The European Physical Journal Special Topics

, Volume 226, Issue 5, pp 849–855 | Cite as

A new polymorph of 4′-hydroxyvalerophenone revealed by thermoanalytical and X-ray diffraction studies

  • Cátia S. D. Lopes
  • Carlos E. S. Bernardes
  • M. Fátima M. Piedade
  • Hermínio P. Diogo
  • Manuel E. Minas da Piedade
Regular Article
Part of the following topical collections:
  1. Phase Equilibria and Their Applications

Abstract

A new polymorph of 1-(4-hydroxyphenyl)pentan-1-one (4′-hydroxyvalerophenone, HVP) was identified by using differential scanning calorimetry, hot stage microscopy, and X-ray powder diffraction. This novel crystal form (form II) was obtained by crystallization from melt. It has a fusion temperature of T fus = 324.3 ± 0.2 K and an enthalpy of fusion Δfus H m o = 18.14±0.18 kJ·mol−1. These values are significantly lower than those observed for the previously known phase (form I, monoclinic, space group P21/c, T fus = 335.6 ± 0.7 K; Δfus H m o = 26.67±0.04 kJ·mol−1), which can be prepared by crystallization from ethanol. The results here obtained, therefore, suggest that form I is thermodynamically more stable than the newly identified form II and, furthermore, that the two polymorphs are monotropically related.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    F. Iwasaki, Acta Crystallogr. B33, 1646 (1977)CrossRefGoogle Scholar
  2. 2.
    J.P. Jasinski, R.J. Butcher, B. Narayana, M.T. Swany, H.S. Yathirajan, Acta Crystallogr. E64, o187 (2008)Google Scholar
  3. 3.
    C.E.S. Bernardes, M.F.M. Piedade, M.E. Minas da Piedade, Cryst. Growth Des. 8, 2419 (2008)CrossRefGoogle Scholar
  4. 4.
    B.K. Vainshtein, G.M. Lobanova, G.V. Gurskaya, Kristallografiya 19, 531 (1974)Google Scholar
  5. 5.
    S. Chenthamarai, D. Jayaraman, K. Meera, P. Santhanaraghavan, C. Subramanian, G. Bocelli, P. Ramasamy, Crystal Eng. 4, 37 (2001)CrossRefGoogle Scholar
  6. 6.
    A.J. Kresge, A.J. Lough, Y. Zhu, Acta Crystallogr. 58, o1057 (2002)CrossRefGoogle Scholar
  7. 7.
    C.E.S. Bernardes, M.E. Minas da Piedade, Cryst. Growth Des. 12, 2932 (2012)CrossRefGoogle Scholar
  8. 8.
    C.E.S. Bernardes, M.F.M. Piedade, M.E. Minas da Piedade, Cryst. Growth Des. 10, 3070 (2010)CrossRefGoogle Scholar
  9. 9.
    C.E.S. Bernardes, M.L.S. Matos Lopes, J.R. Ascenso, M.E. Minas da Piedade, Cryst. Growth Des. 14, 5436 (2014)CrossRefGoogle Scholar
  10. 10.
    B. Xu, Z.Q. Feng, J.T. Wang, L.G. Hu, J. Huang, Acta Crystallogr. E62, O2603 (2006)Google Scholar
  11. 11.
    Z.H. Luo, H.J. Zhu, S. Liu, Acta Crystallogr. E62, O5054 (2006)Google Scholar
  12. 12.
    F.H. Allen, Acta Crystallogr. B58, 380 (2002)CrossRefGoogle Scholar
  13. 13.
    J. Bernstein, Polymorphism in Molecular Crystals (Oxford University Press, Oxford, 2002)Google Scholar
  14. 14.
    H.G. Brittain, Polymorphism in Pharmaceutical Solids (Marcel Dekker, New York, 1999)Google Scholar
  15. 15.
    H.G. Brittain, J. Pharm. Sci. 96, 705 (2007)CrossRefGoogle Scholar
  16. 16.
    R. Hilfiker, Polymorphism in the Pharmaceutical Industry (Wiley-VCH Verlag GmbH & Co., Weinheim, 2006)Google Scholar
  17. 17.
    C.S.D. Lopes, F. Agapito, C.E.S. Bernardes, M.E. Minas da Piedade, J. Chem. Thermodyn. 104, 281 (2017)CrossRefGoogle Scholar
  18. 18.
    J. Meija, T.B. Coplen, M. Berglund, W.A. Brand, P. De Bièvre, M. Gröning, N.E. Holden, J. Irrgeher, R.D. Loss, T. Walczyk, T. Prohaska, Pure Appl. Chem. 88, 265 (2016)Google Scholar
  19. 19.
    C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, P.A. Wood, J. Appl. Crystallogr. 41, 466 (2008)CrossRefGoogle Scholar
  20. 20.
    A. Burger, R. Ramberger, Mikrochim. Acta 2, 259 (1979)CrossRefGoogle Scholar
  21. 21.
    R.G. Simões, C.E.S. Bernardes, M.E. Minas da Piedade, Cryst. Growth Des. 13, 2803 (2013)CrossRefGoogle Scholar

Copyright information

© EDP Sciences and Springer 2017

Authors and Affiliations

  1. 1.Centro de Química e Bioquímica e Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de LisboaLisboaPortugal
  2. 2.Centro de Química Estrutural, Instituto Superior Técnico, Universidade de LisboaLisboaPortugal

Personalised recommendations