Structural basis for the transformation pathways of the sodium naproxen anhydrate-hydrate system

Research output: Contribution to journalJournal article

Standard

Structural basis for the transformation pathways of the sodium naproxen anhydrate-hydrate system. / Bond, Andrew; Cornett, Claus; Larsen, Flemming Hofmann; Qu, Haiyan; Raijada, Dharaben Kaushikkumar; Rantanen, Jukka.

In: IUCrJ, Vol. 1, No. 5, 2014, p. 328-337.

Research output: Contribution to journalJournal article

Harvard

Bond, A, Cornett, C, Larsen, FH, Qu, H, Raijada, DK & Rantanen, J 2014, 'Structural basis for the transformation pathways of the sodium naproxen anhydrate-hydrate system', IUCrJ, vol. 1, no. 5, pp. 328-337. https://doi.org/10.1107/S2052252514015450

APA

Bond, A., Cornett, C., Larsen, F. H., Qu, H., Raijada, D. K., & Rantanen, J. (2014). Structural basis for the transformation pathways of the sodium naproxen anhydrate-hydrate system. IUCrJ, 1(5), 328-337. https://doi.org/10.1107/S2052252514015450

Vancouver

Bond A, Cornett C, Larsen FH, Qu H, Raijada DK, Rantanen J. Structural basis for the transformation pathways of the sodium naproxen anhydrate-hydrate system. IUCrJ. 2014;1(5):328-337. https://doi.org/10.1107/S2052252514015450

Author

Bond, Andrew ; Cornett, Claus ; Larsen, Flemming Hofmann ; Qu, Haiyan ; Raijada, Dharaben Kaushikkumar ; Rantanen, Jukka. / Structural basis for the transformation pathways of the sodium naproxen anhydrate-hydrate system. In: IUCrJ. 2014 ; Vol. 1, No. 5. pp. 328-337.

Bibtex

@article{e135bb9e10d94308a9e072f679e707b6,
title = "Structural basis for the transformation pathways of the sodium naproxen anhydrate-hydrate system",
abstract = "Crystal structures are presented for two dihydrate polymorphs (DH-I and DH-II) of the non-steroidal anti-inflammatory drug sodium (S)-naproxen. The structure of DH-I is determined from twinned single crystals obtained by solution crystallization. DH-II is obtained by solid-state routes, and its structure is derived using powder X-ray diffraction, solid-state (13)C and (23)Na MAS NMR, and molecular modelling. The validity of both structures is supported by dispersion-corrected density functional theory (DFT-D) calculations. The structures of DH-I and DH-II, and in particular their relationships to the monohydrate (MH) and anhydrate (AH) structures, provide a basis to rationalize the observed transformation pathways in the sodium (S)-naproxen anhydrate-hydrate system. All structures contain Na(+)/carboxylate/H2O sections, alternating with sections containing the naproxen molecules. The structure of DH-I is essentially identical to MH in the naproxen region, containing face-to-face arrangements of the naphthalene rings, whereas the structure of DH-II is comparable to AH in the naproxen region, containing edge-to-face arrangements of the naphthalene rings. This structural similarity permits topotactic transformation between AH and DH-II, and between MH and DH-I, but requires re-organization of the naproxen molecules for transformation between any other pair of structures. The topotactic pathways dominate at room temperature or below, while the non-topotactic pathways become active at higher temperatures. Thermochemical data for the dehydration processes are rationalized in the light of this new structural information.",
author = "Andrew Bond and Claus Cornett and Larsen, {Flemming Hofmann} and Haiyan Qu and Raijada, {Dharaben Kaushikkumar} and Jukka Rantanen",
note = "OA",
year = "2014",
doi = "10.1107/S2052252514015450",
language = "English",
volume = "1",
pages = "328--337",
journal = "I U Cr J",
issn = "2052-2525",
publisher = "International Union of Crystallography",
number = "5",

}

RIS

TY - JOUR

T1 - Structural basis for the transformation pathways of the sodium naproxen anhydrate-hydrate system

AU - Bond, Andrew

AU - Cornett, Claus

AU - Larsen, Flemming Hofmann

AU - Qu, Haiyan

AU - Raijada, Dharaben Kaushikkumar

AU - Rantanen, Jukka

N1 - OA

PY - 2014

Y1 - 2014

N2 - Crystal structures are presented for two dihydrate polymorphs (DH-I and DH-II) of the non-steroidal anti-inflammatory drug sodium (S)-naproxen. The structure of DH-I is determined from twinned single crystals obtained by solution crystallization. DH-II is obtained by solid-state routes, and its structure is derived using powder X-ray diffraction, solid-state (13)C and (23)Na MAS NMR, and molecular modelling. The validity of both structures is supported by dispersion-corrected density functional theory (DFT-D) calculations. The structures of DH-I and DH-II, and in particular their relationships to the monohydrate (MH) and anhydrate (AH) structures, provide a basis to rationalize the observed transformation pathways in the sodium (S)-naproxen anhydrate-hydrate system. All structures contain Na(+)/carboxylate/H2O sections, alternating with sections containing the naproxen molecules. The structure of DH-I is essentially identical to MH in the naproxen region, containing face-to-face arrangements of the naphthalene rings, whereas the structure of DH-II is comparable to AH in the naproxen region, containing edge-to-face arrangements of the naphthalene rings. This structural similarity permits topotactic transformation between AH and DH-II, and between MH and DH-I, but requires re-organization of the naproxen molecules for transformation between any other pair of structures. The topotactic pathways dominate at room temperature or below, while the non-topotactic pathways become active at higher temperatures. Thermochemical data for the dehydration processes are rationalized in the light of this new structural information.

AB - Crystal structures are presented for two dihydrate polymorphs (DH-I and DH-II) of the non-steroidal anti-inflammatory drug sodium (S)-naproxen. The structure of DH-I is determined from twinned single crystals obtained by solution crystallization. DH-II is obtained by solid-state routes, and its structure is derived using powder X-ray diffraction, solid-state (13)C and (23)Na MAS NMR, and molecular modelling. The validity of both structures is supported by dispersion-corrected density functional theory (DFT-D) calculations. The structures of DH-I and DH-II, and in particular their relationships to the monohydrate (MH) and anhydrate (AH) structures, provide a basis to rationalize the observed transformation pathways in the sodium (S)-naproxen anhydrate-hydrate system. All structures contain Na(+)/carboxylate/H2O sections, alternating with sections containing the naproxen molecules. The structure of DH-I is essentially identical to MH in the naproxen region, containing face-to-face arrangements of the naphthalene rings, whereas the structure of DH-II is comparable to AH in the naproxen region, containing edge-to-face arrangements of the naphthalene rings. This structural similarity permits topotactic transformation between AH and DH-II, and between MH and DH-I, but requires re-organization of the naproxen molecules for transformation between any other pair of structures. The topotactic pathways dominate at room temperature or below, while the non-topotactic pathways become active at higher temperatures. Thermochemical data for the dehydration processes are rationalized in the light of this new structural information.

U2 - 10.1107/S2052252514015450

DO - 10.1107/S2052252514015450

M3 - Journal article

VL - 1

SP - 328

EP - 337

JO - I U Cr J

JF - I U Cr J

SN - 2052-2525

IS - 5

ER -

ID: 130757864