Proton transfer and hydrogen bonding in the organic solid state: A combined XRD/XPS/ssNMR study of 17 organic acid-base complexes

Physical Chemistry Chemical Physics

Volumn 16, Issue 3, 2014, Pages 1150-1160

  Stevens, Joanna S ^a   Byard, Stephen J ^b   Seaton, Colin C ^a   Sadiq, Ghazala ^a   Davey, Roger J ^a   Schroeder, Sven L M ^a,c  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b Sanofi Aventis Isotope Chemistry and Metabolite Synthesis Northumberland   (United Kingdom)

^c UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENESULFONIC ACID DERIVATIVE; BENZOIC ACID DERIVATIVE; CITRIC ACID; FUMARIC ACID; FUMARIC ACID DERIVATIVE; GLUTARIC ACID; GLUTARIC ACID DERIVATIVE; HYDROCHLORIC ACID; MALONIC ACID; MALONIC ACID DERIVATIVE; OXALIC ACID; PROTON; SALICYLIC ACID DERIVATIVE; SULFOSALICYLIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; QUANTUM THEORY; SPECTROPHOTOMETRY; X RAY; X RAY CRYSTALLOGRAPHY;

BENZENESULFONATES; BENZOATES; CITRIC ACID; CRYSTALLOGRAPHY, X-RAY; FUMARATES; GLUTARATES; HYDROCHLORIC ACID; HYDROGEN BONDING; MALONATES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXALIC ACID; PROTONS; QUANTUM THEORY; SALICYLATES; SPECTROPHOTOMETRY; X-RAYS;

EID: 84890283041     PISSN: 14639076     EISSN: None     Source Type: Journal    
DOI: 10.1039/c3cp53907e     Document Type: Article

References (64)

1. N. Schultheiss A. Newman Cryst. Growth Des. 2009 95 499 516
2. P. Vishweshwar J. A. McMahon J. A. Bis M. J. Zaworotko J. Pharm. Sci. 2006 95 499 516
3. C. B. Aakeroy M. E. Fasulo J. Desper Mol. Pharmaceutics 2007 4 317 322
4. Handbook of Pharmaceutical Salts: Properties, Selection, and Use, Wiley-VCH, Weinheim, 2002
5. Z. J. Li Y. Abramov J. Bordner J. Leonard A. Medek A. V. Trask J. Am. Chem. Soc. 2006 128 8199 8210
6. D. P. McNamara S. L. Childs J. Giordano A. Iarriccio J. Cassidy M. S. Shet R. Mannion E. O'Donnell A. Park Pharm. Res. 2006 23 1888 1897
7. A. V. Trask W. D. S. Motherwell W. Jones Int. J. Pharm. 2006 320 114 123
8. C. C. Sun H. Hou Cryst. Growth Des. 2008 8 1575 1579
9. M. Viertelhaus R. Hilfiker F. Blatter M. Neuburger Cryst. Growth Des. 2009 9 2220 2228
10. S. Chattoraj L. Shi C. C. Sun CrystEngComm 2010 12 2466 2472
11. C. M. Reddy G. R. Krishna S. Ghosh CrystEngComm 2010 12 2296 2314
12. S. L. Childs G. P. Stahly A. Park Mol. Pharmaceutics 2007 4 323 338
13. C. B. Aakeroy A. Rajbanshi Z. J. Li J. Desper CrystEngComm 2010 12 4231 4239
14. M. Byres P. J. Cox G. Kay E. Nixon CrystEngComm 2009 11 135 142
15. D. M. S. Martins D. S. Middlemiss C. R. Pulham C. C. Wilson M. T. Weller P. F. Henry N. Shankland K. Shankland W. G. Marshall R. M. Ibberson K. Knight S. Moggach M. Brunelli C. A. Morrison J. Am. Chem. Soc. 2009 131 3884 3893
16. S. Mohamed D. A. Tocher M. Vickers P. G. Karamertzanis S. L. Price Cryst. Growth Des. 2009 9 2881 2889
17. A. Parkin S. M. Harte A. E. Goeta C. C. Wilson New J. Chem. 2004 28 718 721
18. C. Wilson Crystallogr. Rev. 2007 13 143 198
19. R. Taylor O. Kennard Acta Crystallogr., Sect. B: Struct. Sci. 1983 39 133 138
20. A. V. Trask and W. Jones, in Organic Solid State Reactions, ed., F. Toda, Springer-Verlag, New York, 2005, pp. 41-70
21. J. S. Stevens S. J. Byard S. L. M. Schroeder Cryst. Growth Des. 2010 10 1435 1442
22. C. C. Wilson K. Shankland N. Shankland Z. Kristallogr. 2001 216 303 306
23. C. Wilson Acta Crystallogr., Sect. B: Struct. Sci. 2001 57 435 439
24. J. A. Cowan J. A. K. Howard G. J. McIntyre S. M. F. Lo I. D. Williams Acta Crystallogr., Sect. B: Struct. Sci. 2003 59 794 801
25. T. Steiner I. Majerz C. C. Wilson Angew. Chem., Int. Ed. 2001 40 2651 2654
26. C. C. Wilson N. Shankland A. J. Florence Chem. Phys. Lett. 1996 253 103 107
27. C. C. Wilson N. Shankland A. J. Florence J. Chem. Soc., Faraday Trans. 1996 92 5051 5057
28. J. S. Stevens S. J. Byard C. A. Muryn S. L. M. Schroeder J. Phys. Chem. B 2010 114 13961 13969
29. R. Gobetto C. Nervi E. Valfre M. R. Chierotti D. Braga L. Maini F. Grepioni R. K. Harris P. Y. Ghi Chem. Mater. 2005 17 1457 1466
30. J. S. Stevens S. J. Byard S. L. M. Schroeder J. Pharm. Sci. 2010 99 4453 4457
31. T. FriŠčić L. Fábián J. C. Burley D. G. Reid M. J. Duer W. Jones Chem. Commun. 2008 1644 1646
32. R. Gobetto C. Nervi M. R. Chierotti D. Braga L. Maini F. Grepioni R. K. Harris P. Hodgkinson Chem.-Eur. J. 2005 11 7461 7471
33. J. S. Stevens S. J. Byard C. C. Seaton G. Sadiq R. J. Davey S. L. M. Schroeder Angew. Chem., Int. Ed. 2011 50 9916 9918
34. P. A. Williams C. E. Hughes G. K. Lim B. M. Kariuki K. D. M. Harris Cryst. Growth Des. 2012 12 3104 3113
35. F. Bisti A. Stroppa S. Picozzi M. Donarelli S. Picozzi M. Coreno J. Chem. Phys. 2013 138 014308
36. J. S. Stevens S. L. M. Schroeder Surf. Interface Anal. 2009 41 453 462
37. G. Gilli and P. Gilli, The Nature of the Hydrogen Bond, Oxford University Press, Oxford, 2009
38. a DB 12.0), Advanced Chemistry Development, Inc. (ACD/Labs), Toronto, 2010
39. a values were obtained using ACD/PhysChem Suite v12.0, Advanced Chemistry Development, Inc. (ACD/Labs), Toronto, 2010
40. J. S. Stevens S. J. Byard C. C. Seaton G. Sadiq R. J. Davey S. L. M. Schroeder Angew. Chem. 2011 123 10090 10092
41. J. Madarász P. Bombicz K. Jármi M. Bán G. Pokol S. Gál J. Therm. Anal. Calorim. 2002 69 281 290
42. C. C. Seaton K. Chadwick G. Sadiq K. Guo R. J. Davey Cryst. Growth Des. 2009 10 726 733
43. K. Chadwick G. Sadiq R. J. Davey C. C. Seaton R. G. Pritchard A. Parkin Cryst. Growth Des. 2009 9 1278 1279
44. Avantium Crystal16® parallel crystallizer, Avantium, Amsterdam
45. G. M. Sheldrick Acta Crystallogr., Sect. A: Fundam. Crystallogr. 2008 64 112 122
46. A. Altomare G. Cascarano C. Giacovazzo A. Guagliardi M. C. Burla G. Polidori M. Camalli J. Appl. Crystallogr. 1994 27 435 436
47. N. Fairley and A. Carrick, The Casa Cookbook-Part 1: Recipes for XPS Data Processing, Acolyte Science, Knutsford, Cheshire, 2005
48. D. Briggs, M. P. Seah and P. M. A. Sherwood, in Practical Surface Analysis, Volume 1: Auger and X-ray Photoelectron Spectroscopy, ed., D. Briggs, and, M. P. Seah, John Wiley & Sons, Chichester, 2nd edn, 1990
49. D. Briggs G. Beamson Anal. Chem. 2002 64 1729 1736
50. The XPS of Polymers Database, Surface Spectra Ltd., Manchester, 2000
51. R. K. Harris E. D. Becker S. M. Cabral De Menezes R. Goodfellow P. Granger Pure Appl. Chem. 2001 73 1795 1818
52. R. K. Harris E. D. Becker S. M. Cabral De Menezes P. Granger R. E. Hoffman K. W. Zilm Pure Appl. Chem. 2008 80 59 84
53. J. R. Yates C. J. Pickard F. Mauri Phys. Rev. B: Condens. Matter Mater. Phys. 2007 76 024401
54. M. D. Segall P. L. D. Lindan M. J. Probert C. J. Pickard P. J. Hasnip S. J. Clark M. C. Payne J. Phys.: Condens. Matter 2002 14 2717 2743
55. S. J. Clark M. D. Segall C. J. Pickard P. J. Hasnip M. I. J. Probert K. Refson M. C. Payne Z. Kristallogr. 2005 220 567 570
56. R. K. Harris P. Hodgkinson C. J. Pickard J. R. Yates V. Zorin Magn. Reson. Chem. 2007 45 S174 S186
57. Materials Studio version 4.4, Accelrys, Inc., San Diego, 2010
58. J. S. Stevens S. J. Byard E. Zlotnikov S. L. M. Schroeder J. Pharm. Sci. 2010 100 942 948
59. C. G. Levy and R. L. Litcher, Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy, Wiley, New York, 1979
60. NMR Crsytallography, John Wiley & Sons Ltd, Chichester, 2009
61. P. Gilli L. Pretto G. Gilli J. Mol. Struct. 2007 844-845 328 339
62. P. Gilli L. Pretto V. Bertolasi G. Gilli Acc. Chem. Res. 2009 42 33 44
63. K. Siegbahn, ESCA: Atomic, Molecular, and Solid State Structure Studied by Means of Electron Spectroscopy, Almqvist & Wiksells, Uppsala, 1967
64. R. J. Davey S. L. M. Schroeder J. H. ter Horst Angew. Chem., Int. Ed. 2013 52 2166 2179