1H NMR spectra. Part 30: 1H chemical shifts in amides and the magnetic anisotropy, electric field and steric effects of the amide group

Magnetic Resonance in Chemistry

Volumn 51, Issue 3, 2013, Pages 143-155

  Abraham, Raymond J ^a   Griffiths, Lee ^b   Perez, Manuel ^c  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c MESTRELAB RESEARCH   (Spain)

Author keywords

amides; conformational analysis; DFT and semi empirical calculations

Indexed keywords

AMIDES; AROMATIC COMPOUNDS; AROMATIZATION; ATOMS; CONFORMATIONS; DENSITY FUNCTIONAL THEORY; ELECTRIC FIELDS; MAGNETIC ANISOTROPY; MAGNETIC FIELD EFFECTS; MEAN SQUARE ERROR; MOLECULAR ORBITALS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALIPHATIC AMIDES; AMIDE GROUPS; AROMATIC AMIDES; ATOMIC ORBITAL; CONFORMATIONAL ANALYSIS; DFT AND SEMI-EMPIRICAL CALCULATIONS; FIELD-EFFECT; H NMR SPECTRA; SEMI-EMPIRICAL APPROACH; STERIC EFFECT;

CHEMICAL SHIFT;

AMIDE; PROTON;

ANISOTROPY; CHEMICAL STRUCTURE; CHEMISTRY; MAGNETIC FIELD; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STANDARD; STANDARDS; STEREOISOMERISM; ARTICLE;

AMIDES; ANISOTROPY; MAGNETIC FIELDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PROTONS; REFERENCE STANDARDS; STEREOISOMERISM;

EID: 84873702979     PISSN: 07491581     EISSN: 1097458X     Source Type: Journal    
DOI: 10.1002/mrc.3920     Document Type: Article

References (58)

1. R. J. Abraham, P. Leonard,. Magn. Reson. Chem. 2012, 51, 9.
2. H. S. Gutowsky,. J. Chem. Phys. 1956, 25, 1228.
3. L. Pauling, Nature of the Chemical Bond, 3rd edn, Cornell Univ. Press, Ithaca, NY, 1960.
4. W. E. Stewart, T. H. Siddall III,. Chem. Rev. 1970, 70, 517.
5. W. D. Phillips,. J. Chem. Phys. 1955, 23, 1363.
6. L. A. LaPlanche, M. T. Rogers,. J. Am. Chem. Soc. 1964, 86, 337.
7. M. Kitano, T. Fukuyama, K. Kuchitsu,. Bull. Chem. Soc. Jpn. 1973, 46, 384.
8. E. L. Hansen, N. W. Larsen, M. Nicolaisen,. Chem. Phys. Lett. 1980, 69, 327.
9. G. A. Jeffrey, J. R. Ruble, R. K. McMullan, D. J. DeFrees, J. A. Pople,. Acta Cryst., Sect. B 1980, 36, 2292.
10. K. T. Lim, M. M. Francl,. J. Chem. Phys. 1987, 91, 2716.
11. P. G. Jasien, W. J. Stevens, M. J. Krauss,. Mol. Struct. 1986, 139, 197.
12. M. W. Wong, K. B. Wiberg,. J. Phys. Chem. 1992, 96, 668.
13. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian03 Revision E.01, Gaussian, Wallingford CT, 2004.
14. M. Ramek, C. H. Yu, J. Sakon, L. Schäfer,. J. Phys. Chem. A 2000, 104, 9636.
15. M. P. Williamson, T. Asakura, E. Nakamura, M. Demura,. J. Biomol. NMR 1992, 2, 83.
16. M. P. Williamson, T. Asakura,. J. Mag. Res, Series B 1993, 101, 63.
17. K. Ösapay, D. A. Case,. J. Am. Chem. Soc. 1991, 113, 9436.
18. R. J. Abraham, B. Bardsley, M. Mobli, R. J. Smith,. Magn. Reson. Chem. 2005, 43, 3.
19. 1H NMR Spectra of Organic Compounds, J. Wiley & Sons, Chichester, UK, 2008.
20. R. J. Abraham, P. Leonard, C. F. Tormena,. Magn. Reson. Chem. 2012, 50, 305.
21. R. J. Abraham, J. J. Byrne, L. Griffiths, M. Perez,. Magn. Reson. Chem. 2006, 44, 491.
22. NMRpredict, Modgraph Ltd., 1 Oakland view, Welwyn, Herts AL6 0RJ, UK.
23. R. J. Abraham, J. J. Byrne, M. Mobli, HSPEC, University of Liverpool, 2006.
24. S. M. Castellano, A. A. Bothner-By,. J. Chem. Phys. 1967, 47, 5443.
25. H. M. McConnell,. J. Chem. Phys. 1957, 27, 226.
26. R. J. Abraham, M. Mobli, R. J. Smith,. J. Chem. Soc. Perkin Trans 2 2002, 41, 26.
27. R. F. Zürcher,. Prog. in Nuc. Magn. Reson. Spect. 1967, 2, 205.
28. M. Perez, Ph.D. thesis, University of Liverpool, 2001.
29. st edn, Aldrich Chemical Company Inc., Milwaukee, Wisconsin, USA, 1993.
30. Bruker XWINNMR, Version 3.0, Bruker Corp, Stilbersteifen, Germany, 2001.
31. PCMODEL version 9.2, Serena Software. Box 3076, Bloomington, Indiana,USA, 2007.
32. P. Pulay, J. F. Hinton, Encyclopedia of Nuclear Magnetic Resonance, New York, 1995.
33. E. Hirota, R. Sugisaki, R. Nielsen, J. Sorensen,. J. Mol. Spectrosc. 1974, 49, 251.
34. M. Kitano, K. Kuchitsu,. Bull. Chem. Soc. Jpn. 1974, 47, 61.
35. C. C. Costain, J. H. Dowling,. J. Chem. Phys. 1973, 46, 3048.
36. E. D. Stevens,. Acta Crystallogr., Sect. B 1978, 34, 544.
37. F. K. Winkler, J. D. Dunitz,. Acta Crystallogr., Sect. B 1975, 31, 281.
38. M. Barfield, A. S. Babaqi,. Magn. Reson. Chem. 1987, 25, 443.
39. P. Piaggio, Tesi di Laurea, University of Genova, 1996.
40. G. Müller, M. Lutz, S. Harder,. Acta Crystallogr., Sect. B 1996, 52, 1014.
41. A. J. R. Bourn, D. G. Gillies, E. W. Randall,. Tetrahedron 1966, 22, 1825.
42. C. C. F. Blake, R. W. H. Small,. Acta Cryst. B 1972, 28, 2201.
43. R. K. Pierens,. J. Chem. Soc. Perkin Trans 1980, 2, 235.
44. I. A. Rae, J. A. Weingold, R. H. Contreras, R. R. Bickofsky,. Magn. Reson. Chem. 1993, 31, 836.
45. C. Scholz, G. Scherer, L. Mayr, T. Schindler, F. X. Schmid,. Biol. Chem. 1998, 379, 361.
46. B. Sunners, L. H. Piette, W. G. Schneider,. Can. J. Chem. 1960, 38, 681.
47. A. J. R. Bourn, D. G. Gillies, E. W. Randall,. Tetrahedron 1964, 20, 1811.
48. R. E. Carter,. Acta Chem. Scand. 1967, 21, 75.
49. AIST:RIO-DB01 Spectral Data Base for Organic Compounds, SDBS. 2010.
50. S. Combrisson, B. P. Roques,. Tetrahedron 1976, 32, 1507.
51. K. Umemoto, K. Ouchi,. Org. Mag. Res. 1981, 15, 13.
52. I. Ledneczki, P. Forgo, J. T. Kiss, A. Molnair, L. Palinko,. J.Mol.Struct 2007, 834, 349.
53. J. M. Purcell, H. Susi, J. R. Cavanaugh,. Canad J. Chem 1969, 47, 3655.
54. S. S. Kuo, Computer Applications of Numerical Methods, Addison-Wesley Publishing Company, London, Chap. 8, 1972.
55. R. J. Abraham, N. J. Ainger, J. Chem. Soc. Perkin Trans2 1998, 441.
56. R. J. Abraham, Unpublished Results.
57. J. W. ApSimon, P. V. DeMarco, D. W. Mathieson,. Tetrahedron 1970, 26, 119.
58. H. J. Schneider, U. Buchheit, N. Becker, G. Schimdt, U. Siehl,. J. Am. Chem. Soc. 1985, 107, 7027.