Temperature- and pressure-induced proton transfer in the 1:1 adduct formed between squaric acid and 4,4-bipyridine

Journal of the American Chemical Society

Volumn 131, Issue 11, 2009, Pages 3884-3893

  Martins, David M S ^a   Middlemiss, Derek S ^b   Pulham, Colin R ^a   Wilson, Chick C ^b   Weller, Mark T ^c   Henry, Paul F ^d   Shankland, Norman ^e   Shankland, Kenneth ^f   Marshall, William G ^f   Ibberson, Richard M ^f   Knight, Kevin ^f   Moggach, Stephen ^a   Brunelli, Michela ^g   Morrison, Carole A ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b UNIVERSITY OF GLASGOW   (United Kingdom)

^c UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^d INSTITUT LAUE LANGEVIN   (France)

^e UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^f RUTHERFORD APPLETON LABORATORY   (United Kingdom)

^g EUROPEAN SYNCHROTRON RADIATION FACILITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; DIAMOND FILMS; DIFFRACTION; ORGANIC POLYMERS; PHASE TRANSITIONS; POWDERS;

BIPYRIDINE; CHARGE STATE; CHARGE TRANSFER ENERGY; COLOR CHANGES; COMPUTATIONAL MODELING; DIFFRACTION METHODS; GASPHASE; HIGH FLUX; HIGH PRESSURE; HIGH TEMPERATURE; MOLECULAR IONS; ORIGINAL STRUCTURES; POWDER X RAY DIFFRACTION; SQUARIC ACIDS;

PROTON TRANSFER;

4,4' BIPYRIDINE; SQUARIC ACID; 4,4'-BIPYRIDYL; CYCLOBUTANE DERIVATIVE; PROTON; PYRIDINE DERIVATIVE;

ARTICLE; COMPUTER MODEL; CRYSTAL STRUCTURE; GAS; INFRARED SPECTROSCOPY; NEUTRON DIFFRACTION; PHASE TRANSITION; PHYSICAL PHASE; PRESSURE; PROTON TRANSPORT; SOLID; TEMPERATURE; X RAY POWDER DIFFRACTION; CHEMISTRY;

CYCLOBUTANES; PRESSURE; PROTONS; PYRIDINES; TEMPERATURE;

EID: 67749088360     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8082973     Document Type: Article

References (51)

1. Williams, R. J. P. Annu. Rev. Biophys., Biophys. Chem. 1988,17,71.
2. Kreuer, K. D. Chem. Mater. 1996, 8, 610.
3. Scherl, M.; Haarer, D.; Fischer, J.; DeCian, A.; Lehn, J.-M.; Eichen, Y. J. Phys. Chem. 1996, 100, 16175.
4. Kummer, L.; Wohrl, H.; Haarer, D. Chem. Phys. Lett. 1994, 227, 337.
5. Gilli, P.; Bertolasi, V.; Pretto, L.; Lycka, A.; Gilli, G. J. Am. Chem. Soc. 2002, 124, 13554.
6. Desiraju, G. R.; Boese, R.; Jetti, R. K. R.; Thakur, T. S.; Vangala, V. R. Chem. Commun. 2004, 2526.
7. Brougham, D. F.; Horsewill, A. J.; Ikram, A.; Ibberson, R. M.; McDonald, P. J.; Pinter-Krainer, M. J. Chem. Phys. 1996, 105, 979.
8. Middlemiss, D. S.; Facchini, M.; Morrison, C. A.; Wilson, C. C. CrysEngComm 2007, 9, 777.
9. Wilson, C. C.; Goeta, A. E. Angew. Chem, Int. Ed. 2004, 43, 2095.
10. Song, X.-J.; McDermott, A. E. Magn. Reson. Chem. 2001, 39,37.
11. Peng, B.-H.; Liu, G.-F.; Liu, L.; Jia, D.-Z. Tetrahedron 2005, 61, 5926.
12. Chierotti, M. R.; Gobetto, R. Chem. Commun. 2008, 14, 1621.
13. Wilson, C. C.; Shankland, N.; Florence, A. J. Chem. Phys. Lett. 1996, 253, 103.
14. Wilson, C. C.; Xu, X.; Florence, A. J.; Shankland, N.; New, J. Chem. 2006, 30, 979.
15. Reetz, M. T.; Hoger, S.; Harms, K. Aneew. Chem, Int. Ed. Enel. 1994. 33, 181.
16. Bernstein, J. Polymorphism in Molecular Crystals, IUCr monographs on Crystallography; Clarendon Press: Oxford, 2002.
17. Browne, W. R.; O'Connor, C. M.; Killeen, J. S.; Guckian, A. L.; Burke, M.; James, P.; Burke, M.; Vos, J. G. Inorg. Chem. 2002, 41, 4245.
18. SAINT Area-Detector Software Package v7.01A; Bruker AXS: Madison, WI, 2003.
19. Sheldrick, G. M. SADABS v2.04; University of Gottigen: Gottingen, Germany, 2001.
20. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Crystallogr. 1993, 26, 343.
21. Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W.; Cooper, R. I. CRYSTALS v12; Chemical Crystallography Laboratory: Oxford, UK, 2003.
22. Ibberson, R. M.; David, W. I. F., Knight, K. S. Report RAL-92-031; Rutherford Appleton Laboratory: Chilton, UK, 1992.
23. Hansen, T. C.; Henry, P. F.; Fischer, H. E.; Torregrossa, J.; Convert, P. Meas. Sci. Technol. 2008, 19, 034001.
24. Maslen, E. N. Int. Tables Crystallogr. 2006, 6, 600.
25. Rietveld, H. M. Acta Crystallogr. 1967, 22, 151.
26. Larson, A. C.; Von Dreele, R. B. GSAS, Report LAUR86-748; Los Alamos National Laboratory: Los Alamos, NM, 2004.
27. Toby, B. H. J. Appl. Crystallogr. 2001, 34, 210.
28. Pawley, G. S. J. Appl. Crystallogr. 1981, 14, 357.
29. Coelho, A. A. TOPAS; Bruker AXS: Karlsruhe, Germany, 2003.
30. David, W. I. F.; Shankland, K.; van de Streek, J.; Pidcock, E.; Motherwell, W. D. S.; Cole, J. C. J. Appl. Crystallogr. 2006, 39, 910.
31. CPMD version 3.11.1, Copyright IBM Corp. 1990-2006, Copyright MPI fur estkorperforschung Stuttgart, 1997-2001.
32. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1997, 78, 1396.
33. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865.
34. Vanderbilt, D. Phys. Rev.B 1990, 41, 7892.
35. Nose, S. J. Chem. Phys. 1984, 81, 511.
36. Hoover, W. G. Phys. Rev.A 1985, 31, 1695.
37. Dovesi, R.; Saunders, V. R.; Roetti, C.; Orlando, R.; Zicovich-Wilson, C. M.; Pascale, F.; Civalleri, B.; Doll, K.; Harrison, N. M.; Bush, I. J.; D'Arco, P.; Llunell, M. CRYSTAL06; University of Torino: Torino, Italy, 2006.
38. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
39. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639.
40. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
41. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev.B 1988, 37, 785.
42. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
43. Muscat, J.; Wander, A.; Harrison, N. M. Chem. Phys. Lett. 2001, 342, 397.
44. Perger, W. F. Chem. Phys. Lett. 2002, 368, 319.
45. Monkhorst, H. J.; Pack, J. D. Phys. Rev.B1976, 13, 5188.
46. Frisch, M. J.; Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
47. Leech, C. J.; Fabbiani, F. P. A.; Shankland, K.; David, W. I. F.; Ibberson, R. M. Acta Crystallogr. B 2008, 64, 101.
48. Flyvbjerg, H.; Petersen, H. G. J. Chem. Phys. 1989, 91, 461.
49. Chisholm, J. A.; Motherwell, S.; Tulip, P. R.; Parsons, S.; Clark, S. J. Cryst. Growth Des. 2005, 5, 1437.
50. Wiberg, K. B.; Rablen, P. R. J. Comput. Chem. 1993, 14, 1504.
51. Allen, M. P.; Tildesley, D. J., Computer Simulation of Liquids; Clarendon Press: Oxford, 1989.