Physical transformations of the active pharmaceutical ingredient BN83495: enantiotropic and monotropic relationships. Access to several polymorphic forms by using various solvation–desolvation processes

Martins, Damien; Sanselme, Morgane; Houssin, O.; Dupray, Valérie; Petit, Marie‐Noëlle; Pasquier, Diego; Diolez, Christian; Coquerel, Gérard

doi:10.1039/c2ce06537a

Cited by 17 publications

(9 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The mechanism of crystal transformation due to desolvation has been suggested to occur via displacive motion 101−103 or a reconstructive phase transition. 104,105 Similar studies have used AFM to describe comparable solid-state transformations related to, for example, dehydration, 106 polymorphic transitions, 107,108 and amorphous crystallization. 109,110 However, the AFM results shown here are, to the best of our knowledge, the first to exhibit in situ recrystallization originating from internal desolvation.…”

Section: Discussionmentioning

confidence: 99%

Study of Physicochemical and Explosive Properties of a 2,4,6-Trinitrotoluene/Aniline Cocrystal Solvate

Fondren

Unruh

et al. 2019

Crystal Growth & Design

View full text Add to dashboard Cite

In the development of crystal engineering and supramolecular chemistry, cocrystallization has been used as a way to develop novel explosives with tailored properties. We present a novel cocrystal solvate composed of 2,4,6trinitrotoluene (TNT) and aniline that exhibits unique physicochemical and explosive properties. X-ray diffraction studies reveal the crystallographic structure to contain TNT and aniline in a 1:1 molecular ratio. The crystals themselves exhibit a vibrant, ruby red color that likely results due to a charge-transfer interaction between the overlapping π-orbitals of the aromatic rings. The most notable evidence for a chargetransfer complex is the appearance of a broad absorbance peak in the visible region which is not present in the spectrum of either pure component. Comparisons of the cocrystal solvate to that of pure TNT are conducted to determine thermodynamic and kinetic parameters using both experimental and theoretical techniques. The desolvation of aniline from the cocrystal solvate was also investigated using both in situ powder X-ray diffraction and atomic force microscopy measurements to monitor changes in the crystal structure and surface topography, respectively.

show abstract

Section: Discussionmentioning

confidence: 99%

Study of Physicochemical and Explosive Properties of a 2,4,6-Trinitrotoluene/Aniline Cocrystal Solvate

Fondren

Unruh

et al. 2019

Crystal Growth & Design

View full text Add to dashboard Cite

show abstract

“…A literature overview covering the two last decades (see e.g. refs − ) indicates however that such simple classification suffers insufficiencies, since the existence of complex behaviors cannot be readily addressed without extension or modification of the existing framework. Concepts such as cooperativity, packing frustration, concerted movements, microstructure and mosaicity, modulated structures, zip-like mechanisms, anomalous thermal expansion, lattice strains, internal molecular motions, mesoscopic effects, etc.…”

Section: Introductionmentioning

confidence: 99%

Mechanisms of Reversible Phase Transitions in Molecular Crystals: Case of Ciclopirox

et al. 2015

View full text Add to dashboard Cite

The detailed characterization of several subambient solid state transitions occurring in the pharmaceutical ingredient Ciclopirox between −20 °C and −85 °C was performed by using a combination of DSC, cold-stage optical microscopy, vibrational spectroscopies, solid state NMR at controlled temperature, structural analyses by single crystal X-ray diffraction, and temperature-resolved X-ray powder diffraction. The global analysis of the available data reveals that the mechanisms of these reversible transitions involve a subtle compromise between phenomena related to molecular disorder, cooperative release of strains induced by cooling, and structural reorganization associated with topotactic changes in crystal lattice and symmetry. However, no major change in the main features of crystal packings is observed during the successive single crystal-to-single crystal transitions, which highlights the difficulty to classify such transitions in the frame of conventional theoretical frameworks. The successive thermal events and related structural changes or relaxations can be seen as the consequences of a deconvolution phenomenon for the global phase transition between the dynamically disordered room temperature form (C2/c, Z = 8, Z′ = 1) and the ordered low-temperature form (P2 1 /c, Z = 48, Z′ = 12). In this respect, the intermediate form(s) can be seen as transient states of kinetic origin with a questionable genuine crystallographic relevance.

show abstract

“…The study of all the possible solvates that can be formed with an API is also important in the pharmaceutical industry. Indeed, solvates sometimes play a crucial role in which the solvent evaporation can generate new polymorphs which are only accessible via the preliminary formation of the solvates. , Moreover, different desolvation mechanisms are described in order to understand the formation of the desolvated phases, − and some examples can be found in the literature. − …”

Section: Introductionmentioning

confidence: 99%

Access to Several Polymorphic Forms of (±)-Modafinil by Using Various Solvation–Desolvation Processes

Mahieux

Sanselme

Coquerel

2015

Crystal Growth & Design

View full text Add to dashboard Cite

The solid state landscape of (±)-modafinil presents several polymorphic forms and solvates. Some of these polymorphic forms ((±)-Forms V and VI) can only be obtained by means of desolvation of solvates ((±)-modafinil chloroform solvate and acetonitrile solvate). Moreover, a new hydrate ((±)-modafinil monohydrate) is obtained from an original protocol which uses a physical mixture of both enantiomers rather than the racemic compound. All these solvates present an efflorescent behavior, and this study highlights the formation of various polymorphic forms from the same solvate according to the temperature of desolvation. Indeed, when the desolvation process is performed below or above the glass transition temperature (T g) of the anhydrous modafinil, the resulting nonsolvated phases differ.

show abstract

Physical transformations of the active pharmaceutical ingredient BN83495: enantiotropic and monotropic relationships. Access to several polymorphic forms by using various solvation–desolvation processes

Cited by 17 publications

References 22 publications

Study of Physicochemical and Explosive Properties of a 2,4,6-Trinitrotoluene/Aniline Cocrystal Solvate

Study of Physicochemical and Explosive Properties of a 2,4,6-Trinitrotoluene/Aniline Cocrystal Solvate

Mechanisms of Reversible Phase Transitions in Molecular Crystals: Case of Ciclopirox

Access to Several Polymorphic Forms of (±)-Modafinil by Using Various Solvation–Desolvation Processes

Contact Info

Product

Resources

About