Influence of solvent on crystal nucleation of benzocaine

Cheuk, Dominic; Żegliński, Jacek; Krishnaraj, Renuka; Rasmuson, Åke C.

doi:10.1039/d0ce01306d

Cited by 6 publications

(8 citation statements)

References 49 publications

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“…Finally, we screened the sources of palladium and studied five different palladium catalysts. Therefore, we found that [PdCl (C 3 H 5 )] 2 is the best palladium source (Table 1, entry [17][18][19][20][21].…”

Section: Resultsmentioning

confidence: 99%

Palladium Catalyzed Carbonyl Amination of Fluorinated Olefins for Synthesis of α‐CF₃‐Acrylamides

Li,

Jing,

Shi

et al. 2024

Eur J Org Chem

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Acrylamides are a class of important organic compounds that play key roles in biomedical chemistry, materials science, life science, and other fields. Due to the strong electron‐withdrawing effect of trifluoromethyl, the synthesis of trifluoromethylated acrylamides, especially those containing double bonds, has long been a challenge. Here, we report an example of the formation of trifluoromethyl acrylamides through palladium catalyzedcarbonylation of fluorinated olefins. By optimizing the reaction conditions, we can obtain different amide compounds, including alkyl acrylamides. aromatic acrylamides and heterocyclic acrylamides. This method has good substrate adaptability and functional group tolerance,so it is expected to be used in the synthesis of key amides in the fields of medicine and other fields.

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Section: Resultsmentioning

confidence: 99%

Palladium Catalyzed Carbonyl Amination of Fluorinated Olefins for Synthesis of α‐CF₃‐Acrylamides

Li,

Jing,

Shi

et al. 2024

Eur J Org Chem

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“…Furthermore, no infrared peak shift was observed during the whole process, indicating that the solute molecules may exist stably in a certain mode in solution. The −CO stretch mode is a sensitive probe to distinguish aggregation modes due to their differences in hydrogen bond strength. − It can be seen from Figure a,b that the stretching vibration peaks of −CO in ethanol and the ethanol/ n -heptane system are both located at 1705 cm –1 , indicating that the chlorpropamide molecules may exist in the form of solvated monomers. Furthermore, it is worth noting that, in ethanol/ n -heptane, apart from the main peak at 1705 cm –1 , the shoulder peak at 1725 cm –1 may represent the presence of weaker interaction solvent–solute clusters.…”

Section: Resultsmentioning

confidence: 99%

Selective Nucleation of Polymorphs Induced by Multiple Conformations and Self-Association

Liu

Wang

Zhao

et al. 2022

Crystal Growth & Design

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In an attempt to understand the relationship between solution chemistry and polymorphic nucleation, the flexible molecule chlorpropamide is used as a model compound to study its cooling crystallization behavior in four solvent systems. Online ATR-FTIR spectra proved the existence of dimers and solvated monomers in the solution. 2D nuclear overhauser effect spectroscopy and molecular dynamics simulations further revealed the molecular preassembled species in the solution. The results show that, in ethanol, ethanol/n-heptane, and ethyl acetate/n-heptane solvents, the solute molecules exist in the form of solvated monomers in multiple conformations. The stable formation of metastable form γ in ethyl acetate/n-heptane shows that, compared to conformational flexibility, the desolvation process plays a crucial role in overall self-assembly during the nucleation process. While in ethyl acetate, the solute molecules mainly exist as dimers and the rearrangement of the "wrong conformation" dimers becomes a key step to the nucleation rate and leads to the formation of stable form α. As a result, the self-association mode and conformational distribution of chlorpropamide in the solution work together to affect the nucleation process and polymorphic outcome.

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“…As a result, there is significant research interest in establishing a relationship between nucleation pathway and solution structure, with the observed nucleation induction time, in order to improve process understanding and control over crystal nucleation from solution. Previous literature has reported that solvent–solute interactions (i.e., the overall solvent–solute interaction or the specific site's solvent–solute interaction) was correlated with the impeded nucleation salicylic acid, 15 isonicotinamide, 21 risperidone, 22 etoricoxib, 23 p ‐nitrobenzoic acid, 24 and benzocaine 25 . In these cases, stronger solute–solvent interaction resulted in higher energy barrier for nucleation resulting in reduced rates of nucleation or extended induction times.…”

Section: Introductionmentioning

confidence: 99%

“…Previous literature has reported that solvent-solute interactions (i.e., the overall solvent-solute interaction or the specific site's solvent-solute interaction) was correlated with the impeded nucleation salicylic acid, 15 isonicotinamide, 21 risperidone, 22 etoricoxib, 23 p-nitrobenzoic acid, 24 and benzocaine. 25 In these cases, stronger solute-solvent interaction resulted in higher energy barrier for nucleation resulting in reduced rates of nucleation or extended induction times.…”

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confidence: 99%

The role of solute conformation, solvent–solute and solute–solute interactions in crystal nucleation

Wang

Huang

et al. 2023

AIChE Journal

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The induction time for nucleation can differ based on the solutions used to conduct a crystallization, which can in turn impact the efficiency and economics of a crystallization process, the crystal size distribution, the morphology and ultimately functionality of the final product. Establishing a link between the nucleation pathway/solution structure and nucleation induction time is essential to achieve improved comprehension of the process of crystal nucleation from solution. In this study, the role of solute conformation, solvent-solute interaction, and solute-solute interaction in nucleation was examined using tolbutamide as a model compound in toluene and toluenealcohol solutions. Through a combination of induction time experiments, attenuated total reflection Fourier transformed infrared spectroscopy, nuclear magnetic resonance spectroscopy, molecular dynamics simulations, and quantum chemical calculations, it was found that not only solvent-solute interactions but also solute-solute interactions and structural similarities between molecular self-assemblies in the solution and synthons in the crystal structure, can significantly influence the nucleation induction time.

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Influence of solvent on crystal nucleation of benzocaine

Abstract: The influence of the solvent in nucleation of benzocaine FII was explored by measuring nucleation induction times, probing solvent–solute interactions with spectroscopy and modelling the strength of solvent–solute intermolecular interactions using DFT.

Cited by 6 publications

References 49 publications

Palladium Catalyzed Carbonyl Amination of Fluorinated Olefins for Synthesis of α‐CF₃‐Acrylamides

Palladium Catalyzed Carbonyl Amination of Fluorinated Olefins for Synthesis of α‐CF₃‐Acrylamides

Selective Nucleation of Polymorphs Induced by Multiple Conformations and Self-Association

The role of solute conformation, solvent–solute and solute–solute interactions in crystal nucleation

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Influence of solvent on crystal nucleation of benzocaine

Abstract: The influence of the solvent in nucleation of benzocaine FII was explored by measuring nucleation induction times, probing solvent–solute interactions with spectroscopy and modelling the strength of solvent–solute intermolecular interactions using DFT.

Cited by 6 publications

References 49 publications

Palladium Catalyzed Carbonyl Amination of Fluorinated Olefins for Synthesis of α‐CF3‐Acrylamides

Palladium Catalyzed Carbonyl Amination of Fluorinated Olefins for Synthesis of α‐CF3‐Acrylamides

Selective Nucleation of Polymorphs Induced by Multiple Conformations and Self-Association

The role of solute conformation, solvent–solute and solute–solute interactions in crystal nucleation

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Palladium Catalyzed Carbonyl Amination of Fluorinated Olefins for Synthesis of α‐CF₃‐Acrylamides

Palladium Catalyzed Carbonyl Amination of Fluorinated Olefins for Synthesis of α‐CF₃‐Acrylamides