An NMR method for the quantitative assessment of intramolecular hydrogen bonding; Application to physicochemical, environmental, and biochemical properties

Journal of Organic Chemistry

Volumn 79, Issue 22, 2014, Pages 11075-11083

  Abraham, Michael H ^a   Abraham, Raymond J ^b   Acree, William E ^c   Aliev, Abil E ^a   Leo, Al J ^d   Whaley, William L ^e  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

^c UNIVERSITY OF NORTH TEXAS   (United States)

^d SeeByte Ltd   (United States)

^e TARLETON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL SHIFT; COMPLEXATION; DIMETHYL SULFOXIDE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS;

BIOCHEMICAL PROPERTIES; HYDROXY COMPOUNDS; INTRA-MOLECULAR HYDROGEN BONDS; INTRAMOLECULAR HYDROGEN BONDING; NH GROUPS; NMR CHEMICAL SHIFTS; OH GROUP; QUANTITATIVE ASSESSMENTS;

HYDROGEN BONDS;

DIMETHYL SULFOXIDE; HYDROXYL GROUP; SOLVENT;

ACIDITY; ANALYTIC METHOD; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CLINICAL ASSESSMENT; CONTROLLED STUDY; ENVIRONMENTAL IMPACT; HYDROGEN BOND; MATHEMATICAL ANALYSIS; NUCLEAR MAGNETIC RESONANCE; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; STRUCTURAL EQUATION MODELING;

EID: 84912571178     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502080p     Document Type: Article

References (39)

1. Shalaeva, M.; Caron, G.; Abramov, Y. A.; OConnell, T. N.; Plummer, M. S.; Yalamanchi, G.; Farley, K. A.; Goetz, G. H.; Philippe, L.; Shapiro, M. J. J. Med. Chem. 2013, 56, 4870-4879
2. El Tayar, N.; Tsai, R.-S.; Testa, B.; Carrupt, P.-A.; Leo, A. J. Pharm. Sci. 1991, 80, 590-598
3. El Tayar, N.; Testa, B.; Carrupt, P.-A. J. Phys. Chem. 1992, 96, 1456-1461
4. El Tayar, N.; Mark, A. E.; Vallat, P.; Brunne, R. M.; Testa, B.; van Gunsteren, W. F. J. Med. Chem. 1993, 36, 3757-3764
5. Steyaert, G.; Lisa, G.; Gaillard, P.; Boss, G.; Reymond, F.; Girault, H. H.; Carrupt, P.-A.; Testa, B. J. Chem. Soc., Faraday Trans. 1997, 93, 401-406
6. Leo, A. J. J. Pharm. Sci. 2000, 89, 1567-1578
7. Feng, L.; Han, S.; Wang, L. Chin. Sci. Bull. 1996, 41, 732-735
8. Abraham, M. H. Chem. Soc. Rev. 1993, 22, 73-83
9. Abraham, M. H.; Ibrahim, A.; Zissimos, A. M. J. Chromatogr., A 2004, 1037, 29-47
10. Abraham, M. H.; Smith, R. E.; Luchtefeld, R.; Boorem, A. J.; Luo, R.; Acree, W. E., Jr. J. Pharm. Sci. 2010, 99, 1500-1515
11. Clarke, E. D.; Mallon, L. J. The Determination of Abraham Descriptors and Their Application to Crop Protection Research. In Modern Methods in Crop Protection Research; Jeschke, P.; Kramer, W.; Schirmer, U.; Witschel, M., Eds.; Wiley-VCH: Weinheim, Germany, 2012; pp 273-279.
12. Abraham, M. H.; Acree, W. E., Jr. Eur. Chem. Bull. 2013, 2, 1027-1037
13. COSMOtherm-BP-TZVP-C21-0111, 2013.
14. SPARC: http://ibmlc2.chem.uga.edu/sparc/.
15. Goetz, G. H.; Farrell, W.; Shalaeva, M.; Sciabola, S.; Anderson, D.; Yan, J.; Philippe, L.; Shapiro, M. J. J. Med. Chem. 2014, 57, 2920-2929
16. Abraham, M. H.; Abraham, R. J.; Byrne, J.; Griffiths, L. J. Org. Chem. 2006, 71, 3389-3394
17. Whaley, W. L.; Okoso-amaa, E. M.; Womack, C. L.; Vladimirova, A.; Rogers, L. B.; Risher, M. J.; Abraham, M. H. Nat. Prod. Commun. 2013, 8, 85-98
18. Siskos, M. G.; Kontogianni, V. G.; Tsiafoulis, C. G.; Tzakos, A. G.; Gerothanassis, I. P. Org. Biomol. Chem. 2013, 11, 7400-7411
19. Abraham, R. J.; Griffiths, L.; Perez, M. Magn. Reson. Chem. 2013, 51, 143-155
20. Abraham, R. J.; Griffiths, L.; Perez, M. Magn. Reson. Chem. 2014, 52, 395-408
21. Abraham, R. J.; Byrne, J. J.; Griffiths, L.; Perez, M. Magn. Reson. Chem. 2006, 44, 491-509
22. Abraham, R. J.; Mobli, M. Magn. Reson. Chem. 2007, 45, 865-877
23. 1H FT-NMR Spectra, 1 st ed.; Aldrich Chemical Company, 1993.
24. AIST:RIO-DB01 Spectral Data Base for Organic Compounds, SDBS, 2010.
25. Biali, S. E.; Rappoport, Z. J. Am. Chem. Soc. 1984, 106, 5641-5653
26. Lessene, G.; Smith, B. J.; Gable, R. W.; Baeli, J. B. J. Org. Chem. 2009, 74, 6511-6525
27. PCModel, version 9.2; Serena Software: Bloomington, IN, 2007.
28. Absolv, version 5.0; Advanced Chemistry Development: Toronto, ON.
29. Mazák, K.; Noszál, B. Eur. J. Pharm. Sci. 2014, 62, 98-104
30. Livingston, D.; Davis, A. Modeling Chemical Structure-Log P. In Drug Design Strategies: Quantitative Approaches; Royal Society of Chemistry: London, 2012; Chapter 7, p 192.
31. Abraham, M. H. J. Pharm. Sci. 2014, 103, 956-1966
32. Abraham, M. H. J. Pharm. Sci. 2011, 100, 1690-1701
33. Zhang, K.; Chen, M.; Scriba, G. K. E.; Abraham, M. H.; Fahr, A.; Lui, X. J. Pharm. Sci. 2011, 100, 3105-3113
34. Zhang, K.; Chen, M.; Scriba, G. K. E.; Abraham, M. H.; Fahr, A.; Lui, X. J. Pharm. Sci. 2012, 101, 2034-2044
35. Bronner, G.; Goss, K.-U. Environ. Sci. Technol. 2011, 45, 1313-1319
36. Poole, S. K.; Poole, C. F. J. Chromatogr., A 1999, 845, 381-400
37. Sprunger, L.; Proctor, A.; Acree, W. E., Jr.; Abraham, M. H. J. Chromatogr., A 2007, 1175, 162-173
38. Endo, S.; Hale, S. E.; Goss, K.-U.; Arp, H. P. H. Environ. Sci. Technol. 2011, 45, 10124-10132
39. Abraham, M. H.; Andonian-Haftvan, J.; Whiting, G. S.; Leo, A.; Taft, R. W. J. Chem. Soc., Perkin Trans. 2 1994, 1777-1791