Solid-state NMR and computational investigation of solvent molecule arrangement and dynamics in isostructural solvates of droperidol

Solid State Nuclear Magnetic Resonance

Volumn 65, Issue , 2015, Pages 12-20

  Běrziņš, Agris ^a,b   Hodgkinson, Paul ^b  

^a UNIVERSITY OF LATVIA   (Latvia)

^b DURHAM UNIVERSITY   (United Kingdom)

Author keywords

Ab initio calculations; Droperidol; Hydrates solvates; Isostructural solvates; Motional broadening; Solid state NMR; Solvent dynamics; Spin lattice relaxation

Indexed keywords

CALCULATIONS; DYNAMICS; HYDRATES; HYDRATION; LIGHT POLARIZATION; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPIN DYNAMICS; SPIN-LATTICE RELAXATION;

AB INITIO CALCULATIONS; DROPERIDOL; ISOSTRUCTURAL; MOTIONAL BROADENING; SOLID STATE NMR; SOLVENT DYNAMICS;

ORGANIC SOLVENTS;

DROPERIDOL; SOLVENT;

CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; DROPERIDOL; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SOLVENTS;

EID: 84924537519     PISSN: 09262040     EISSN: 15273326     Source Type: Journal    
DOI: 10.1016/j.ssnmr.2014.09.001     Document Type: Article

References (65)

1. C.P. Price, G.D. Glick, and A.J. Matzger Angew. Chem. Int. Ed. 45 2006 2062 2066
2. A.L. Bingham, D.S. Hughes, M.B. Hursthouse, R.W. Lancaster, S. Tavener, and T.L. Threlfall Chem. Commun. 2001 603 604
3. L. Yu, G.A. Stephenson, C.A. Mitchell, C.A. Bunnell, S.V. Snorek, J.J. Bowyer, T.B. Borchardt, J.G. Stowell, and S.R. Byrn J. Am. Chem. Soc. 122 2000 585 591
4. D.E. Braun, T. Gelbrich, V. Kahlenberg, R. Tessadri, J. Wieser, and U.J. Griesser J. Pharm. Sci. 98 2009 2010 2026
5. J.B. Nanubolu, B. Sridhar, V.S.P. Babu, B. Jagadeesh, and K. Ravikumar CrystEngComm 14 2012 4677 4685
6. U.J. Griesser R. Hilfiker, Polymorphism in the Pharmaceutical Industry 2006 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim 211 233
7. T. Hosokawa, S. Datta, A.R. Sheth, N.R. Brooks, V.G. Young Jr, and D.J.W. Grant Cryst. Growth Des. 4 2004 1195 1201
8. R. Banerjee, P.M. Bhatt, and G.R. Desiraju Cryst. Growth Des. 6 2006 1468 1478
9. N. Stieger, W. Liebenberg, J. Wessels, H. Samsodien, and M. Caira Struct. Chem. 21 2010 771 777
10. N. Schultheiss, J.P. Smit, and J.A. Hanko Eur. J. Pharm. Sci. 38 2009 498 503
11. D.E. Braun, T. Gelbrich, V. Kahlenberg, R. Tessadri, J. Wieser, and U.J. Griesser Cryst. Growth Des. 9 2009 1054 1065
12. M.R. Caira, G. Bettinetti, and M. Sorrenti J. Pharm. Sci. 91 2002 467 481
13. A. Othman, J.S.O. Evans, I.R. Evans, R.K. Harris, and P. Hodgkinson J. Pharm. Sci. 96 2007 1380 1397
14. H. Mimura, S. Kitamura, T. Kitagawa, and S. Kohda Colloids Surf. B 26 2002 397 406
15. B.J. Murphy, M.J. Casteel, B. Samas, and J.F. Krzyzaniak J. Pharm. Sci. 101 2012 1486 1495
16. G. Stephenson, E. Groleau, R. Kleemann, W. Xu, and D. Rigsbee J. Pharm. Sci. 87 1998 536 542
17. S. Byard, A. Abraham, P.J.T. Boulton, R.K. Harris, and P. Hodgkinson J. Pharm. Sci. 101 2012 176 186
18. A. Actins, R. Arajs, S. Belakovs, L. Orola, and M. Veidis J. Chem. Crystallogr. 38 2008 169 174
19. M. Azibi, M. Draguet-Brughmas, and R. Bouche Pharm. Acta Helv. 57 1982 182 188
20. A. Běrziņš, E. Skarbulis, T. Rekis, and A. Actiņš Cryst. Growth Des. 14 2014 2654 2664
21. N.M. Blaton, O.M. Peeters, and C.J. De Ranter Acta Crystallogr. Sect. B 36 1980 2828 2830
22. L. Orola Synthesis, structure and properties of crystalline forms of some active pharmaceutical ingredients (Ph.D. thesis) 2010 Riga Technical University Riga
23. C.L. Klein, J. Welch, and L.C. Southall Acta Crystallogr. Sect. C 45 1989 650 653
24. F.G. Vogt Futur. Med. Chem. 2 2010 915 921
25. M. Geppi, G. Mollica, S. Borsacchi, and C.A. Veracini Appl. Spectrosc. Rev. 43 2008 202 302
26. R.K. Harris J. Pharm. Pharmacol. 59 2007 225 239
27. R.K. Harris Analyst 131 2006 351 373
28. P.A. Tishmack, D.E. Bugay, and S.R. Byrn J. Pharm. Sci. 92 2003 441 474
29. E. Carignani, S. Borsacchi, and M. Geppi J. Phys. Chem. A 115 2011 8783 8790
30. D.C. Apperley, A.F. Markwell, I. Frantsuzov, A.J. Ilott, R.K. Harris, and P. Hodgkinson Phys. Chem. Chem. Phys. 15 2013 6422 6430
31. P. Hodgkinson R.K. Harris, R.E. Wasylishen, M.J. Duer, NMR Crystallography 2009 Wiley Chichester
32. F.G. Vogt, D.E. Cohen, J.D. Bowman, G.P. Spoors, G.E. Zuber, G.A. Trescher, P.C. Dell'Orco, L.M. Katrincic, C.W. Debrosse, and R. Curtis Haltiwanger J. Pharm. Sci. 94 2005 651 665
33. F.G. Vogt, R.C.B. Copley, R.L. Mueller, G.P. Spoors, T.N. Cacchio, R.A. Carlton, L.M. Katrincic, J.M. Kennady, S. Parsons, and O.V. Chetina Cryst. Growth Des. 10 2010 2713 2733
34. R.K. Harris, P.Y. Ghi, H. Puschmann, D.C. Apperley, U.J. Griesser, R.B. Hammond, C. Ma, K.J. Roberts, G.J. Pearce, J.R. Yates, and C.J. Pickard Org. Process Res. Dev. 9 2005 902 910
35. J. Ruiz, V. Rodriguez, N. Cutillas, A. Hoffmann, A.-C. Chamayou, K. Kazmierczak, and C. Janiak CrystEngComm 10 2008 1928 1938
36. R.K. Harris, P. Hodgkinson, T. Larsson, A. Muruganantham, I. Ymén, D.S. Yufit, and V. Zorin Cryst. Growth Des. 8 2008 80 90
37. D.C. Apperley, A.F. Markwell, R.K. Harris, and P. Hodgkinson Magn. Reson. Chem. 50 2012 680 690
38. G.A. Stephenson, J.G. Stowell, P.H. Toma, D.E. Dorman, J.R. Greene, and S.R. Byrn J. Am. Chem. Soc. 116 1994 5766 5773
39. F.G. Vogt, P.C. Dell'Orco, A.M. Diederich, Q. Su, J.L. Wood, G.E. Zuber, L.M. Katrincic, R.L. Mueller, D.J. Busby, and C.W. DeBrosse J. Pharm. Biomed. Anal. 40 2006 1080 1088
40. R.L. Te, U.J. Griesser, K.R. Morris, S.R. Byrn, and J.G. Stowell Cryst. Growth Des. 3 2003 997 1004
41. P. Chakravarty, R.T. Berendt, E.J. Munson, V.G. Young, R. Govindarajan, and R. Suryanarayanan J. Pharm. Sci. 99 2010 816 827
42. F. Kang, F.G. Vogt, J. Brum, R. Forcino, R.C.B. Copley, G. Williams, and R. Carlton Cryst. Growth Des. 12 2011 60 74
43. S.M. Reutzel, and V.A. Russell J. Pharm. Sci. 87 1998 1568 1571
44. D.C. Apperley, P.A. Basford, C.I. Dallman, R.K. Harris, M. Kinns, P.V. Marshall, and A.G. Swanson J. Pharm. Sci. 94 2005 516 523
45. A. Findlay, and R.K. Harris J. Magn. Reson. 87 1990 605 609
46. V. Zorin, Gsim - a visualisation and processing program for solid-state NMR, URL: 〈http://gsim.sourceforge.net〉, 2013.
47. P. Hodgkinson, pNMRsim: a general simulation program for large problems in solid-state NMR, URL: 〈http://www.dur.ac.uk/paul.hodgkinson/pNMRsim〉, 2013.
48. C.J. Pickard, and F. Mauri Phys. Rev. B 63 2001 245101
49. S.J. Clark, M.D. Segall, C.J. Pickard, P.J. Hasnip, M.I. Probert, K. Refson, and M.C. Payne Z. Kristallogr. 220 2005 567 570
50. R.K. Harris, P. Hodgkinson, C.J. Pickard, J.R. Yates, and V. Zorin Magn. Reson. Chem. 45 2007 S174 S186
51. J.R. Yates, C.J. Pickard, and F. Mauri Phys. Rev. B 76 2007 024401
52. J.P. Perdew, K. Burke, and M. Ernzerhof Phys. Rev. Lett. 77 1996 3865 3868
53. A. Tkatchenko, and M. Scheffler Phys. Rev. Lett. 102 2009 073005
54. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A.J. Montgomery, J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, 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, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09 2009 Gaussian Inc. Wallingford, CT
55. Y. Zhao, and D. Truhlar Theor. Chem. Acc. 120 2008 215 241
56. M. Dračínský, and P. Hodgkinson Chem. Eur. J. 20 2014 2201 2207
57. A.J. Robbins, W.T.K. Ng, D. Jochym, T.W. Keal, S.J. Clark, D.J. Tozer, and P. Hodgkinson Phys. Chem. Chem. Phys. 9 2007 2389 2396
58. A.S. Tatton, T.N. Pham, F.G. Vogt, D. Iuga, A.J. Edwards, and S.P. Brown Mol. Pharm. 10 2013 999 1007
59. W.P. Rothwell, and J.S. Waugh J. Chem. Phys. 74 1981 2721 2732
60. A.J. Horsewill Prog. Nucl. Magn. Reson. Spectrosc. 35 1999 359 389
61. M. Dracinsky, and P. Hodgkinson CrystEngComm 15 2013 8705 8712
62. R.R. Vold, in: R. Tycko (Ed.), Nuclear Magnetic Resonance Probes of Molecular Dynamics, 1994, pp. 27-112.
63. G. Soda, and T. Chiba J. Chem. Phys. 50 1969 439 455
64. T. Chiba, and G. Soda Bull. Chem. Soc. Jpn. 44 1971 1703 1704
65. N.H.M. Hogg, P.J.T. Boulton, V.E. Zorin, R.K. Harris, and P. Hodgkinson Chem. Phys. Lett. 475 2009 58 63