X-ray Raman scattering: a new in situ probe of molecular structure during nucleation and crystallization from liquid solutions

Al-Madhagi, Laila H.; Chang, Sin-Yuen; Balasubramanian, Mahalingam; Kroner, Anna B.; Shotton, Elizabeth J.; Willneff, Elizabeth A.; Mishra, Bhoopesh; Schroeder, Sven L. M.

doi:10.1039/C8CE00929E

Title: X-ray Raman scattering: a new in situ probe of molecular structure during nucleation and crystallization from liquid solutions

Journal Article · Mon Nov 05 00:00:00 EST 2018 · CrystEngComm

DOI:https://doi.org/10.1039/C8CE00929E· OSTI ID:1474755

^[1];

^[2];

^[3]; Kroner, Anna B. ^[2];

^[2]; Willneff, Elizabeth A. ^[4]; Mishra, Bhoopesh ^[5];

^[1]

School of Chemical and Process Engineering, University of Leeds, Leeds LS2 9JT, UK, Diamond Light Source Ltd.
Diamond Light Source Ltd., Didcot, UK
Advanced Photon Source, Argonne National Laboratory, Argonne, USA
School of Design, The University of Leeds, Leeds LS2 9JT, UK
School of Chemical and Process Engineering, University of Leeds, Leeds LS2 9JT, UK, Department of Physics

X-ray Raman scattering (XRS) has been used for in situ probing of solute molecule speciation in solution during cooling crystallization. The C and N K-edges of aqueous imidazole were measured as a function of temperature to monitor the transition from the undersaturated state through supersaturation to crystallization. A new jacketed-vessel crystallizer with internal flow was used, which enables thermal control and minimizes radiation damage. We have demonstrated that the C and N K-edges of imidazole are sensitive to changes in local bonding. In line with this, an abrupt change in the N K-edge fine structure indicates the onset of desolvation and crystallization from the supersaturated solution. In contrast, negligible changes are observed in the C and N K-edge spectra acquired during cooling, indicating that the average solvation structure around imidazole molecules does not change significantly while traversing the thermodynamically metastable supersaturated zone. To the best of our knowledge this is the first time X-ray Raman scattering has been used for studying molecular speciation in organic aqueous solutions during crystallization. Time-dependent density functional theory (TD-DFT) calculations of the near-edge spectra were performed using implicit, explicit and combined solvation models to elucidate the likely binding sites of the water molecules. An explicit solvation model with one water molecule coordinating each nitrogen moiety in the imidazole ring accurately reproduces the peak positions and intensities of the XRS spectra of aqueous imidazole solution.

View Journal Article

Cite

Export

Save

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE; AstraZeneca PLC.; Diamond Light Source, UK

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1474755

Alternate ID(s):: OSTI ID: 1486882

Journal Information:: CrystEngComm, Journal Name: CrystEngComm Vol. 20 Journal Issue: 43; ISSN 1466-8033

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

Citation Metrics:

Cited by: 6 works

Citation information provided by
Web of Science

References (70)

The Relationship between Solution Structure and Crystal Nucleation: A Neutron Scattering Study of Supersaturated Methanolic Solutions of Benzoic Acid Burton, R. C.; Ferrari, E. S.; Davey, R. J. The Journal of Physical Chemistry B, Vol. 114, Issue 26 https://doi.org/10.1021/jp103099j	journal	July 2010
ATHENA , ARTEMIS , HEPHAESTUS : data analysis for X-ray absorption spectroscopy using IFEFFIT Ravel, B.; Newville, M. Journal of Synchrotron Radiation, Vol. 12, Issue 4 https://doi.org/10.1107/S0909049505012719	journal	June 2005
Imidazole, a New Tunable Reagent for Producing Nanocellulose, Part I: Xylan-Coated CNCs and CNFs Mao, Jia; Abushammala, Hatem; Hettegger, Hubert Polymers, Vol. 9, Issue 12 https://doi.org/10.3390/polym9100473	journal	September 2017
Nucleation of NaCl from Aqueous Solution: Critical Sizes, Ion-Attachment Kinetics, and Rates Zimmermann, Nils E. R.; Vorselaars, Bart; Quigley, David Journal of the American Chemical Society, Vol. 137, Issue 41 https://doi.org/10.1021/jacs.5b08098	journal	October 2015
Self-association of organic solutes in solution: a NEXAFS study of aqueous imidazole Thomason, M. J.; Seabourne, C. R.; Sattelle, B. M. Faraday Discussions, Vol. 179 https://doi.org/10.1039/C5FD00005J	journal	January 2015
X-Ray Raman Spectroscopic Study of Water in the Condensed Phases Tse, John S.; Shaw, Dawn M.; Klug, Dennis D. Physical Review Letters, Vol. 100, Issue 9 https://doi.org/10.1103/PhysRevLett.100.095502	journal	March 2008
The ORCA program system: The ORCA program system Neese, Frank Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 2, Issue 1 https://doi.org/10.1002/wcms.81	journal	June 2011
Molecular aggregation phenomena in solution: an energy dispersive X-ray diffraction study of concentrated imidazole water solutions Gontrani, Lorenzo; Caminiti, Ruggero; Bencivenni, Luigi Chemical Physics Letters, Vol. 301, Issue 1-2 https://doi.org/10.1016/S0009-2614(99)00005-6	journal	February 1999
Detection and characterisation of sub-critical nuclei during reactive Pd metal nucleation by X-ray absorption spectroscopy Chang, S. -Y.; Gründer, Y.; Booth, S. G. CrystEngComm, Vol. 18, Issue 5 https://doi.org/10.1039/C5CE01883H	journal	January 2016
NEXAFS Sensitivity to Bond Lengths in Complex Molecular Materials: A Study of Crystalline Saccharides Gainar, Adrian; Stevens, Joanna S.; Jaye, Cherno The Journal of Physical Chemistry B, Vol. 119, Issue 45 https://doi.org/10.1021/acs.jpcb.5b07159	journal	November 2015
The LERIX User Facility Seidler, G. T.; Fister, T. T.; Cross, J. O. X-RAY ABSORPTION FINE STRUCTURE - XAFS13: 13th International Conference, AIP Conference Proceedings https://doi.org/10.1063/1.2644702	conference	January 2007
In situ XAFS Study of Palladium Electrodeposition at the Liquid/Liquid Interface Booth, Samuel G.; Chang, Sin-Yuen; Uehara, Akihiro Electrochimica Acta, Vol. 235 https://doi.org/10.1016/j.electacta.2017.03.059	journal	May 2017
Intermolecular bonding of hemin in solution and in solid state probed by N K-edge X-ray spectroscopies Golnak, Ronny; Xiao, Jie; Atak, Kaan Physical Chemistry Chemical Physics, Vol. 17, Issue 43 https://doi.org/10.1039/C5CP04529K	journal	January 2015
Solubilities, Partition Coefficients, Density, and Surface Tension for Imidazoles + Octan-1-ol or + Water or + n -Decane ^† Domańska, Urszula; Kozłowska, Marta Karolina; Rogalski, Marek Journal of Chemical & Engineering Data, Vol. 47, Issue 3 https://doi.org/10.1021/je0103014	journal	May 2002
Pseudoequivalent Nitrogen Atoms in Aqueous Imidazole Distinguished by Chemical Shifts in Photoelectron Spectroscopy Nolting, Dirk; Ottosson, Niklas; Faubel, Manfred Journal of the American Chemical Society, Vol. 130, Issue 26 https://doi.org/10.1021/ja8022384	journal	July 2008
Femtosecond X-ray protein nanocrystallography Chapman, Henry N.; Fromme, Petra; Barty, Anton Nature, Vol. 470, Issue 7332, p. 73-77 https://doi.org/10.1038/nature09750	journal	February 2011
Determination of intramolecular bond lengths in gas phase molecules from K shell shape resonances Sette, F.; Stöhr, J.; Hitchcock, A. P. The Journal of Chemical Physics, Vol. 81, Issue 11 https://doi.org/10.1063/1.447528	journal	December 1984
Die Kristallstruktur von Imidazol, C ₃ N ₂ H ₄ , bei Zimmertemperatur Will, Georg Zeitschrift für Kristallographie, Vol. 129, Issue 1-4 https://doi.org/10.1524/zkri.1969.129.1-4.211	journal	May 1969
Prenucleation clusters and non-classical nucleation Gebauer, Denis; Cölfen, Helmut Nano Today, Vol. 6, Issue 6 https://doi.org/10.1016/j.nantod.2011.10.005	journal	December 2011
Self-association of imidazole and its methyl derivatives in aqueous solution. A study by ultraviolet spectroscopy Peral, F.; Gallego, E. Journal of Molecular Structure, Vol. 415, Issue 1-2 https://doi.org/10.1016/S0022-2860(97)00075-6	journal	August 1997
X-ray Absorption Spectroscopy Study of the Hydrogen Bond Network in the Bulk Water of Aqueous Solutions Näslund, Lars-Åke; Edwards, David C.; Wernet, Philippe The Journal of Physical Chemistry A, Vol. 109, Issue 27 https://doi.org/10.1021/jp050413s	journal	July 2005
Identification of Protonation State by XPS, Solid-State NMR, and DFT: Characterization of the Nature of a New Theophylline Complex by Experimental and Computational Methods Stevens, Joanna S.; Byard, Stephen J.; Muryn, Christopher A. The Journal of Physical Chemistry B, Vol. 114, Issue 44 https://doi.org/10.1021/jp106465u	journal	November 2010
Water ordering around methane during hydrate formation Koh, Carolyn A.; Wisbey, Robert P.; Wu, Xiaoping The Journal of Chemical Physics, Vol. 113, Issue 15 https://doi.org/10.1063/1.1288818	journal	October 2000
The Electronic Structure and Adsorption Geometry of l -Histidine on Cu(110) Feyer, Vitaliy; Plekan, Oksana; Skála, Tomáš The Journal of Physical Chemistry B, Vol. 112, Issue 43 https://doi.org/10.1021/jp805671h	journal	October 2008
A new imidazolylquinoline for organic thin film transistor Chen, Tsun-Ren; Yeh, Anchi; Chen, Jhy-Der Tetrahedron Letters, Vol. 46, Issue 9 https://doi.org/10.1016/j.tetlet.2004.12.139	journal	February 2005
Proton Transfer, Hydrogen Bonding, and Disorder: Nitrogen Near-Edge X-ray Absorption Fine Structure and X-ray Photoelectron Spectroscopy of Bipyridine–Acid Salts and Co-crystals Stevens, Joanna S.; Newton, Lauren K.; Jaye, Cherno Crystal Growth & Design, Vol. 15, Issue 4 https://doi.org/10.1021/cg5018278	journal	March 2015
Site-specific electronic structure of imidazole and imidazolium in aqueous solutions Meyer, F.; Blum, M.; Benkert, A. Physical Chemistry Chemical Physics, Vol. 20, Issue 12 https://doi.org/10.1039/C7CP07885D	journal	January 2018
Mode Recognition in UV Resonance Raman Spectra of Imidazole: Histidine Monitoring in Proteins Balakrishnan, Gurusamy; Jarzecki, Andrzej A.; Wu, Qiang The Journal of Physical Chemistry B, Vol. 116, Issue 31 https://doi.org/10.1021/jp305083t	journal	July 2012
Investigation of volatile liquid surfaces by synchrotron x-ray spectroscopy of liquid microjets Wilson, Kevin R.; Rude, Bruce S.; Smith, Jared Review of Scientific Instruments, Vol. 75, Issue 3 https://doi.org/10.1063/1.1645656	journal	March 2004
The nucleation of inosine: the impact of solution chemistry on the appearance of polymorphic and hydrated crystal forms Chiarella, Renato A.; Gillon, Amy L.; Burton, Rebecca C. Faraday Discussions, Vol. 136 https://doi.org/10.1039/b616164m	journal	January 2007
Solution crystallisation via a submerged liquid–liquid phase boundary: oiling out Bonnett, P. E.; Carpenter, K. J.; Dawson, S. Chemical Communications, Issue 6 https://doi.org/10.1039/b212062c	journal	February 2003
Photoemission from Liquid Aqueous Solutions Winter, Bernd; Faubel, Manfred Chemical Reviews, Vol. 106, Issue 4 https://doi.org/10.1021/cr040381p	journal	April 2006
Solvent structure and perturbations in solutions of chemical and biological importance Finney, J. L.; Soper, A. K. Chemical Society Reviews, Vol. 23, Issue 1 https://doi.org/10.1039/cs9942300001	journal	January 1994
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Uncovering Molecular Processes in Crystal Nucleation and Growth by Using Molecular Simulation Anwar, Jamshed; Zahn, Dirk Angewandte Chemie International Edition, Vol. 50, Issue 9 https://doi.org/10.1002/anie.201000463	journal	January 2011
Crystal nucleation in the presence of a metastable critical point Talanquer, V.; Oxtoby, David W. The Journal of Chemical Physics, Vol. 109, Issue 1 https://doi.org/10.1063/1.476554	journal	July 1998
Quantitative analysis of complex amino acids and RGD peptides by X-ray photoelectron spectroscopy (XPS): Quantitative XPS analysis of amino acids and RGD peptides Stevens, Joanna S.; de Luca, Alba C.; Pelendritis, Michalis Surface and Interface Analysis, Vol. 45, Issue 8 https://doi.org/10.1002/sia.5261	journal	April 2013
A molecular beam study of the evaporation of water from a liquid jet Faubel, M.; Schlemmer, S.; Toennies, J. P. Zeitschrift f�r Physik D Atoms, Molecules and Clusters, Vol. 10, Issue 2-3 https://doi.org/10.1007/BF01384861	journal	June 1988
X-ray excited optical luminescence (XEOL) detection of x-ray absorption fine structure (XAFS) Soderholm, L.; Liu, G. K.; Antonio, Mark R. The Journal of Chemical Physics, Vol. 109, Issue 16 https://doi.org/10.1063/1.477320	journal	October 1998
Enhancement of Protein Crystal Nucleation by Critical Density Fluctuations Wolde, Pieter Rein ten; Frenkel, Daan Science, Vol. 277, Issue 5334, p. 1975-1978 https://doi.org/10.1126/science.277.5334.1975	journal	September 1997
X-ray Spectroscopy of Liquid Water Microjets Wilson, Kevin R.; Rude, Bruce S.; Catalano, Tony The Journal of Physical Chemistry B, Vol. 105, Issue 17 https://doi.org/10.1021/jp010132u	journal	May 2001
The crystal structure of imidazole at –150°C Martinez-Carrera, S. Acta Crystallographica, Vol. 20, Issue 6 https://doi.org/10.1107/S0365110X66001853	journal	November 1966
A 1H NMR study of crystal nucleation in solution Spitaleri, Andrea; Hunter, Christopher A.; McCabe, James F. CrystEngComm, Vol. 6, Issue 80 https://doi.org/10.1039/b407163h	journal	January 2004
Universal Signature of Hydrogen Bonding in the Oxygen K -Edge Spectrum of Alcohols Pylkkänen, T.; Lehtola, J.; Hakala, M. The Journal of Physical Chemistry B, Vol. 114, Issue 41 https://doi.org/10.1021/jp106479a	journal	October 2010
Isotope effects in liquid water probed by x-ray Raman spectroscopy Bergmann, U.; Nordlund, D.; Wernet, Ph. Physical Review B, Vol. 76, Issue 2 https://doi.org/10.1103/PhysRevB.76.024202	journal	July 2007
Minimally augmented Karlsruhe basis sets Zheng, Jingjing; Xu, Xuefei; Truhlar, Donald G. Theoretical Chemistry Accounts, Vol. 128, Issue 3 https://doi.org/10.1007/s00214-010-0846-z	journal	December 2010
Ionization of Imidazole in the Gas Phase, Microhydrated Environments, and in Aqueous Solution Jagoda-Cwiklik, Barbara; Slavíček, Petr; Cwiklik, Lukasz The Journal of Physical Chemistry A, Vol. 112, Issue 16 https://doi.org/10.1021/jp711476g	journal	April 2008
Nucleation Vekilov, Peter G. Crystal Growth & Design, Vol. 10, Issue 12 https://doi.org/10.1021/cg1011633	journal	December 2010
Using a novel plug flow reactor for the in situ, simultaneous, monitoring of SAXS and WAXD during crystallisation from solution Alison, Harvey G.; Davey, Roger J.; Garside, John Physical Chemistry Chemical Physics, Vol. 5, Issue 22 https://doi.org/10.1039/b309309c	journal	January 2003
The crystal structure of imidazole by neutron diffraction at 20°C and –150°C Craven, B. M.; McMullan, R. K.; Bell, J. D. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 33, Issue 8 https://doi.org/10.1107/S0567740877008954	journal	August 1977
Experimental studies of the core excitation of imidazole, 4,5-dicyanoimidazole, and s-triazine Apen, Elizabeth; Hitchcock, Adam P.; Gland, John L. The Journal of Physical Chemistry, Vol. 97, Issue 26 https://doi.org/10.1021/j100128a019	journal	July 1993
Chemical Speciation and Bond Lengths of Organic Solutes by Core-Level Spectroscopy: pH and Solvent Influence on p -Aminobenzoic Acid Stevens, Joanna S.; Gainar, Adrian; Suljoti, Edlira Chemistry - A European Journal, Vol. 21, Issue 19 https://doi.org/10.1002/chem.201405635	journal	March 2015
Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model Barone, Vincenzo; Cossi, Maurizio The Journal of Physical Chemistry A, Vol. 102, Issue 11 https://doi.org/10.1021/jp9716997	journal	March 1998
Nucleation of First-Order Phase Transitions Oxtoby, David W. Accounts of Chemical Research, Vol. 31, Issue 2 https://doi.org/10.1021/ar9702278	journal	February 1998
Adsorption of Histidine and Histidine-Containing Peptides on Au(111) Feyer, Vitaliy; Plekan, Oksana; Tsud, Nataliya Langmuir, Vol. 26, Issue 11 https://doi.org/10.1021/la904684e	journal	June 2010
Aqueous Imidazole Solutions: A Structural Perspective from Simulations with High-Rank Electrostatic Multipole Moments Liem, Steven Y.; Shaik, Majeed S.; Popelier, Paul L. A. The Journal of Physical Chemistry B, Vol. 115, Issue 39 https://doi.org/10.1021/jp2053234	journal	October 2011
Prediction of molecular properties and molecular spectroscopy with density functional theory: From fundamental theory to exchange-coupling Neese, Frank Coordination Chemistry Reviews, Vol. 253, Issue 5-6 https://doi.org/10.1016/j.ccr.2008.05.014	journal	March 2009
Nucleation of Organic Crystals-A Molecular Perspective Davey, Roger J.; Schroeder, Sven L. M.; ter Horst, Joop H. Angewandte Chemie International Edition, Vol. 52, Issue 8 https://doi.org/10.1002/anie.201204824	journal	January 2013
Bonding of Histidine to Cerium Oxide Tsud, Nataliya; Acres, Robert G.; Iakhnenko, Marianna The Journal of Physical Chemistry B, Vol. 117, Issue 31 https://doi.org/10.1021/jp404385h	journal	July 2013
Influence of TMAO and urea on the structure of water studied by inelastic X-ray scattering Sahle, Christoph J.; Schroer, Martin A.; Juurinen, Iina Physical Chemistry Chemical Physics, Vol. 18, Issue 24 https://doi.org/10.1039/C6CP01922F	journal	January 2016
Efficient, approximate and parallel Hartree–Fock and hybrid DFT calculations. A ‘chain-of-spheres’ algorithm for the Hartree–Fock exchange Neese, Frank; Wennmohs, Frank; Hansen, Andreas Chemical Physics, Vol. 356, Issue 1-3 https://doi.org/10.1016/j.chemphys.2008.10.036	journal	February 2009
Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F. The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627 https://doi.org/10.1021/j100096a001	journal	November 1994
Concerning the Relationship between Structural and Growth Synthons in Crystal Nucleation: Solution and Crystal Chemistry of Carboxylic Acids As Revealed through IR Spectroscopy Davey, R. J.; Dent, G.; Mughal, R. K. Crystal Growth & Design, Vol. 6, Issue 8 https://doi.org/10.1021/cg060058a	journal	August 2006
X-ray Absorption Spectroscopy Measurements of Liquid Water Näslund, L. -Å.; Lüning, J.; Ufuktepe, Y. The Journal of Physical Chemistry B, Vol. 109, Issue 28 https://doi.org/10.1021/jp052046q	journal	July 2005
X-ray Raman spectroscopy at the oxygen K edge of water and ice: Implications on local structure models Bergmann, U.; Wernet, Ph.; Glatzel, P. Physical Review B, Vol. 66, Issue 9 https://doi.org/10.1103/PhysRevB.66.092107	journal	September 2002
Multielement spectrometer for efficient measurement of the momentum transfer dependence of inelastic x-ray scattering Fister, T. T.; Seidler, G. T.; Wharton, L. Review of Scientific Instruments, Vol. 77, Issue 6 https://doi.org/10.1063/1.2204581	journal	June 2006
Simulation of liquid imidazole using a high-rank quantum topological electrostatic potential Shaik, Majeed S.; Liem, Steven Y.; Yuan, Yongna Physical Chemistry Chemical Physics, Vol. 12, Issue 45 https://doi.org/10.1039/c0cp00417k	journal	January 2010
Fityk : a general-purpose peak fitting program Wojdyr, Marcin Journal of Applied Crystallography, Vol. 43, Issue 5 https://doi.org/10.1107/S0021889810030499	journal	September 2010
A miniature closed-circle flow cell for high photon flux X-ray scattering experiments Sahle, Ch. J.; Henriquet, C.; Schroer, M. A. Journal of Synchrotron Radiation, Vol. 22, Issue 6 https://doi.org/10.1107/S1600577515016331	journal	September 2015
Saturation Behavior in X-ray Raman Scattering Spectra of Aqueous LiCl Juurinen, Iina; Pylkkänen, Tuomas; Ruotsalainen, Kari O. The Journal of Physical Chemistry B, Vol. 117, Issue 51 https://doi.org/10.1021/jp409528r	journal	December 2013