H1 NMR spectra part 31: 1H chemical shifts of amides in DMSO solvent

Magnetic Resonance in Chemistry

Volumn 52, Issue 7, 2014, Pages 395-408

  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; NMR; solvent effects; density

Indexed keywords

CHEMICAL SHIFT; ELECTRIC FIELD EFFECTS; HYDROGEN BONDS; MAGNETIC ANISOTROPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLVENTS;

AMIDE GROUPS; ANISOTROPY EFFECT; BENZAMIDES; CLOSE RANGE; FUNCTIONAL APPROACH; NMR SPECTRUM; SOLVENT EFFECTS; SOLVENT SHIFT; STERIC EFFECT; Π DENSITY;

AMIDES;

AMIDE; DIMETHYL SULFOXIDE; PROTON; SOLVENT;

CHEMICAL MODEL; CHEMISTRY; COMPARATIVE STUDY; COMPUTER SIMULATION; PROCEDURES; PROTON NUCLEAR MAGNETIC RESONANCE;

AMIDES; COMPUTER SIMULATION; DIMETHYL SULFOXIDE; MODELS, CHEMICAL; PROTON MAGNETIC RESONANCE SPECTROSCOPY; PROTONS; SOLVENTS;

EID: 84902086621     PISSN: 07491581     EISSN: 1097458X     Source Type: Journal    
DOI: 10.1002/mrc.4079     Document Type: Article

References (51)

1. R. J. Abraham, L. Griffiths, M. Perez,. Magn. Reson. Chem. 2013, 51, 143.
2. a) A. D. Buckingham, T. Schaefer, W. G. Schneider,. J. Chem. Phys. 1960, 32, 1227
3. b) A. D. Buckingham,. Can. J. Chem. 1960, 68, 301.
4. R. J. Abraham,. Mol. Phys. 1961, 4, 369, J.Chem.Phys. 1961, 34, 1062.
5. W. T. Raynes, A. D. Buckingham, H. J. Bernstein,. J. Chem. Phys. 1962, 36, 3481.
6. L. Onsager,. J. Am. Chem. Soc. 1936, 58, 1486.
7. a) J. Homer,. Chem. Soc. Specialist Period. Rev. 1978, 7, 318
8. b) C. Jameson, ibid, 1980, 9, 61
9. c) P. Laszlo,. Prog. Nucl. Magn. Reson. Spectrosc. 1967, 3, 232.
10. M. W. Wong, M. J. Frisch, K. B. Wiberg,. J. Am. Chem. Soc. 1991, 113, 4776.
11. R. J. Abraham, M. A. Cooper,. J. Chem. Soc. 1967, 202.
12. R. J. Abraham, E. Bretschneider, Internal Rotation of Molecules, (Ed., W. J. Orville-Thomas,), A. Press, London, 1974, pp. 481-584, Ch 13.
13. C. J. Cramer, D. G. Truhlar,. Chem. Rev. 1999, 99, 2161.
14. T. Helgaker, M. Jaszunski, K. Ruud,. Chem. Rev. 1999, 99, 293.
15. J. Tomasi, M. Persico,. Chem. Rev. 1994, 94, 2027.
16. R. Cammi, B. Mennuci, J. Tomasi,. J. Chem. Phys. 1999, 110, 7627.
17. J. Tomasi, B. Mennucci, R. Cammi,. Chem. Rev. 2005, 105, 2999.
18. 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, Helgaker, Gaussian, Wallingford CT, 2004.
19. J. S. Lomas,. Magn. Reson. Chem. 2013, 51, 32.
20. W. E. Stewart, T. H. Siddall III,. Chem. Rev. 1970, 70, 517.
21. M. åOki, Applications of Dynamic NMR Spectroscopy to Organic Chemistry, VCH Publishers, Deerfield Beach, FL, 1985.
22. 1H NMR Spectra of Organic Compounds, J. Wiley & Sons, Chichester, UK, 2008.
23. a) R. J. Abraham, P. Leonard, C. F. Tormena,. Magn. Reson. Chem. 2012, 50, 305
24. b) R. J. Abraham, M. Mobli, ibid, 2007, 45, 865
25. c) E. A. Basso, G. F. Gauze, R. J. Abraham, ibid, 2007, 45, 749.
26. R. J. Abraham, J. J. Byrne, L. Griffiths, M. Perez,. Magn. Reson. Chem. 2006, 44, 491.
27. NMRpredict, Modgraph Ltd., 1 Oakland view, Welwyn, Herts AL6 0RJ, UK.
28. HSPEC, R. J. Abraham, J. J. Byrne, M. Mobli, University of Liverpool, 2006.
29. S. M. Castellano, A. A. Bothner-By,. J. Chem. Phys. 1967, 47, 5443.
30. a) K. Yamauchi, S. Kuroki, K. Fulii, I. Ando,. Chem. Phys. Lett. 2000, 324, 435
31. b) L. Yao, A. Grishaev, G. Cornilescu, A. Bax,. J. Amer. Chem. Soc. 2010, 132, 10866.
32. S. S. Kuo, Computer Applications of Numerical Methods, Addison-Wesley Publishing Company, London, Chap. 8, 1972.
33. 1H FT-NMR Spectra (1st edn), Aldrich Chemical Company Inc., Milwaukee, Wisconsin, USA,1993.
34. R. Rittner, Private Communication.
35. M. Perez, Ph.D. Thesis, University of Liverpool, 2001.
36. Bruker X. W. I. N. N. M. R., Version 3.0, Bruker Corp., Stilbersteifen, Germany, 2001.
37. PCMODEL, Version 9.2, Serena Software. Box 3076, Bloomington, Indiana,USA 2007.
38. P. Pulay, J. F. Hinton, Encyclopedia of Nuclear Magnetic Resonance, J. Wiley & Sons, New York, 1995.
39. B. Sunners, L. H. Piette, W. G. Schneider,. Can. J. Chem. 1960, 38, 681.
40. M. J. Deetz, J. E. Fahey, B. D. Smith,. J. Phys. Org. Chem. 2001, 14, 463.
41. Astra-Zeneca Alderly Park, Macclesfield, Cheshire SK10 4TG.
42. T. Mizuno, J. Takahashi, A. Ogawa,. Tetrahedron 2002, 58, 7805.
43. K. Tonan, K. Adachi, S. Ikawa,. Spec. Acta part A 1998, 54, 989.
44. P. W. von Ostwalden, J. D. Roberts,. J. Org. Chem. 1971, 36, 3792.
45. a) R. H. Cox, A. A. Bothner-By,. J. Phys. Chem. 1969, 73, 2465
46. b) R. A. Coburn, G. O. Dudek,. J. Phys. Chem. 1968, 72, 1177.
47. J. Frank, A. R. Katritzky,. J. Chem. Soc. Perkin Trans. 2 1976, 1428.
48. A. J. R. Bourn, D. G. Gillies, E. W. Randall,. Tetrahedron 1966, 22, 1825.
49. AIST:RIO-DB01 Spectral Data Base for Organic Compounds, SDBS. 2010
50. D. J. Calvert, C. J. O'Connor,. Aus. J. Chem. 1979, 32, 337.
51. M. P. Williamson, T. Asakura,. J. Mag. Res, Series B 1993, 101, 63.