Extension of the Karplus relationship for NMR spin-spin coupling constantsto nonplanar ring systems: Pseudorotation of tetrahydrofuran

International Journal of Molecular Sciences

Volumn 4, Issue 4, 2003, Pages 158-192

  Wu, Anan ^a   Cremer, Dieter ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

Karplus relationship; NMR spin spin coupling constants; Ribose; Ring puckering; Tetrahydrofuran

Indexed keywords

RIBOSE; TETRAHYDROFURAN;

ARTICLE; COMPARATIVE STUDY; CONFORMATION; COVALENT BOND; DENSITY FUNCTIONAL THEORY; ELECTRON SPIN RESONANCE; ENTHALPY; FOURIER ANALYSIS; GEOMETRY; NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY;

ENTEROBACTERIA PHAGE P1D;

EID: 0242384289     PISSN: 14220067     EISSN: None     Source Type: Journal    
DOI: 10.3390/i4040158     Document Type: Article

References (71)

1. Grant, D. M.; Harris, R. K., Edt.s, Encyclopedia of Nuclear Magnetic Resonance; Wiley: Chichester, UK, 1996, Vol 1-8.
2. Kowalewski, J. Calculations of Nuclear Spin-Spin Coupling Constants. Prog. NMR Spectrosc. 1977, 11, 1-78.
3. Kowalewski, J. Calculations of Nuclear Spin-Spin Couplings. Ann. Rep. NMR Spectrosc. 1982, 12, 81-176.
4. Contreras, R. H.; Facelli, J. C. Advances In Theoretical Physical Aspects of Spin-Spin Coupling Constants. Ann. Rep. NMR Spectrosc. 1993, 27, 255-356.
5. Contreras, R. H.; Peralta, J. E. Angular Dependence of Spin-Spin Coupling Constabts. Prog NMR Spectrosc. 2000, 37, 321-425.
6. Karplus, M.; Anderson, D. H. Valence-Bond Interpretation of Electron-Coupled Nuclear Spin Interactions; Application to Methane. J. Chem. Phys. 1959, 30, 6-10.
7. Karplus, M. Contact Electron-Spin Coupling of Nuclear Magnetic Moments. J. Chem. Phys. 1959, 30, 11-15.
8. Karplus, M. Vicinal Proton Coupling in Nuclear Magnetic Resonance. J. Am. Chem. Soc. 1963, 85, 2870-2871.
9. Altona, C. in Encyclopedia of Nuclear Magnetic Resonance, Grant, D. M.; Harris, R. K., Edt.s, Wiley:Chichester, UK, 1996, p. 4909.
10. Altona, C.; Sundaralingam, M. Conformational Analysis of the Sugar Ring in Nucleosides and Nucleotides. Improved Method for the Interpretation of Proton Magnetic Resonance Coupling Constants. J. Am. Chem. Soc. 1973, 95, 2333-2344.
11. Haasnoot, C. A. G. Conformational Analysis of Six-Membered Rings in Solution: Ring Puckering Coordinates Derived from Vicinal NMR Proton-Proton Coupling Constants. J. Am. Chem. Soc. 1993, 115, 1460-1468.
12. Wu, A. A.; Cremer, D.; Auer, A. A.; Gauss, J. Extension of the Karplus Relationship for NMR Spin-Spin Coupling Constants to Nonplanar Ring Systems: Pseudorotation of Cyclopentane. J. Phys. Chem. A 2002, 106, 657-667.
13. Sychrovsky, V.; Gräfenstein, J.; Cremer, D. Nuclear Magnetic Resonance Spin-Spin Coupling Constants From Coupled Perturbed Density Functional Theory. J. Chem. Phys. 2000, 113, 3530-3547.
14. For a review on the calculation of SSCCs, see Helgaker, T.; Jaszunski, M.; Ruud, K. Ab Initio Methods for the Calculation of NMR Shielding and Indirect Spin-Spin Coupling Constants. Chem. Rev. 1999, 99, 293-352, and references cited therein.
15. Gauss, J.; Stanton, J. F. Analytic CCSD(T) Second Derivatives. Chem. Phys. Letters 1997, 276, 70-77.
16. Szalay, P. G.; Gauss, J.; Stanton, J. F. Analytic UHF-CCSD(T) Second Derivatives. Implementation and Application to the Calculation of the Vibration-Rotation Interaction Constants of NCO and NCS. Theoret. Chem. Acc. 1998, 100, 5-11.
17. Auer, A. A.; Gauss, J. Triple Excitation Effects in Coupled-Cluster Calculations of Indirect Spin-Spin Coupling Constants. J. Chem. Phys. 2001, 115 1619-1622.
18. Lafferty, W. J.; Robinson, D. W.; Louis, R. V. St.; Russell, J. W.; Strauss, H. L. Far-Infrared Spectrum of Tetrahydrofuran: Spectroscopic Evidence for Pseudorotation. J. Chem. Phys. 1965, 42, 2915-2919.
19. Davidson, R.; Warsop, P. A. Energy Levels for Pseudorotation and Their Application to Cyclopentane, Tetrahydrofuran, and 1,3-Dioxolane. J. Chem. Soc. Faraday Trans II 1972, 68, 1875-1889.
20. Engerholm, G. G.; Luntz, A. C.; Gwinn, W. D.; Harris, D. O. Ring Puckering in Five-Membered Rings.II. The Microwave Spectrum, Dipole Moment, and Barrier to Pseudorotation in Tetrahydrofuran. J. Chem. Phys. 1969, 50, 2446-2457.
21. Meyer, R.; Lopez, J. C.; Alonso, J. L.; Melandri, S.; Favero, P. G.; Caminati, W. Pseudorotation Pathway and Equilibrium Structure ¿From the Rotational Spectrum of Jet-cooled Tetrahydrofuran. J. Chem. Phys. 1999, 111, 7871-7880.
22. Geise, H. J.; Adams, W. J.; Bartell, L. S. Electron Diffraction Study of Gaseous Tetrahydrofuran. Tetrahedron 1969, 25, 3045-3052.
23. Luger, P.; Buschmann, J. Twist Conformation of Tetrahydrofuran in the Crystal Form. Angew. Chem. 1983, 95, 423-424.
24. David, W. I. F.; Ibberson, R. M. A Reinvestigation of the Structure of Tetrahydrofuran by High-Resolution Neutron Powder Diffraction. Acta Crystallogr., Sect. C 1992, 48, 301-303.
25. Cremer, D.; Pople, J. A. Molecular Orbital Theory of the Electronic Structure of Organic Compounds. XXIII. Pseudorotation in Saturated Five-Membered Ring Compounds. J. Am. Chem. Soc. 1975, 97, 1358-1367.
26. Han, S. J.; Kang, Y. K. Pseudorotation in Heterocyclic Five-Membered Rings: Tetrahydrofuran and Pyrrolidine. J. Mol. Struc. (Theochem) 1996, 369, 157-165.
27. Diez, E.; Palma, J.; San-Fabián, J.; Guilleme, J. Effect of the Substituents on the Conformational Behavior of Five-Membered Rings: Application to cis- and trans-2,5-Dimethoxytetrahydrofuran. J. Comp. Chem. 1988, 9, 189-199.
28. Siri, D.; Gaudel, A.; Tordo, P. Conformational Analysis of Five-Membered Rings by Molecular Mechanics: Application to Nitroxides. Theochem. 2002, 582, 171-185.
29. Lambert, J. B.; Papay, J. J.; Khan, S. A.; Kappauf, K. A.; Magyar, E. S. Conformational Analysis of Five-Membered Rings. J. Am. Chem. Soc. 1974, 96, 6112-6118.
30. 13C-NMR- Spektroskopie, Thieme: Stuttgart, 1984.
31. Church, T. J.; Carmichael, I.; Serianmi, A. S. 13C-1H and 13C-13C Spin-Coupling Constants in Methyl β-D-Ribofuranoside and Methyl 2-Deoxy-β-D-erythro-pentofuranoside: Correlations with Molecular Structure and Conformation. J. Am. Chem. Soc. 1997, 119, 8946-8964.
32. Jaworski, A.; Ekiel, I.; Shugar, D. Coupling Constants between Cisoidal Protons in Pentose Nucleosides. Limitations of Range of Application of Karplus Relation, and Solution Conformations of β-arabinofuranosyl and β-xylofuranosyl Nucleosides. J. Am. Chem. Soc. 1978, 100, 4357-4361.
33. Jaworski, A.; Ekiel, I. Calculations of Proton NMR Coupling Constants for Conformational Studies of Isomeric Pentofuranosyl Nucleosides. Int. J. Quant. Chem. 1979, 16, 615-622.
34. Cremer, D.; Pople, J. A. General Definition of Ring Puckering Coordinates. J. Am. Chem. Soc. 1975, 97, 1354-1358.
35. Cremer, D.; Szabo, K. J. Methods in Stereochemical Analysis, Conformational Behavior of Six-Membered Rings, Analysis, Dynamics, and Stereoelectronic Effects, E. Juaristi, Edt., VCH Publishers, 1995, 59-135.
36. Cremer, D. A General Definition of Ring Substituent Positions. Israel J. Chem. 1980, 20, 12-19.
37. Cremer, D. Calculation of Puckered Rings With Analytical Gradients. J. Phys. Chem. 1990, 94, 5502-5509.
38. Cremer, D. On the Correct Usage of the Cremer-Pople Puckering Parameters as Quantitative Descriptors of Ring Shapes - A Reply to Recent Criticism by Petit, Dillen and Geise. Acta Cryst. B 1984, 40, 498-500.
39. Essen, H.; Cremer, D. On the Relationship between the Mean Plane and the Least-squares Plane of an N-Membered Puckered Ring. Acta Cryst. B 1984, 40, 418-420.
40. Cremer, D. Theoretical Determination of Molecular Structure and Conformation. XI. the Puckering of Oxolanes. Isr. J. Chem., 1983, 23, 72-84.
41. Cremer, D. Theoretical Determination of Molecular Structure and Conformation. J. Chem. Phys. 1979, 70, 1898-1910; 1911-1927; 1928-1938.
42. Stoddard, J. F, Stereochemistry of Carbohydrates, Wiley-Interscience: New York, 1971.
43. For a recent review see, Cremer, D. Møller-Plesset Perturbation Theory In: Encyclopedia of Computational Chemistry Schleyer, P. v R.; Allinger, N. L.; Clark, T.; Gasteiger, J.; Kollman, P. A.; Schaefer, H. F.; Schreiner, P. R.; Edt.s, Wiley: Chichester UK, Vol 3, 1706.
44. Dunning Jr, T. H. Gaussian Basis Sets for Use in Correlated Molecular Calculations. I. the Atoms boron through Neon and Hydrogen. J. Chem. Phys. 1989, 99, 1007-1023.
45. Kohn, W.; Sham, L. J. Quantum Density Oscillations in an Inhomogeneous Electron Gas. Phys. Rev. 1965, 137, 1697-1705.
46. For a review on DFT, see, e.g., Parr, R. G.; Yang, W. International Series of Monographs on Chemistry 16: Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
47. Becke, A. D. Density-Functional Thermochemistry. III. the Role of Exact Exchange. J. Chem. Phys. 1993, 98, 5648-5652.
48. Becke, A. D. Density-Functional Exchange-Energy Approximation With Correct Asymptotic Behavior. Phys. Rev. A 1988, 38, 3098-3100.
49. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density. Phys. Rev. B 1988, 37, 785-789.
50. Hariharan, P. C.; Pople, J. A. Influence of Polarization Functions on MO Hydrogenation Energies. Theoret. Chim. Acta 1973, 28, 213-222.
51. McQuarrie, D. A. Statistical Thermodynamics, Harper and Row Publishers: New York, 1973.
52. Kraka, E.; Gauss, J.; Cremer, D. Determination and Use of Response Densities. J. Mol. Struct. THEOCHEM 1991, 80, 95-126.
53. Gauss, J.; Cremer, D. Analytical Energy Gradients in Møller- Plesset Perturbation and Quadratic Configuration Interaction Methods: Theory and Application. Adv. Quantum Chem. 1992, 23, 205-299.
54. Carpenter, J. E.; Weinhold, F. Analysis of the Geometry of the Hydroxymethyl Radical by the "Different Hybrids for Different Spins" Natural Bond Orbital Procedure. J. Mol. Struct. (Theochem) 1988, 46, 41-62.
55. Reed, A. E.; Weinstock, R. B.; Weinhold, F. Natural Population Analysis. J. Chem. Phys. 1985, 83, 735-746.
56. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint. Chem. Rev. 1988, 88, 899-926.
57. Helgaker, T., Watson, M., Handy, N. C. Analytical Calculation of Nuclear Magnetic Resonance Indirect Spin-Spin Coupling Constants at the Generalized Gradient Approximation and Hybrid Levels of Density-Functional Theory. J. Chem. Phys. 2000, 113, 9402-9409.
58. Kutzelnigg, W.; Fleischer, U.; Schindler, M. in NMR-Basic Principles and Progress; Springer: Heidelberg, 1990, 23, 165.
59. COLOGNE2000, Kraka, E.; Gräfenstein, J.; Gauss, J.; He, Y.; Reichel, F.; Olsson, L.; Konkoli, Z.; He, Z.; Cremer, D. Göteborg University, Göteborg, 2000.
60. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.5, Gaussian, Inc., Pittsburgh PA, 1998.
61. Fantoni, R.; van Hlevoort, K.; Knippers, W.; Reuss, J. Direct Observation of Torsional Levels in Raman Spectra of Ethane. Chem. Phys. 1986, 110, 1-16.
62. 2. J. Chem. Phys., 1979, 71, 1183-1187.
63. Munoz-Caro, C.; Nino, A.; Senent, M. L. Theoretical Study of the Effect of Torsional Anharmonicity on the Thermodynamic Properties of Methanol. Chem. Phys. Lett., 1997, 273, 135-140.
64. For a recent review, see Goodman, L.; Pophristic, V. In Encyclopedia of Computational Chemistry, Schleyer, P. v. R.; Allinger, N. L.; Clark, T.; Gasteiger, J.; Kollman, P. A.; Schaefer III, H. F.; Schreiner, P. R. Eds. John Wiley:Chichester, UK, 1998, Vol. 4, p. 2525.
65. Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer Verlag: New York, 1983.
66. 17O NMR Spectroscopy in Organic Chemistry, CRC Press, Boca Raton, 1991.
67. Perlin, A. S.; Casu, B. Carbon-13 and Proton Magnetic Resonance Spectra of D-glucose-13C. Tetrahedron Lett. 1969, 2921-2924.
68. Podlasek, C. A.; Stripe, W. A.; Carmichael, I.; Shang, M.; Basu, B.; Serianmi, A. S. 13C-1H Spin-Coupling Constants in the β-D-Ribofuranosyl Ring: Effect of Ring Conformation on Coupling Magnitudes. J. Am. Chem. Soc. 1996, 118, 1413-1425.
69. Cavasotto, C. N.; Giribet, C. G.; Ruiz De Azua, M. C.; Contreras, R. H. Exo-Exo and Endo-Endo Vicinal Proton Spin-Spin Coupling Constants in Norbornane and Norbornene. An IPPP-CLOPPA Analysis. J. Comput. Chem 1991, 12, 141-146.
70. Barfield, M. in Encyclopedia of Nuclear Magnetic Resonance, Grant, D. M.; Harris, R. K., Edt.s, Wiley: Chichester, UK, 1996, p. 2520.
71. Marshall, J.; Walter, S. R.; Barfield, M.; Marchand, A. P.; Marchand, N. W.; Segre, A. L. Reasons for the Nonequivalence of the Exo-Exo and Endo-Endo Vicinal NMR Coupling Constants in Norbornanes. Tetrahedron 1976, 32, 537-542.