Pressure-induced phase transition in N-H⋯O hydrogen-bonded molecular crystal biurea: Combined Raman scattering and X-ray diffraction study

Journal of Physical Chemistry C

Volumn 118, Issue 28, 2014, Pages 15162-15168

  Yan, Tingting ^a   Wang, Kai ^a   Tan, Xiao ^a   Yang, Ke ^b   Liu, Bingbing ^a   Zou, Bo ^a  

^a JILIN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF APPLIED PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; MOLECULAR CRYSTALS; RAMAN SCATTERING; X RAY DIFFRACTION;

DIAMOND-ANVIL CELL; DIFFRACTION SPECTRA; FREQUENCY SHIFT CURVES; HYDROGEN BONDED NETWORK; IN-SITU RAMAN SPECTROSCOPY; PRESSURE-INDUCED PHASE TRANSITION; RAMAN SCATTERING MEASUREMENTS; X-RAY DIFFRACTION STUDIES;

RAMAN SPECTROSCOPY;

EID: 84904550562     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp503803n     Document Type: Article

References (56)

1. Steiner, T. The Hydrogen Bond in the Solid State Angew. Chem., Int. Ed. 2002, 41, 48-76 (Pubitemid 34081196)
2. Aakeröy, C. B.; Seddon, K. R. The Hydrogen Bond and Crystal Engineering Chem. Soc. Rev. 1993, 22, 397-407
3. Dunitz, J. D.; Gavezzotti, A. Molecular Recognition in Organic Crystals: Directed Intermolecular Bonds or Nonlocalized Bonding? Angew. Chem., Int. Ed. 2005, 44, 1766-1787
4. Fillaux, F. Hydrogen Bonding and Quantum Dynamics in the Solid State Int. Rev. Phys. Chem. 2000, 19, 553-564 (Pubitemid 32057799)
5. Desiraju, G. R. Hydrogen Bridges in Crystal Engineering: Interactions without Borders Acc. Chem. Res. 2002, 35, 565-573
6. Luzar, A.; Chandler, D. Hydrogen-Bond Kinetics in Liquid Water Nature 1996, 379, 55-57 (Pubitemid 126532744)
7. Wang, K.; Duan, D. F.; Wang, R.; Liu, D.; Tang, L.; Cui, T.; Liu, B. B.; Cui, Q.; Liu, J.; Zou, B. Pressure-Induced Phase Transition in Hydrogen-Bonded Supramolecular Adduct Formed by Cyanuric Acid and Melamine J. Phys. Chem. B 2009, 113, 14719-14724
8. Minkov, V. S.; Krylov, A. S.; Boldyreva, E. V.; Goryainov, S. V.; Bizyaev, S. N.; Vtyurin, A. N. Pressure-Induced Phase Transitions in Crystalline l -and dl -Cysteine J. Phys. Chem. B 2008, 112, 8851-8854
9. Mishra, A. K.; Murli, C.; Sharma, S. M. High Pressure Raman Spectroscopic Study of Deuterated γ-Glycine J. Phys. Chem. B 2008, 112, 15867-15874
10. Goryainov, S.; Boldyreva, E.; Kolesnik, E. Raman Observation of a New (Χ) Polymorph of Glycine? Chem. Phys. Lett. 2006, 419, 496-500 (Pubitemid 43220518)
11. 2O and the Transition to Symmetric Hydrogen Bonds Phys. Rev. Lett. 1999, 83, 1998
12. Bernasconi, M.; Silvestrelli, P.; Parrinello, M. Ab Initio Infrared Absorption Study of the Hydrogen-Bond Symmetrization in Ice Phys. Rev. Lett. 1998, 81 1235
13. Goncharov, A. F.; Manaa, M. R.; Zaug, J. M.; Gee, R. H.; Fried, L. E.; Montgomery, W. B. Polymerization of Formic Acid under High Pressure Phys. Rev. Lett. 2005, 94 065505
14. Yan, T. T.; Wang, K.; Tan, X.; Liu, B. B.; Zou, B. p -Aminobenzoic Acid Polymorphs under High Pressures RSC Adv. 2014, 4, 15534-15541
15. Mookherjee, M.; Stixrude, L. High-Pressure Proton Disorder in Brucite Am. Mineral. 2006, 91, 127-134
16. Kuo, J.-L.; Klein, M. L.; Kuhs, W. F. The Effect of Oroton Disorder on theStructure of Ice-Ih: A Theoretical Study J. Chem. Phys. 2005, 123 134505
17. Yan, T. T.; Li, S. R.; Wang, K.; Tan, X.; Jiang, Z. M.; Yang, K.; Liu, B. B.; Zou, G. T.; Zou, B. Pressure-Induced Phase Transition in N-H⋯O Hydrogen-Bonded Molecular Crystal Oxamide J. Phys. Chem. B 2012, 116, 9796-9802
18. Wang, K.; Duan, D. F.; Wang, R.; Lin, A.; Cui, Q.; Liu, B. B.; Cui, T.; Zou, B.; Zhang, X.; Hu, J. Z. Stability of Hydrogen-Bonded Supramolecular Architecture under High Pressure Conditions: Pressure-Induced Amorphization in Melamine- Boric Acid Adduct Langmuir 2009, 25, 4787-4791
19. Tan, X.; Wang, K.; Li, S. R.; Yuan, H. S.; Yan, T. T.; Liu, J.; Yang, K.; Liu, B. B.; Zou, G. T.; Zou, B. Exploration of the Pyrazinamide Polymorphism at High Pressure J. Phys. Chem. B 2012, 116, 14441-14450
20. Wang, K.; Liu, J.; Yang, K.; Liu, B. B.; Zou, B. High-Pressure-Induced Polymorphic Transformation of Maleic Hydrazide J. Phys. Chem. C 2014, 118, 8122-8127
21. Bastea, M.; Bastea, S.; Reaugh, J. E.; Reisman, D. B. Freezing Kinetics in Overcompressed Water Phys. Rev. B 2007, 75 172104
22. Fanetti, S.; Lapini, A.; Pagliai, M.; Citroni, M.; Di Donato, M.; Scandolo, S.; Righini, R.; Bini, R. Structure and Dynamics of Low-Density and High-Density Liquid Water at High Pressure J. Phys. Chem. Lett. 2013, 5, 235-240
23. Schwegler, E.; Galli, G.; Gygi, F. Water under Pressure Phys. Rev. Lett. 2000, 84 2429
24. Sun, C. Q.; Zhang, X.; Zheng, W. The Hidden Force Opposing Ice Compression Chem. Sci. 2012, 3, 1455-1460
25. Chen, J.-Y.; Yoo, C.-S. High Density Amorphous Ice at Room Temperature Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 7685-7688
26. Wang, Y.; Liu, H.; Lv, J.; Zhu, L.; Wang, H.; Ma, Y. High Pressure Partially Ionic Phase of Water Ice Nat. Commun. 2011, 2, 563
27. Dawson, A.; Allan, D. R.; Belmonte, S. A.; Clark, S. J.; David, W. I.; McGregor, P. A.; Parsons, S.; Pulham, C. R.; Sawyer, L. Effect of High Pressure on the Crystal Structures of Polymorphs of Glycine Cryst. Growth Des. 2005, 5, 1415-1427 (Pubitemid 41032657)
28. Boldyreva, E.; Sowa, H.; Seryotkin, Y. V.; Drebushchak, T.; Ahsbahs, H.; Chernyshev, V.; Dmitriev, V. Pressure-Induced Phase Transitions in Crystalline L-Serine Studied by Single-Crystal and High-Resolution Powder X-ray Diffraction Chem. Phys. Lett. 2006, 429, 474-478 (Pubitemid 44419397)
29. Staun Olsen, J.; Gerward, L.; Souza Filho, A.; Freire, P.; Mendes Filho, J.; Melo, F. High-Pressure X-ray Diffraction of L-ALANINE Crystal High Pressure Res. 2006, 26, 433-437
30. Wang, R.; Li, S. R.; Wang, K.; Duan, D. F.; Tang, L.; Cui, T.; Liu, B. B.; Cui, Q. L.; Liu, J.; Zou, B. Pressure-Induced Phase Transition in Hydrogen-Bonded Supramolecular Structure: Guanidinium Nitrate J. Phys. Chem. B 2010, 114, 6765-6769
31. Olejniczak, A.; Ostrowska, K.; Katrusiak, A. H-Bond Breaking in High-Pressure Urea J. Phys. Chem. C 2009, 113, 15761-15767
32. Hermet, P.; Ghosez, P. First-Principles Study of the Dynamical and Nonlinear Optical Properties of Urea Single Crystals Phys. Chem. Chem. Phys. 2010, 12, 835-843
33. Andersson, O.; Ross, R. Phase Behavior and Thermal Conductivity of Urea at Pressures up to 1 GPa and at Temperatures in the Range 50-370 K Int. J. Thermophys. 1994, 15, 513-524
34. Yang, G.; Li, Y.; Dreger, Z.; White, J.; Drickamer, H. High-Pressure Studies of Second Harmonic Generation in Organic Materials Chem. Phys. Lett. 1997, 280, 375-380 (Pubitemid 127174300)
35. 2 of Several Organic Substances Proc. Am. Acad. Arts Sci. 1938, 72, 227-268
36. Marshall, W. G.; Francis, D. J. Attainment of Near-Hydrostatic Compression Conditions Using the Paris-Edinburgh Cell J. Appl. Crystallogr. 2002, 35, 122-125 (Pubitemid 34538191)
37. Bonin, M.; Marshall, W. G.; Weber, H.-P.; Toledano, F. ISIS Pulsed Neutron and Muon Source, Annual Report 1998; Rutherford Appleton Laboratory: Didcot, U.K., 1998; pp 34-35.
38. Hamann, S. D.; Linton, M. The Influence of Pressure on the Infrared Spectra of Hydrogen-Bonded Solids. I. Compounds with OH⋯O Bonds Aust. J. Chem. 1975, 28, 2567-2578
39. Lamelas, F.; Dreger, Z.; Gupta, Y. Raman and X-ray Scattering Studies of High-Pressure Phases of Urea J. Phys. Chem. B 2005, 109, 8206-8215 (Pubitemid 40644048)
40. Figuiere, P.; Ghelfenstein, M.; Szwarc, H. First-Order Phase Diagram of Thiourea and Raman Spectroscopy Chem. Phys. Lett. 1975, 33, 99-103
41. Banerji, A.; Deb, S. Raman Scattering Study of High-Pressure Phase Transition in Thiourea J. Phys. Chem. B 2007, 111, 10915-10919 (Pubitemid 47522579)
42. Asahi, T.; Hasebe, K.; Onodera, A. Crystal Structure of the High Pressure Phase VI of Thiourea J. Phys. Soc. Jpn. 2000, 69, 2895-2899
43. Russell, P. R.; Strachan, A. N. The Thermal Decomposition of Biurea J. Chem. Soc., Perkin Trans. 2 1978, 323-326
44. Brown, D.; Russell, P. The Crystal and Molecular Structure of Biurea Acta Crystallogr. 1976, 32, 1056-1058
45. Audrieth, D. C.; Mohr, E. B. Biurea Inorg. Synth. 1953, 4, 26-28
46. Xie, Y.; Li, P.; Zhang, J.; Wang, H.; Qian, H.; Yao, W. Comparative Studies by IR, Raman, and Surface-Enhanced Raman Spectroscopy of Azodicarbonamide, Biurea and Semicarbazide Hydrochloride Spectrochim. Acta 2013, 114, 80-84
47. Kraebel, C. M.; Davis, S. M.; Landon, M. J. Hydrazine Derivatives-I. Infrared Spectra of Biureas, 1,1′-Azobisformamides and Hydrazine Disulfonic Acid Derivatives Spectrochim. Acta 1967, 23, 2541-2549
48. 2 Bull. Chem. Soc. Jpn. 1964, 37, 974-984
49. Park, T.-R.; Dreger, Z. A.; Gupta, Y. M. Raman Spectroscopy of Pentaerythritol Single Crystals under High Pressures J. Phys. Chem. B 2004, 108, 3174-3184
50. Ciezak, J. A.; Jenkins, T. A.; Liu, Z.; Hemley, R. J. High-Pressure Vibrational Spectroscopy of Energetic Materials: Hexahydro-1,3,5-trinitro-1,3,5- triazine J. Phys. Chem. A 2007, 111, 59-63 (Pubitemid 46277948)
51. Rao, R.; Sakuntala, T.; Godwal, B. Evidence for High-Pressure Polymorphism in Resorcinol Phys. Rev. B 2002, 65 054108
52. Franco, O.; Orgzall, I.; Regenstein, W.; Schulz, B. Structural and Spectroscopical Study of a 2,5-Diphenyl-1, 3, 4-oxadiazole Polymorph under Compression J. Phys.: Condens. Matter 2006, 18 1459
53. Hamann, S. D.; Linton, M. The Influence of Pressure on the Infrared Spectra of Hydrogen-Bonded Solids. III. Compounds with NH⋯X Bonds Aust. J. Chem. 1976, 29, 1641-1647
54. Reynolds, J.; Sternstein, S. S. Effect of Pressure on the Infrared Spectra of Some Hydrogen-Bonded Solids J. Chem. Phys. 2004, 41, 47-50
55. Pravica, M.; Yulga, B.; Liu, Z.; Tschauner, O. Infrared Study of 1,3,5-triamino-2,4,6-Trinitrobenzene under High Pressure Phys. Rev. B 2007, 76 064102
56. Moon, S.; Drickamer, H. Effect of Pressure on Hydrogen Bonds on Organic Solids J. Chem. Phys. 2003, 61, 48-54