their role is overshadowed by a profound gauche effect between the vicinal hydroxyl groups that mimics other substituted ethanes, such as 1,2‐ethanediol and 1,2‐difluoroethane. At low pH, the conformational equilibrium is heavily weighted toward the gauche‐hydroxyl rotamers with a range of 81% in DMSO‐d6 to 92% in tert‐butyl alcohol‐d10. At high pH, the equilibrium exhibits a larger dependence upon the polarity and solvating capability of the medium, although the gauche effect still dominates in D2O, 1,4‐dioxane‐d8, methanol‐d4, and ethanol‐d6 (96, 89, 85, and 83% gauche‐hydroxyls respectively). The observed preference for the gauche‐hydroxyl rotamers is believed to stem primarily from hyperconjugative σCH → σ*COH interactions. Copyright © 2006 John Wiley & Sons, Ltd. |
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| AbstractList | Vicinal 1H1H coupling constants were used to determine the conformational preferences of 2,3‐dihydroxypropanoic acid (1) (DL‐glyceric acid) in various solvents and its different carboxyl ionization states. The stereospecific assignments of J12 and J13 were confirmed through the point‐group substitution of the C‐3 hydrogen with deuterium, yielding rac‐(2SR,3RS)‐[3‐2H]‐1, and the observation of only J13 in the 1H NMR spectra. While hydrogen bonding and steric strain may be expected to drive the conformational equilibrium, their role is overshadowed by a profound gauche effect between the vicinal hydroxyl groups that mimics other substituted ethanes, such as 1,2‐ethanediol and 1,2‐difluoroethane. At low pH, the conformational equilibrium is heavily weighted toward the gauche‐hydroxyl rotamers with a range of 81% in DMSO‐d6 to 92% in tert‐butyl alcohol‐d10. At high pH, the equilibrium exhibits a larger dependence upon the polarity and solvating capability of the medium, although the gauche effect still dominates in D2O, 1,4‐dioxane‐d8, methanol‐d4, and ethanol‐d6 (96, 89, 85, and 83% gauche‐hydroxyls respectively). The observed preference for the gauche‐hydroxyl rotamers is believed to stem primarily from hyperconjugative σCH → σ*COH interactions. Copyright © 2006 John Wiley & Sons, Ltd. Vicinal (1)H--(1)H coupling constants were used to determine the conformational preferences of 2,3-dihydroxypropanoic acid (1) (DL-glyceric acid) in various solvents and its different carboxyl ionization states. The stereospecific assignments of J(12) and J(13) were confirmed through the point-group substitution of the C-3 hydrogen with deuterium, yielding rac-(2SR,3RS)-[3-(2)H]-1, and the observation of only J(13) in the (1)H NMR spectra. While hydrogen bonding and steric strain may be expected to drive the conformational equilibrium, their role is overshadowed by a profound gauche effect between the vicinal hydroxyl groups that mimics other substituted ethanes, such as 1,2-ethanediol and 1,2-difluoroethane. At low pH, the conformational equilibrium is heavily weighted toward the gauche-hydroxyl rotamers with a range of 81% in DMSO-d(6) to 92% in tert-butyl alcohol-d(10). At high pH, the equilibrium exhibits a larger dependence upon the polarity and solvating capability of the medium, although the gauche effect still dominates in D(2)O, 1,4-dioxane-d(8), methanol-d(4), and ethanol-d(6) (96, 89, 85, and 83% gauche-hydroxyls respectively). The observed preference for the gauche-hydroxyl rotamers is believed to stem primarily from hyperconjugative sigma(C--H) --> sigma*(C--OH) interactions. Vicinal 1 H 1 H coupling constants were used to determine the conformational preferences of 2,3‐dihydroxypropanoic acid (1) (DL‐glyceric acid) in various solvents and its different carboxyl ionization states. The stereospecific assignments of J 12 and J 13 were confirmed through the point‐group substitution of the C‐3 hydrogen with deuterium, yielding rac ‐(2 SR ,3 RS )‐[3‐ 2 H]‐1, and the observation of only J 13 in the 1 H NMR spectra. While hydrogen bonding and steric strain may be expected to drive the conformational equilibrium, their role is overshadowed by a profound gauche effect between the vicinal hydroxyl groups that mimics other substituted ethanes, such as 1,2‐ethanediol and 1,2‐difluoroethane. At low pH, the conformational equilibrium is heavily weighted toward the gauche‐hydroxyl rotamers with a range of 81% in DMSO‐ d 6 to 92% in tert ‐butyl alcohol‐ d 10 . At high pH, the equilibrium exhibits a larger dependence upon the polarity and solvating capability of the medium, although the gauche effect still dominates in D 2 O, 1,4‐dioxane‐ d 8 , methanol‐ d 4 , and ethanol‐ d 6 (96, 89, 85, and 83% gauche‐hydroxyls respectively). The observed preference for the gauche‐hydroxyl rotamers is believed to stem primarily from hyperconjugative σ CH → σ* COH interactions. Copyright © 2006 John Wiley & Sons, Ltd. Vicinal (1)H--(1)H coupling constants were used to determine the conformational preferences of 2,3-dihydroxypropanoic acid (1) (DL-glyceric acid) in various solvents and its different carboxyl ionization states. The stereospecific assignments of J(12) and J(13) were confirmed through the point-group substitution of the C-3 hydrogen with deuterium, yielding rac-(2SR,3RS)-[3-(2)H]-1, and the observation of only J(13) in the (1)H NMR spectra. While hydrogen bonding and steric strain may be expected to drive the conformational equilibrium, their role is overshadowed by a profound gauche effect between the vicinal hydroxyl groups that mimics other substituted ethanes, such as 1,2-ethanediol and 1,2-difluoroethane. At low pH, the conformational equilibrium is heavily weighted toward the gauche-hydroxyl rotamers with a range of 81% in DMSO-d(6) to 92% in tert-butyl alcohol-d(10). At high pH, the equilibrium exhibits a larger dependence upon the polarity and solvating capability of the medium, although the gauche effect still dominates in D(2)O, 1,4-dioxane-d(8), methanol-d(4), and ethanol-d(6) (96, 89, 85, and 83% gauche-hydroxyls respectively). The observed preference for the gauche-hydroxyl rotamers is believed to stem primarily from hyperconjugative sigma(C--H) --> sigma*(C--OH) interactions. |
| Author | Roberts, John D. Drake, Michael D. Terterov, Sergei Harsha, Alex K. |
| Author_xml | – sequence: 1 givenname: Michael D. surname: Drake fullname: Drake, Michael D. organization: Gates and Crellin Laboratories of Chemistry, California Institute of Technology, Pasadena, California 91125, USA – sequence: 2 givenname: Alex K. surname: Harsha fullname: Harsha, Alex K. organization: Gates and Crellin Laboratories of Chemistry, California Institute of Technology, Pasadena, California 91125, USA – sequence: 3 givenname: Sergei surname: Terterov fullname: Terterov, Sergei organization: Gates and Crellin Laboratories of Chemistry, California Institute of Technology, Pasadena, California 91125, USA – sequence: 4 givenname: John D. surname: Roberts fullname: Roberts, John D. email: robertsj@caltech.edu organization: Gates and Crellin Laboratories of Chemistry, California Institute of Technology, Pasadena, California 91125, USA |
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| Snippet | Vicinal 1H1H coupling constants were used to determine the conformational preferences of 2,3‐dihydroxypropanoic acid (1) (DL‐glyceric acid) in various... Vicinal (1)H--(1)H coupling constants were used to determine the conformational preferences of 2,3-dihydroxypropanoic acid (1) (DL-glyceric acid) in various... Vicinal 1 H 1 H coupling constants were used to determine the conformational preferences of 2,3‐dihydroxypropanoic acid (1) (DL‐glyceric acid) in various... |
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| SubjectTerms | 1H NMR 2,3‐dihydroxypropanoic acid 3-dihydroxypropanoic acid conformational analysis gauche effect glyceric acid glyceric acid deuteriation hyperconjugation NMR solvent effects |
| Title | Conformational analyses of 2,3-dihydroxypropanoic acid as a function of solvent and ionization state as determined by NMR spectroscopy |
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