The Role of Hydrogen Bonds in the Pressure-Induced structural Distortion of 4-Hydroxyacetanilide Crystals

Boldyreva, E.; Shakhtshneider, T. P.; Ahsbabs, H.; Uchtmann, H.; Burgina, E. B.; Baltakhinov, V. P.

Artykuł - szczegóły

Tytuł artykułu

The Role of Hydrogen Bonds in the Pressure-Induced structural Distortion of 4-Hydroxyacetanilide Crystals

Autorzy

Boldyreva E. , Shakhtshneider T. P. , Ahsbabs H. , Uchtmann H. , Burgina E. B. , Baltakhinov V. P.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

Results of X-ray diffraction and IR-specroscopy studies of the role of hydrogen bonds in the structural distortion of the monoclinic and the orthorhombic polymorphs of paracetamol induced by hydrostatic pressure (up to 4-5 GPa) are analyzed. Two groups of phenomena were studied: (i) the anisotropic structural distortion of the same polymorph, (ii) transitions between the polymorphs induced by pressure. The bulk compressibilities of the two polymorphs are practically equal. The anisotropy of pressure-induced structural distortion is qualitatively different. Lattice expansion in particular crystallographic directions was observed for the monoclinic polymorph. With increasing pressure the intermolecular NH...O and OH...O hydrogen bonds contracted and the intramolecular angles between the planes of the phenyl ring and the acetamide group decreased. Pressure- induced transitions between the polymorphs were poorly reproducible and limited by nucleation of the new polymorph.

Słowa kluczowe

hydrogen bonds paracetamol p-hydroxyacetanilide acetaminophen diamond anvil cell high pressure crystallography high pressure IR-spectroscopy polymorphic transitions polymorphs

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2002

Tom

Vol. 76 / nr 9

Strony

1333--1346

Opis fizyczny

Bibliogr. 47 poz., rys.

Twórcy

autor

Boldyreva E.

boldyrev@nsu.ru

Novosibirsk State University, Institute of Solid State Chemistry and Mechanochemistry, ul, Kutateladze 18, Novosibirsk 128, 630128, Russia

autor

Shakhtshneider T. P.

Novosibirsk State University, Institute of Solid State Chemistry and Mechanochemistry, ul, Kutateladze 18, Novosibirsk 128, 630128, Russia

autor

Ahsbabs H.

Philipps University of Marburg, Hans-Meerwein Strasse, 35032 Marburg/Lahn, Germany

autor

Uchtmann H.

Philipps University of Marburg, Hans-Meerwein Strasse, 35032 Marburg/Lahn, Germany

autor

Burgina E. B.

Boreskov Institute of Catalysis, pr. Lavrent ’eva 5, Novosibirsk 90, 630090, Russia

autor

Baltakhinov V. P.

Boreskov Institute of Catalysis, pr. Lavrent ’eva 5, Novosibirsk 90, 630090, Russia

Bibliografia

1. Pimentel G.C. and McClellan A.L., The Hydrogen Bond, San Francisco 1960: W. H. Freeman.
2. Jeffrey G.A. and Saenger W., Hydrogen Bonding in Biological Structures, Berlin 1991: Springer-Verlag.
3. Jeffrey G.A., An Introduction to Hydrogen Bonding, NY 1997: Oxford University Press.
4. Desiraju G.R. and Steiner T., The Weak Hydrogen Bond, Oxford 1999; Oxford Science Publications.
5. Ubbelohde A.R., Proc. Royal Soc. London Ser. A, 173,417 (1939),
6. Ubbelohde A.R. and Woodward I., Proc. Royal Soc. London Ser. A, 185,448 (1946).
7. Dunitz J.D., Mol. Cryst. Liq. Cry St., 279, 209 (1996).
8. Katrusiak A. andNelmes R.J., J. Phys. C: Solid State Phys., 19, L765 (1986).
9. Katrusiak A., Acta Cryst., B46, 246 (1990).
10. Katrusiak A., High Press. Res., 6,265 (1991).
11. Katrusiak A., High Press. Res., 6, 155 (1991).
12. Katrusiak A., Cryst Res. Techn., 26, 523 (1991).
13. Katrusiak A., Acta Cryst., B51, 873 (1995).
14. Boldyreva E.V., Burgina E.B., Baltakhinov V.P., Burleva L.P., Ahsbahs H., Uchtmann H. and Dulepov V.E., Ber. Bunsenges. Phys. Chem., 96, 931 (1992).
15. Boldyreva E.V., Ahsbahs H. and Uchtmann H., Ber. Bunsenges. Phys. Chem., 98, 738 (1994).
16. Boldyreva E.V., Kusmina S.L. and Ahsbahs H., Zh. Strukt. Khim, (Russian J. Struct. Chem.), 39, 424 (1998).
17. Boldyreva E.V., Naumov D.Y. and Ahsbahs R, Acta Cryst., B54, 798 (1998).
18. Boldyreva E.V., Ahsbahs H,, Naumov D.Y and Kutoglu A., Acta Cryst., C54,1378 (1998).
19. Boldyreva E.V., Kusmina S.L., Novikov P.B. and Ahsbahs H„ Zh. Strukt. Khim., (Russian J. Struct. Chem.), 40, 1110(1999).
20. Boldyreva E.V., In: Reactivity of Molecular Solids, Eds. E.V. Boldyreva, V.V. Boldyrev, Chichester 1999: Wiley, p. 1.
21. Boldyreva E.V., Ahsbahs H., Kashcheeva N.E. and Uchtmann H.t High Press. Res., 17, 79 (2000).
22. Boldyreva E.V., Shakhtshneider T.P., Vasilchenko M.A., Ahsbahs H. and Uchtmann H., Acta Cryst., B56, 299 (2000).
23. Boldyreva E.V., Shakhtshneider T.P., Ahsbahs H., Sowa H. and Uchtmann H., J. Therm. Analys., 66, ? (2002).
24. Boldyreva E.V., Shakhtshneider T.P., Ahsbahs H. and Uchtmann H., Zh. Strukt. Khim. (Russian J. Struct. Chem.), 43,107 (2002).
25. Merck Index, 2000-2001, 822325.
26. http://www.pharmweb.net/pwmirror/pwy/paracetamol
27. Fairbrother J.E., In Analytical Profiles of Drug Substances, Ed. K. Florey, Vol. 3, pp. 1. N.Y. 1974: Acad. Press.
28. Haisa M., Kashino S. and Maeda H., Acta Cryst., B30, 2510 (1974).
29. Haisa M., Kashino S., Kawai R. and Maeda H., Acta Cryst., B32, 1283 (1976).
30. Nichols G. and Frampton C.S., J. Pharm. Sei., 87, 684 (1998).
31. Naumov D.Y., Vasilchenko M.A. and Howard J.A.K., Ada Cryst., C54, 653 (1998).
32. Forman R.A., Piermarini G.J., Barnett J.D. and Block S., Science, 176, 284 (1972).
33. Piermarini G.J.,BlockS., Barnett J.D. and Forman R.A., J. Appl. Phys., 46, 2774 (1975).
34. Kutoglu A., MDIF4. Computer software for high-pressure data collection at a STOE four-circle diffractometer, Marburg University, Germany (1997).
35. Binev I.G., Vassileva-Boyadjieva P. and Binev Y.I., J. Mol. Struct., 447,235 (1998).
36. Marti E., Kaisersberger E. and Kaiser G., Eds,, Thermoanalytical Characterization of Pharmaceuticals, Netzsch Annual 2000, Netzsch-Geraetebau GmbH, 12, Selb, p. 29 (2000).
37. DiMartino P., Guyot-Hermann A.-M., Conflant P., Drache M. and Guyot J.-C., Int. J. Pharm., 128, 1 (1996).
38. VonNuemberg E. and Hopp A., Pharm. Ind., 44, 1081 (1982).
39. de Wet F.N., Gerber J. J., Loetter A.P., van derWatt J.G. and Dekker T.G., Drug Develop. Industr. Pharm., 24,447 (1998).
40. Kuhnert-Brandstaetter M., Thermomicroscopy in the Analysis of Pharmaceuticals, Oxford 1971: Pergamon Press.
41. Buerger A., Acta Pharm. Techno!., 28, 1 (1982).
42. Conflant P. and Guyot-Hermann A.-M., Eur. J. Pharm. Biopharm., 40, 388 (1994).
43. Barra J., Kubel F. and Doelker E., Proceed. 3rd Symposium on Pharmacy and Thermal Analysis, Ascona, Switzerland, 2 PO (1997).
44. DiMartino P., Conflant P., Drache M., Huvenne J.-P. and Guyot-Hermann A.-M., J. Therm. Analys., 48, 447(1997).
45. Cianferani S., Hard A.P., Hofmeier U.C., Marcolli C., Szelagiewicz M. and Zilian A., Book of Abstracts. PhandTA4, Karlsruhe, Germany (1999).
46. Cianferani S., Szelaz M., Walter S. and Marti E,, Book of Abstracts 23rd Annual Calorimetrie et d'Analyse Thermique (AFCAI), Bale Meeting, Switzerland (1998).
47. Politov A.A., Kostrovsky V.G. and Boldyrev V.V., Russ. J. Phys. Chem., 75, 2062 (2001). Polish J. Chem., 76, 1347-1361 (2002)

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ1-0023-0046