Crystal Structure and Non-Hydrostatic Stress-Induced Phase Transition of Urotropine Under High Pressure.
Hirshfeld atom refinement
IR spectroscopy
X-ray diffraction
high-pressure chemistry
urotropine
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
13 Jan 2021
13 Jan 2021
Historique:
received:
26
08
2020
pubmed:
24
10
2020
medline:
24
10
2020
entrez:
23
10
2020
Statut:
ppublish
Résumé
High-pressure behavior of hexamethylenetetramine (urotropine) was studied in situ using angle-dispersive single-crystal synchrotron X-ray diffraction (XRD) and Fourier-transform infrared absorption (FTIR) spectroscopy. Experiments were conducted in various pressure-transmitting media to study the effect of deviatoric stress on phase transformations. Up to 4 GPa significant damping of molecular librations and atomic thermal motion was observed. A first-order phase transition to a tetragonal structure was observed with an onset at approximately 12.5 GPa and characterized by sluggish kinetics and considerable hysteresis upon decompression. However, it occurs only in non-hydrostatic conditions, induced by deviatoric or uniaxial stress in the sample. This behavior finds analogies in similar cubic crystals built of highly symmetric cage-like molecules and may be considered a common feature of such systems. DFT computations were performed to model urotropine equation of state and pressure dependence of vibrational modes. The first successful Hirshfeld atom refinements carried out for high-pressure diffraction data are reported. The refinements yielded more realistic C-H bond lengths than the independent atom model even though the high-pressure diffraction data are incomplete.
Identifiants
pubmed: 33095457
doi: 10.1002/chem.202003928
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
1094-1102Subventions
Organisme : Wroclawskie Centrum Sieciowo-Superkomputerowe, Politechnika Wroclawska (PL)
ID : 260
Organisme : European Synchrotron Radiation Facility
ID : CH4707, CH5087
Organisme : Ministerstwo Nauki i Szkolnictwa Wyższego
ID : DIR/WK/2016/19
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
T. C. W. Mak, F.-C. Mok, J. Cryst. Mol. Struct. 1978, 8, 183-191.
F. Pertlik, Czech. J. Phys. 1978, 28, 170-176.
P. Roose, K. Eller, E. Henkes, R. Rossbacher, H. Höke in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2015, pp. 1-55.
G. Briani, N. Fray, H. Cottin, Y. Benilan, M.-C. Gazeau, S. Perrier, Icarus 2013, 226, 541-551.
Static Compression of Energetic Materials (Eds.: S. M. Peiris, G. J. Piermarini), Springer, Berlin, 2008.
R. G. Dickinson, A. L. Raymond, J. Am. Chem. Soc. 1923, 45, 22-29.
H. W. Gonell, H. Mark, Z. Phys. Chem. 1923, 107U, 181-218.
C. E. Nordman, D. L. Schmitkons, Acta Crystallogr. 1965, 18, 764-767.
T. Yildirim, P. M. Gehring, D. A. Neumann, P. E. Eaton, T. Emrick, Phys. Rev. Lett. 1997, 78, 4938-4941.
C. P. Brock, J. D. Dunitz, Chem. Mater. 1994, 6, 1118-1127.
I. L. Karle, J. Karle, J. Am. Chem. Soc. 1965, 87, 918-920.
T. E. Jenkins, A. R. Bates, J. Phys. C: Solid State Phys. 1979, 12, 1003-1010.
P. A. Guńka, K. F. Dziubek, A. Gładysiak, M. Dranka, J. Piechota, M. Hanfland, A. Katrusiak, J. Zachara, Cryst. Growth Des. 2015, 15, 3740-3745.
Z. Zhao, Q. Zeng, H. Zhang, S. Wang, S. Hirai, Z. Zeng, W. L. Mao, Phys. Rev. B 2015, 91, 184112.
V. Vijayakumar, A. B. Garg, B. K. Godwal, S. K. Sikka, Chem. Phys. Lett. 2000, 330, 275-280.
H.-T. Huang, L. Zhu, M. D. Ward, B. L. Chaloux, R. Hrubiak, A. Epshteyn, J. V. Badding, T. A. Strobel, J. Phys. Chem. Lett. 2018, 9, 2031-2037.
S. H. Bertz, G. A. Kourouklis, A. Jayaraman, G. Lannoye, J. M. Cook, Can. J. Chem. 1993, 71, 352-357.
F. Yang, Y. Lin, J. E. P. Dahl, R. M. K. Carlson, W. L. Mao, J. Chem. Phys. 2014, 141, 154305.
J. A. Sans, F. J. Manjón, C. Popescu, V. P. Cuenca-Gotor, O. Gomis, A. Muñoz, P. Rodríguez-Hernández, J. Contreras-García, J. Pellicer-Porres, A. L. J. Pereira, D. Santamaría-Pérez, A. Segura, Phys. Rev. B 2016, 93, 054102.
A. Grzechnik, J. Solid State Chem. 1999, 144, 416-422.
A. L. J. Pereira, L. Gracia, D. Santamaría-Pérez, R. Vilaplana, F. J. Manjón, D. Errandonea, M. Nalin, A. Beltrán, Phys. Rev. B 2012, 85, 174108.
L. N. Becka, D. W. J. Cruickshank, E. G. Cox, Proc. R. Soc. London Ser. A 1963, 273, 435-454.
S. P. Kampermann, T. M. Sabine, B. M. Craven, R. K. McMullan, Acta Crystallogr. Sect. A 1995, 51, 489-497.
R. Rao, T. Sakuntala, S. K. Deb, A. P. Roy, V. Vijayakumar, B. K. Godwal, S. K. Sikka, Chem. Phys. Lett. 1999, 313, 749-754.
T. Ito, Acta Crystallogr. Sect. B 1973, 29, 364-365.
A. Celeste, F. Borondics, F. Capitani, High Pressure Res. 2019, 39, 608-618.
S. Klotz, J.-C. Chervin, P. Munsch, G. L. Marchand, J. Phys. D 2009, 42, 075413.
R. J. Angel, M. Bujak, J. Zhao, G. D. Gatta, S. D. Jacobsen, J. Appl. Crystallogr. 2007, 40, 26-32.
S. Duwal, C.-S. Yoo, J. Phys. Chem. C 2016, 120, 5101-5107.
L. Zhang, Y.-H. Li, Y.-Q. Gu, L.-C. Cai, Sci. Rep. 2019, 9, 16889.
Y. Zhuang, L. Wu, B. Gao, Z. Cui, H. Gou, D. Zhang, S. Zhu, Q. Hu, J. Mater. Chem. C 2020, 8, 3795-3799.
V. I. Levitas, J. Phys. Condens. Matter 2018, 30, 163001.
D. Jayatilaka, B. Dittrich, Acta Crystallogr. Sect. A 2008, 64, 383-393.
S. C. Capelli, H.-B. Bürgi, B. Dittrich, S. Grabowsky, D. Jayatilaka, IUCrJ 2014, 1, 361-379.
W. G. Fateley, N. T. McDevitt, F. F. Bentley, Appl. Spectrosc. 1971, 25, 155-173.
B. A. DeAngelis, R. E. Newnham, W. B. White, Am. Mineral. 1972, 57, 255-268.
P. Vinet, J. Ferrante, J. R. Smith, J. H. Rose, J. Phys. C Solid State Phys. 1986, 19, L467-L473.
P. Vinet, J. Ferrante, J. H. Rose, J. R. Smith, J. Geophys. Res.: Solid Earth 1987, 92, 9319-9325.
M. Woińska, S. Grabowsky, P. M. Dominiak, K. Woźniak, D. Jayatilaka, Sci. Adv. 2016, 2, e1600192.
J. Binns, K. V. Kamenev, G. J. McIntyre, S. A. Moggach, S. Parsons, IUCrJ 2016, 3, 168-179.
J. E. Bertie, M. Solinas, J. Chem. Phys. 1974, 61, 1666-1677.
W. A. Bassett, J. Phys. Condens. Matter 2006, 18, S921-S931.
P. A. Guńka, M. Hapka, M. Hanfland, M. Dranka, G. Chałasiński, J. Zachara, ChemPhysChem 2018, 19, 857-864.
H. K. Mao, J. Xu, P. M. Bell, J. Geophys. Res.: Solid Earth 1986, 91, 4673-4676.
K. Syassen, High Pressure Res. 2008, 28, 75-126.
C. Prescher, V. B. Prakapenka, High Pressure Res. 2015, 35, 223-230.
CrysAlisPro Software System Ver. 171.40.71a, Rigaku OD, Oxford, UK, 2019.
G. M. Sheldrick, Acta Crystallogr. Sect. C 2015, 71, 3-8.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Crystallogr. 2009, 42, 339-341.
A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7-13.
V. Schomaker, K. N. Trueblood, Acta Crystallogr. Sect. B 1968, 24, 63-76.
D. W. J. Cruickshank, Acta Crystallogr. 1956, 9, 757-758.
D. W. J. Cruickshank, Acta Crystallogr. 1956, 9, 754-756.
B. H. Toby, R. B. Von Dreele, J. Appl. Crystallogr. 2013, 46, 544-549.
F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
W. Kohn, L. J. Sham, Phys. Rev. 1965, 140, A1133-A1138.
R. Dovesi, R. Orlando, B. Civalleri, C. Roetti, V. R. Saunders, C. M. Zicovich-Wilson, Z. Kristallogr. 2005, 220, 571-573.
R. Dovesi, V. R. Saunders, C. Roetti, R. Orlando, C. M. Zicovich-Wilson, B. Pascale, B. Civalleri, K. Doll, N. M. Harrison, I. J. Bush, P. D'Arco, M. Llunell, CRYSTAL09, University of Torino, Torino, 2009.
M. F. Peintinger, D. V. Oliveira, T. Bredow, J. Comput. Chem. 2013, 34, 451-459.
B. Civalleri, C. M. Zicovich-Wilson, L. Valenzano, P. Ugliengo, CrystEngComm 2008, 10, 405-410.
D. D. Johnson, Phys. Rev. B 1988, 38, 12807-12813.
R. Bini, R. Ballerini, G. Pratesi, H. J. Jodl, Rev. Sci. Instrum. 1997, 68, 3154-3160.
F. A. Gorelli, L. Ulivi, M. Santoro, R. Bini, Phys. Rev. Lett. 1999, 83, 4093-4096.
M. Wojdyr, J. Appl. Crystallogr. 2010, 43, 1126-1128.