Evaluation of the H-bonding properties of CH···O interactions based upon NMR spectra

Journal of Molecular Structure: THEOCHEM

Volumn 500, Issue 1-3, 2000, Pages 441-452

  Scheiner, S ^a   Gu, Y ^a   Kar, T ^a  

^a SOUTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

Ab initio; Chemical shift tensor; CSGT; DFT; GIAO

Indexed keywords

CARBON; HYDROGEN; OXYGEN;

ANISOTROPY; ARTICLE; HYDROGEN BOND; MATHEMATICAL ANALYSIS; MATHEMATICAL COMPUTING; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0034599853     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(00)00375-4     Document Type: Article

References (91)

1. Scheiner S. Maksic Z.B., Orville-Thomas W.J. Pauling's Legacy - Modern Modelling of the Chemical Bond. 1977;Elsevier, Amsterdam. (p. 571).
2. Jeffrey G.A. An Introduction to Hydrogen Bonding. 1977;Oxford University Press, New York.
3. Scheiner S. Hydrogen Bonding. A Theoretical Perspective. 1997;Oxford University Press, New York.
4. Badger R.M., Bauer S.H. J. Chem. Phys. 5:1939;839.
5. Pimentel G.C., McClellan A.L. The Hydrogen Bond. 1960;Freeman, San Francisco, CA.
6. Libowitzky E. Monat. Chem. 130:1999;1047.
7. Hinton J.F., Wolinski K. Hadzi D. Theoretical Treatments of Hydrogen Bonding. 1997;Wiley, Chichester. (p. 75).
8. Berglund B., Vaughan R.W. J. Chem. Phys. 73:1980;2037.
9. Jeffrey G.A., Yeon Y. Acta Crystallogr. B. 42:1986;410.
10. Ando S., Ando I., Shoji A., Ozaki T. J. Am. Chem. Soc. 110:1988;3380.
11. Hibbert F., Emsley J. Adv. Phys. Org. Chem. 26:1990;255.
12. Gerald R., Bernhard T., Haeberlen U., Rendell J., Opella S. J. Am. Chem. Soc. 115:1993;777.
13. Wu C.H., Ramamoorthy A., Gierasch L.M., Opella S.J. J. Am. Chem. Soc. 117:1995;6148.
14. Ramamoorthy A., Wu C.H., Opella S.J. J. Am. Chem. Soc. 119:1997;10 479.
15. Koller H., Lobo R.F., Burkett S.L., Davis M.E. J. Phys. Chem. 99:1995;12 588.
16. Eckert H., Yesinowski J.P., Silver L.A., Stolper E.M. J. Phys. Chem. 92:1988;2055.
17. Kaliaperumal R., Sears R.E.J., Ni Q.W., Furst J.E. J. Chem. Phys. 91:1989;7387.
18. Konrat R., Tollinger M., Kontaxis G., Kräutler B. Monat. Chem. 130:1999;961.
19. Del Bene J.E., Perera S.A., Bartlett R.J. J. Phys. Chem. A. 103:1999;8121.
20. Wagner G., Pardi A., Wüthrich K. J. Am. Chem. Soc. 105:1983;5948.
21. Kuntz I.D., Kosen P.A., Craig E.C. J. Am. Chem. Soc. 113:1991;1406.
22. Zhou N.E., Zhu B.-Y., Sykes B.D., Hodges R.S. J. Am. Chem. Soc. 114:1992;4320.
23. Huggins C.M., Pimentel G.C., Shoolery J.N. J. Chem. Phys. 23:1955;1244.
24. Slasinski F.M., Tustin J.M., Sweeney F.J., Armstrong A.M., Ahmed Q.A., Lorand J.P. J. Org. Chem. 41:1976;2693.
25. Sammes M.P., Harlow R.L. J. Chem. Soc. Perkin Trans. II. 1976;1130.
26. Li C., Sammes M.P. J. Chem. Soc. Perkin Trans. I. 1983;1303.
27. Li C., Sammes M.P. J. Chem. Soc. Perkin Trans. I. 1983;2193.
28. Mizuno K., Ochi T., Shindo Y. J. Chem. Phys. 109:1998;9502.
29. Afonin A.V., Vashchenko A.V., Takagi T., Kimura A., Fujiwara H. Can. J. Chem. 77:1999;416.
30. Gu Z., Zambrano R., McDermott A. J. Am. Chem. Soc. 116:1994;6368.
31. Asakawa N., Kuroki S., Kurosu H., Ando I., Shoji A., Ozaki T. J. Am. Chem. Soc. 104:1992;3261.
32. de Dios A.C., Oldfield E. J. Am. Chem. Soc. 116:1994;11 485.
33. Bachovchin W.W. Biochemistry. 25:1986;7751.
34. Perrin C.L., Nielson J.B. J. Am. Chem. Soc. 119:1997;12 734.
35. Rohlfing C.M., Allen L.C., Ditchfield R. Chem. Phys. Lett. 86:1982;380.
36. Rohlfing C.M., Allen L.C., Ditchfield R. J. Chem. Phys. 79:1983;4958.
37. Glasstone S. Trans. Faraday Soc. 33:1937;200.
38. Dippy J.F.J. Chem. Rev. 25:1939;151.
39. Sutor D.J. Nature. 195:1962;68.
40. Taylor R., Kennard O. J. Am. Chem. Soc. 104:1982;5063.
41. Desiraju G.R. Acc. Chem. Res. 24:1991;290.
42. Gavezzotti A. J. Phys. Chem. 95:1991;8948.
43. Steiner T. J. Chem. Soc. Perkin Trans. II. 1995;1315.
44. Steiner T., Kanters J.A., Kroon J. Chem. Commun. 1996;1277.
45. Allen F.H., Lommerse J.P.M., Hoy V.J., Howard J.A.K., Desiraju G.R. Acta Crystallogr. B. 52:1996;734.
46. Brandl M., Lindauer K., Meyer M., Sühnel J. Theor. Chem. Acc. 101:1999;103.
47. Pinchas S. J. Phys. Chem. 67:1963;1862.
48. Chaney J.D., Goss C.R., Folting K., Santarsiero B.D., Hollingsworth M.D. J. Am. Chem. Soc. 118:1996;9432.
49. Hobza P., Spirko V., Havlas Z., Buchhold K., Reimann B., Barth H.-D., Brutschy B. Chem. Phys. Lett. 299:1999;180.
50. Turi L., Danenberg J.J. J. Phys. Chem. 97:1993;7899.
51. Turi L., Danenberg J.J. J. Phys. Chem. 99:1995;639.
52. Rovira M.C., Novoa J.J., Whangbo M.-H., Williams J.M. Chem. Phys. 200:1995;319.
53. Alkorta I., Maluendes S. J. Phys. Chem. 99:1995;6457.
54. Koch U., Popelier P.L.A. J. Phys. Chem. 99:1995;9747.
55. Novoa J.J., Mota F. Chem. Phys. Lett. 266:1997;23.
56. Ornstein R.L., Zheng Y. J. Biomol. Struct. Dyn. 14:1997;657.
57. Hobza P., Spirko V., Selzle H.L., Schlag E.W. J. Phys. Chem. A. 102:1998;2501.
58. Hobza P., Havlas Z. Chem. Phys. Lett. 303:1999;447.
59. Masella M., Flament J.-P. J. Chem. Phys. 110:1999;7245.
60. Cubero E., Orozco M., Luque F.J. Chem. Phys. Lett. 310:1999;445.
61. Gu Y., Kar T., Scheiner S. J. Am. Chem. Soc. 121:1999;9411.
62. Gu Y., Kar T., Scheiner S. J. Mol. Struct. 2000;. in press.
63. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T.A. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J.J.P. Stewart, M. Head-Gordon, G. Gonzalez, J.A. Pople, GAUSSIAN 94 Gaussian, Inc., Pittsburgh, PA, 1995.
64. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, GAUSSIAN 98, Revision A.6, Gaussian, Inc., Pittsburgh, PA, 1998.
65. Møller C., Plesset M.S. Phys. Rev. 46:1934;618.
66. Pople J.A., Seeger R., Krishnan R. Int. J. Quantum Chem., Quantum Chem. Symp. 11:1977;149.
67. Becke A.D. J. Chem. Phys. 98:1993;5648.
68. Lee C., Yang W., Parr R.G. Phys. Rev. B. 37:1988;785.
69. Cheeseman J.R., Frisch M.J., Trucks G.W., Keith T.A. J. Chem. Phys. 104:1996;5497.
70. Ditchfield R. Mol. Phys. 27:1974;789.
71. Wolinski K., Hilton J.F., Pulay P. J. Am. Chem. Soc. 112:1990;8251.
72. Alkorta I., Elguero J. New J. Chem. 1998;381.
73. Rablen P.R., Pearlman S.A., Finkbiner J. J. Phys. Chem. A. 103:1999;7357.
74. Czernek J., Sklenár V. J. Phys. Chem. A. 103:1999;4089.
75. Chesnut D.B., Phung C.G. Chem. Phys. 147:1990;91.
76. Nymand T.M., Åstrand P.-O., Mikkelsen K.V. J. Phys. Chem. B. 101:1997;4105.
77. Martin N.H., Allen N.W., Ingrassia S.T., Minga E.K., Brown J.D. Struct. Chem. 10:1999;375.
78. Baldridge K.K., Siegel J.S. J. Phys. Chem. A. 103:1999;4038.
79. Barich D.H., Nicholas J.B., Xu T., Haw J.F. J. Am. Chem. Soc. 120:1998;12 342.
80. Chesnut D.B. Lipkowitz K.B., Boyd D.B. Reviews in Computational Chemistry. 1997;VCH Publishers, New York. (vol. 8).
81. Forsyth D.A., Sebag A.B. J. Am. Chem. Soc. 119:1997;9483.
82. Helgaker T., Jaszunski M., Ruud K. Chem. Rev. 99:1999;293.
83. Alkorta I., Elguero J. Struct. Chem. 9:1998;187.
84. Bühl M., Thiel W., Fleischer U., Kutzelnigg W. J. Phys. Chem. 99:1995;4000.
85. Pecul M., Sadlej J. Chem. Phys. 234:1998;111.
86. Gu Z., Drueckhammer D.G., Kurz L., Liu K., Martin D.P., McDermott A. Biochemistry. 38:1999;8022.
87. Aicken A.M., Buckingham A.D., Tantirungrotechai Y. Mol. Phys. 97:1999;167.
88. Cornilescu G., Hu J.-S., Bax A. J. Am. Chem. Soc. 121:1999;2949.
89. Cornilescu G., Ramirez B.E., Frank M.K., Clore G.M., Gronenborn A.M., Bax A. J. Am. Chem. Soc. 121:1999;6275.
90. Dingley A.J., Grzesiak S. J. Am. Chem. Soc. 120:1998;8293.
91. Dingley A.J., Masse J.E., Peterson R.D., Barfield M., Feigon J., Grzesiek S. J. Am. Chem. Soc. 121:1999;6019.