Fascination with the conformational analysis of succinic acid, as evaluated by NMR spectroscopy, and why

Accounts of Chemical Research

Volumn 39, Issue 12, 2006, Pages 889-896

  Roberts, John D ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SUCCINIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SUCCINIC ACID;

EID: 33846221468     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar050229p     Document Type: Article

References (62)

1. A. W. Hofmann made ball-and-stick models out of croquet balls and sticks, but the balls were positioned in one plane to correspond to the structures he wrote on paper, 1865.
2. Heyden, J. The History of Chemistry; Chapman and Hall: New York, 1992; p 139.
3. Paterno, E. Intorno all'azione del percloruro di fosforo sul clorale. G. Sci. Econ. Palermo 1869, 5, 117-122.
4. Brescia, F.; Manglaracina, P. Conformational Analysis, 1869. J. Chem. Educ. 1976, 53, 32-33.
5. Bischoff, C. Ueber die Aufhebubg der frien Drehbarkeit von verbundenen Kohlenstoffatomen. Chem. Ber. 1890, 23, 623-669.
6. Bischoff, C. A. Die Dynamische Hypothese ihrer Anwendund auf Bernsteinsauregruppe. Chem. Ber. 1891, 24, 1085-1095.
7. Bykov, C. A. In van't Hoff-Le Bel Centenial; Ramsay, O. B., Ed.; American Chemical Society: Washington, DC, 1974; pp 114-122.
8. Hassel, O. Structural Aspects of Interatomic Charge-Transfer Bonding; Elsevier Publishing: Amsterdam, 1972.
9. Barton, D. H. R. The Principles of Conformational Analysis; Elsevier Publishing: Amsterdam, 1972.
10. Pitzer, K. S.; Kemp, J. D. The Entropy of Ethane and the Third Law of Thermodynamics. Hindered Rotation of Methyl Groups. J. Am. Chem. Soc. 1937, 55, 276-279.
11. Schreiner, P. R. Teaching the Right Reasons: Lessons from the Mistaken Origin of the Rotational Barrier in Ethane. Angew. Chem., Int. Ed. 2002, 41, 3579-3582.
12. Bickelhaupt, F. M.; Baerends, E. J. The Case for Steric Repulsion Causing the Staggered Conformation of Ethane. Angew. Chem., Int. Ed. 2003, 42, 4183-4188.
13. Newman, M. S. A Notation for the Study of Certain Stereochemical Problems. J. Chem. Educ. 1955, 32, 344.
14. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science books: Sausalito, CA, 2005; pp 92-99.
15. Eliel, E. L. Conformational Analysis; Interscience: New York, 1965.
16. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley & Sons: New York, 1994; pp 606-615.
17. Eliel, E. L.; Wilen, S. H.; Doyle, M. P. Basic Organic Stereochemistry; Wiley-Interscience: New York, 2001.
18. Nair, P. M.; Roberts, J. D. Nuclear Magnetic Resonance Spectra. Hindered Rotation and Molecular Asymmetry. J. Am. Chem. Soc. 1957, 79, 468-469.
19. Roberts, J. D. Nuclear Magnetic Resonance; McGraw-Hill: New York, 1959, pp 71-74.
20. McDaniel, D. H.; Brown, H. C. Hydrogen Bonding as a Factor in the Ionization of Dicarboxylic Acids. Science 1953, 118, 370-372.
21. Brown, H. C.; McDaniel, D. H.; Häflinger, O. Determination of Organic Structures by Physical Methods; Academic Press: New York, 1955; pp 622-634.
22. Kirkwood, J. G.; Westheimer, F. H. The Electrostatic Influence of Substituents on the Dissociation Constants of Organic Acids. I. J. Chem. Phys. 1938, 6, 506-512.
23. Westheimer, F. H.; Benfey, O. T. Quantitative Evaluation of the Effect of Hydrogen Bonding on the Strength of Dibasic Acids. J. Am. Chem. Soc. 1956, 78, 5309-5311.
24. Westheimer, F. H.; Kirkwood, J. G. The Electrostatic Influence of Substituents on the Dissociation Constants of Organic Acids. II J. Chem. Phys. 1938, 6, 513-517.
25. Bothner-By, A. A.; Castellano, S. M. Computer Programs for Chemistry; W. A. Benjamin, Inc.: New York, 1968; pp 10-53.
26. gNMR 4.1, I., Adept Scientific: Litchworth, Herbs, 1999.
27. Altona, C.; Francke, R.; Haan, R. d.; Ippel, J. H.; J. Daalmans, G.; Hoekzema, A. J. A. W.; Wijk, J. v. Empirical Group Electronegativities for Vicinal NMR Proton-Proton Couplings Along a C-C Bond: Solvent Effects and Reparameterization of the Haasnoot Equation Magn. Reson. Chem. 1994, 32, 670-678.
28. Gregoire, F.; Wei, S. H.; Streed, E. W.; Brameld, K. A.; Fort, D.; Hanely, L. J.; Walls, J. D.; Goddard, W. A.; Roberts, J. D. Conformational Equilibria Of b-Alanine And Related Compounds As Studied By Nmr Spectroscopy. J. Am. Chem. Soc. 1998, 120, 7337-7343.
29. Rudner, M. S.; Kent IV, D. R.; Goddard, W. A. I.; Roberts, J. D. Intramolecular Hydrogen Bonding in Disubstituted Ethanes: General Considerations and Methodology in Quantum Mechanical Calculations of the Conformational Equilibria of Succinamate Monoanion. J. Phys. Chem. A 2005, 109, 9083-9088.
30. Lit, E. S.; Mallon, F. K.; H. Y., T.; Roberts, J. D. Conformational Changes of Butanedioic Acid as a Function of pH as Determined from Changes in Vicinal Proton-Proton Coupling Constants. J. Am. Chem. Soc. 1993, 115, 9563-9567.
31. Nunes, T.; Gil, V. M. S.; Ascenso, J. The Conformation of Succinic Acid in Aqueous Solution Studied by Proton and Carbon-13 NMR. Tetrahedron 1981, 37, 611-614.
32. Price, D. J.; Roberts, J. D.; Jorgenson, W. L. Conformational Complexity of Succinic Acid and its Monoanion in the Gas Phase and in Solution: Ab Initio Calculations and Monte Carlo Simulations. J. Am. Chem. Soc. 1998, 120, 9672-9679.
33. Gandour, R. D. On the Importance of Orientation in General Base Catalysis by Carboxylate. Bioorg. Chem. 1981, 169-176.
34. Jung, M. E.; Gervay, J. A New NMR Technique for measuring the Ground State Populations of Formate Esters: Polar Aprotic Sovents Favor the s-cis (E)-Isomer of t-Butyl Formate. Tetrahedron Lett. 1990, 31, 4685-4688.
35. Gitlin, I.; Carbeck, J. D.; Whitesides, G. M. Why are Proteins Charged? Networks of Charge-Charge Interactions in Proteins Measured ny Charge Ladders and Capillary Electrophoresis. Angew. Chem., Int. Ed. 2006, 45, 3022-3060.
36. Kunz, W.; Belloni, L.; Bernard, O.; Ninham, B. W. Osmotic Coefficients and Surface Tensions of Aqueous Electrolyte Solutions: Role of Dispersion Forces. J. Phys. Chem. B 2004, 108, 2398-2404.
37. Perrin, C. L.; Thoburn, J. D. Symmetries of Hydrogen Bonds in Monoanions of Dicarboxylic Acids. J. Am. Chem. Soc. 1992, 114, 8559-8569.
38. Williams, L. N.; Petterson, K. A.; Roberts, J. D. The Conformations of 1,4-Butanedioic Acid as a Function of Solvent Polarity in a Series of Alcohols as Determined by NMR Spectroscopy. J. Phys. Chem. A 2002, 106, 7491-7943.
39. Woertink, J. K. Unpublished work, 2003.
40. Pachler, K. G. R.; Wessels, P. L. Rotational Isomerism - X. A Nuclear Magnetic Resonance Study of 2-Fluoroethanol and Ethylene Glycol. J. Mol. Struc. 1970, 6, 471-478.
41. Wiberg, K. B.; Keith, T. A.; Frisch, M. J.; Murcko, M. A. Solvent Effects on 1,2-Dihaloethane Gauche/Trans Ratios. J. Chem. Phys. 1995, 99, 9072-9079.
42. Kent IV, D. R.; Dey, N.; Davidson, F.; Gregoire, F.; Goddard, W. A., III; Roberts, J. D. An NMR and Quantum Mechanical Investigation of Solvent Effects on Conformational Equilibria of Butanedinitrile. J. Am. Chem. Soc. 2002, 124, 9318-9322.
43. Petterson, K. A.; Stein, R. S.; Drake, M. D.; Roberts, J. D. An NMR Investigation of the Importance of Intramolecular Hydrogen Bonding in Determining the Conformational Equilibrium of Ethylene Glycol in Solution. Magn. Res. Chem. 2005, 43, 225-230.
44. Griffith, R. C.; Roberts, J. D. The Question of Intramolecular Hydorgen Bonding in 2-Fluoroethanol. Tetrahedron Lett. 1974, 3499-3502.
45. Abraham, R. J.; Smith, T. A. D.; Thomas, W. A. Conformational Analysis. Part 28. OH⋯F Hydrogen Bonding and the Conformation of trans-2-Fluorocyclohexanol. J. Chem. Soc., Perkin Trans. 2 1996, 1949-1955.
46. Freitas, M. P.; Tormena, C. F.; Rittner, R.; Abraham, R. J. Conformational Analysis of trans-2-Halocyclohexanols and Their Methyl Ethers. J. Phys. Org. Chem. 2003, 16, 27-33.
47. Freitas, M. P.; Tormena, C. F.; Rittner, R.; Abraham, R. J. Conformational Properties of trans-2-Halo-acetoxycyclohexanes: 1H NMR, Solvation and Theoretical Investigation. J. Mol. Struct. 2005, 734, 211-217.
48. Brunck, T. K.; Weinhold, F. J. Quantum-Mechanical Studies on the Origin of Barriers to Internal Rotation about Single Bonds. J. Am. Chem. Soc. 1979, 101, 1700-1709.
49. Goodman, L.; Gu, H.; Pophristic, V. J. Gauche Effect in 1,2-Difluoroethane. Hyperconjugation, Bent Bonds, Steric Repulsion. J. Phys. Chem. A 2005, 109, 1223-1229.
50. Abraham, R. J.; Gatti, G. Rotational Isomerism. VII. Effect of Substituents on Vicinal Coupling Constants in XCH2-CH2Y Fragments. J. Chem. Soc. B 1969, 961-968.
51. Kolthoff, I. M.; Chantooni, J., M. K. Intramolecular Hydrogen Bonding Involving Hydroxyl Groups in Mono- and Dianions of Diprotic Acids in Acetonitrile and Dimethyl Sulfoxide. J. Am. Chem. Soc. 1976, 98, 5063-5068.
52. Kolthoff, I. M.; Chantooni, J., M. K. Titration of Diprotic Acids in Alcohols and Intramolecular Hydrogen Bonding in Monoanions with Emphasis on Isopropanol and tert-Butanol. Anal. Chem. 1978, 50, 1440-1446.
53. Perrin, C. L.; Fabian, M. A. Multicomponent NMR. Titration for Simultaneous Measurement of Relative pKs. Anal. Chem. 1996, 68, 2127-2134.
54. Choi, P. J.; Petterson, K. A.; D., R. J. Ionization Equilibria of Dicarboxylic Acids in Dimethyl Sulfoxide as Studied by NMR. J. Phys. Org. Chem. 2002, 15, 278-286.
55. Bordwell, F. G. Equilibrium Acidities in Dimethyl Sulfoxide Solution. Acc. Chem. Res. 1988, 21, 456-463.
56. Born, M. Volumen und Hydrationswarme der Ionen. Z. Phyz. 1920, 1, 45.
57. Kent IV, D. R.; Petterson, K. A.; Gregoire, F.; Snyder-Frey, E.; Hanely, L. J.; Muller, R. P.; Goddard, W. A.; Roberts, J. D. An NMR and Quantum-Mechanical Investigation of Tetrahydrofuran Solvent Effects on the Conformational Equilibria of 1, 4-Butanedioic Acid Salts. J. Am. Chem. Soc. 2002, 124, 4481-4486.
58. Altona, C.; Francke, R.; de Haan, R.; Ippel, J. H.; Daalmans, G. J.; Westra Hoekzema, A. J. A.; van Wijk, J. Empirical Group Electronegativities for Vicinal NMR Proton-Proton Couplings along a C-C Bond: Solvent Effects and Reparameterization of the Haasnoot Equation. Magn. Reson. Chem. 1994, 32, 670-678.
59. Chidichimo, G.; Imbardelli, D.; Longeri, M.; Saupe, A. Conformation of Ethylene Glycol Dissolved in a Nematic-Lyotropic Solution: An NMR Analysis. Mol. Phys. 1988, 65, 1143-1151.
60. Chidichimo, G.; Formoso, P.; Golemme, A.; Imbardelli, D. Conformation of Succinic Acid: Its pH Dependence by Liquid-Crystal-Mesophase (Licry)-NMR Analysis. Mol. Phys. 1993, 79, 25-38.
61. Džakula, Ž.; Westler, W. M.; Edison, A. S.; Markley, J. L. The "CUPID" Method for Calculating the Continuous Probability Distribution of Rotamers from NMR Data. J. Am. Chem. Soc. 1992, 114, 6195-6199
62. 1 Rotamer Populations from NMR Data by the CUPID Method. J. Am. Chem. Soc. 1992, 114, 6200-6209.