Structural evidence of polymorphism and conformational isomorphism of a somewhat flexible molecule: m-anisic acid

Silva, Pedro S. Pereira; Castro, Ricardo A. E.; Melro, Elodie; Silva, Manuela Ramos; Maria, Teresa M. R.; Canotilho, João; Eusébio, M. Ermelinda S.

doi:10.1007/s10973-014-4289-y

Cited by 14 publications

(4 citation statements)

References 39 publications

(34 reference statements)

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“…142°C [10]. 1 The products were re-crystalized or distilled under reduced pressure. No impurities (greater than 0.001 mass fractions) could be detected in samples used for the before the thermochemical measurements.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…They are used as flavoring substances and preservatives of fragrance in cosmetic formulations [1]. As some of them are natural products, they are good candidates for pharmaceutical co-crystals [1]. Several alkoxybenzoic acids and their derivatives reveal biological activity as inhibitors of phosphodiesterase [2].…”

Section: Introductionmentioning

confidence: 99%

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Thermodynamic properties of isomeric iso-butoxybenzoic acids: Experimental and theoretical study

et al. 2015

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Thermodynamic properties of isomeric iso-butoxybenzoic acids: Experimental and theoretical study

et al. 2015

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“…Regarding research on conformationally flexible molecules, Garcia-Garibay et al evaluated the isomorphism of molecular rotors and showed that isomorphism arises from the closely isosteric relation that exists between hydrogen and fluorine atoms. Castro et al . applied a multidisciplinary approach and showed that the molecular flexibility of m -anisic acid results in the presence of two conformers in the unit cell.…”

Section: Introductionmentioning

confidence: 99%

Persistence of N—H···O═C Interactions in the Crystallization Mechanisms of Trisubstituted Bis-Ureas with Bulky Substituents

Lopes

Orlando

Simões

et al. 2021

Crystal Growth & Design

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Bis-ureas are generally associated with strongly bifurcated hydrogen bonds (NH···OC interactions). For this reason, a series of trisubstituted bis-ureas (TBU) with bulk substituents were designed and used as a study model to gain a better understanding of the persistence of NH···OC interactions as driving interactions of the crystallization process. The TBU molecules possess different substituents (isopropyl, benzyl, and 4-nitro-benzyl) and variations in the methylene spacer. The TBU self-assembly, through crystallization mechanism proposals, is discussed related to the role of intermolecular interactions that drive and participate in the crystallization process. The intermolecular interactions present in the proposed first nuclei of crystallization were studied by concentration-dependent 1H NMR experiments and QTAIM analysis. Our findings showed that even with bulky substituents, the NH···OC interactions in most compounds played an important role in stabilizing the first nuclei formed during the crystallization process. However, in one case the molecular topology prevented the formation of NH···OC as the driving interaction in the first crystallization nuclei. In this case, the crystallization was mainly governed by a set of “weaker” interactions, showing that a subtle molecular change in the methylene spacer favored H···H interactions over directional N–H···O interactions. For some of the compounds studied, we propose both when the symmetry-independent molecules observed in the crystal lattice could be formed and when the water molecules are probably trapped during the crystallization to form the hydrate crystalline phases. This study contributes to the better understanding of issues related to modulating NH···OC hydrogen bonds using bulky substituents in the self-assembly of flexible TBU molecules.

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[2](1,3)Adamantano[2](2,7)pyrenophane: A Hydrocarbon with a Large Dipole Moment

et al. 2016

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The fusion of the sp 3 -hybridized parent diamondoid adamantane with the sp 2 -hybridized pyrene results in ahybrid structure with av ery large dipole moment which arises from bending the pyrene moiety.P resented herein is the synthesis, study of the electronic and optical properties,a sw ell as the dynamic behavior of this new hydrocarbon.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under http://dx.

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Structural evidence of polymorphism and conformational isomorphism of a somewhat flexible molecule: m-anisic acid

Cited by 14 publications

References 39 publications

Thermodynamic properties of isomeric iso-butoxybenzoic acids: Experimental and theoretical study

Thermodynamic properties of isomeric iso-butoxybenzoic acids: Experimental and theoretical study

Persistence of N—H···O═C Interactions in the Crystallization Mechanisms of Trisubstituted Bis-Ureas with Bulky Substituents

[2](1,3)Adamantano[2](2,7)pyrenophane: A Hydrocarbon with a Large Dipole Moment

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