Conformational flexibility and hydrogen‐bonding patterns of the neotame molecule in its various solid forms

Dong, Zedong; Munson, Eric J.; Schroeder, Steve A.; Prakash, Indra; Grant, David J.W.

doi:10.1002/jps.10192

Cited by 2 publications

(1 citation statement)

References 27 publications

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“…Neotame20 was chosen because it has multiple polymorphic forms and can readily be prepared in the amorphous state 21. The focus of this research is the absolute quantitation of three different forms of anhydrous neotame: crystalline polymorphs labeled Form A19 and Form G19,35,36 as found in the literature; and amorphous neotame. Quantitation data was obtained using high‐resolution SSNMR spectroscopy with magic‐angle spinning (MAS) and CP.…”

Section: Introductionmentioning

confidence: 99%

Quantitation of crystalline and amorphous forms of anhydrous neotame using 13C CPMAS NMR spectroscopy

Offerdahl

Salsbury

Dong

et al. 2005

Journal of Pharmaceutical Sciences

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Section: Introductionmentioning

confidence: 99%

Quantitation of crystalline and amorphous forms of anhydrous neotame using 13C CPMAS NMR spectroscopy

Offerdahl

Salsbury

Dong

et al. 2005

Journal of Pharmaceutical Sciences

Self Cite

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Crystallization Pathways and Kinetics of Carbamazepine–Nicotinamide Cocrystals from the Amorphous State by In Situ Thermomicroscopy, Spectroscopy, and Calorimetry Studies

Seefeldt

Miller

Alvarez‐Núñez

et al. 2007

Journal of Pharmaceutical Sciences

153

127

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The work presented here was motivated by the premise that the amorphous state serves as a medium to study cocrystal formation. The molecular mobility inherent to amorphous phases can lead to molecular associations between different components such that a single crystalline phase of multiple components or cocrystal is formed. Cocrystallization pathways and kinetics were investigated from amorphous equimolar phases of carbamazepine and nicotinamide using hot-stage polarized microscopy (HSPM), hot-stage Raman microscopy (HSRM), differential scanning calorimetry (DSC), and X-ray powder diffraction (XRPD). Nonisothermal studies revealed that amorphous phases generate cocrystals and that thermal history affects crystallization pathways in significant ways. Two different pathways to cocrystal formation from the amorphous phase were identified: (1) at low heating rates (3 degrees C/min) a metastable cocrystalline phase initially nucleates and transforms to the more stable cocrystalline phase of CBZ-NCT, and (2) at higher heating rates (10 degrees C/min) individual components crystallize, then melt and the stable cocrystalline phase nucleates and grows from the melt. Isothermal studies above the T(g) of the amorphous equimolar phase also confirm the nucleation of a metastable cocrystalline phase from the amorphous state followed by a solid phase mediated transformation to the stable cocrystalline phase. Cocrystallization kinetics were measured by image analysis and by thermal analysis from small samples and are described by the Avrami-Erofeev model. These findings have important implications for the use of amorphous phases in the discovery of cocrystals and to determine the propensity of cocrystallization from process-induced amorphization.

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Conformational flexibility and hydrogen‐bonding patterns of the neotame molecule in its various solid forms

Cited by 2 publications

References 27 publications

Quantitation of crystalline and amorphous forms of anhydrous neotame using 13C CPMAS NMR spectroscopy

Quantitation of crystalline and amorphous forms of anhydrous neotame using 13C CPMAS NMR spectroscopy

Crystallization Pathways and Kinetics of Carbamazepine–Nicotinamide Cocrystals from the Amorphous State by In Situ Thermomicroscopy, Spectroscopy, and Calorimetry Studies

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