Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures

Raffo, Pablo Alejandro; Rossi, Leonardo; Alborés, Pablo; Baggio, Ricardo; Cukiernik, Fabio Daniel

doi:10.1016/j.molstruc.2014.04.003

Cited by 13 publications

(10 citation statements)

References 30 publications

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“…Crystalline structures of o-anisic acid [9] and of p-anisic acid [10] are already available in literature. Very recent data, however, with a CCDC number superior to ours, could be found for m-anisic acid [11] but without any reference to polymorphism.…”

Section: Introductioncontrasting

confidence: 64%

See 1 more Smart Citation

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

Silva

Castro

Melro

et al. 2014

J Therm Anal Calorim

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m-Anisic acid is generally recognized as a safe (GRAS) flavouring substance. Its GRAS status and the functional groups present in the molecule make it an interesting candidate for pharmaceutical co-crystallization studies. The knowledge of m-anisic acid crystalline structure/ polymorphic behaviour is important information for its applications. In this work, a crystalline structure of m-anisic acid form I, T fus = 105°C, was solved by X-ray diffraction: monoclinic, space group P2 1 /n, with a = 13.8075 (5) Å , b = 5.0221(2) Å , c = 21.4455(8) Å , b = 99.325(3)°, Mr = 331.37, V = 1467.44(10) Å 3 , Z = 8 and R = 0.0395 (CCDC No. 985352). A recent paper by Raffo et al. (J Mol Struct 1070:86-93, 2014) (CCDC No. 985637) also resolved the structure, and within experimental error, the two structures are equal. The molecular flexibility of m-anisic acid results in the presence of two conformers in the unit cell, a rare case of conformational isomorphism. These two conformers were found by ab initio calculations to differ in energy by 4.9 kJ mol -1 . Solid samples were generated by crystallization from solutions and by melt cooling. Using a multidisciplinary approach involving thermal analysis (DSC, PLTM), infrared spectroscopy and X-ray powder diffraction, a new monotropic solid form II, T fus = 94°C, was identified and characterized. Polymorph II slowly transforms into polymorph I at room temperature.

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Section: Introductioncontrasting

confidence: 64%

“…During the preparation of our manuscript, another group determined almost simultaneously (CCDC No. 985637) the crystal structure of polymorph I [11]. Within experimental error, the two structures are equal.…”

Section: Resultsmentioning

confidence: 92%

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

Silva

Castro

Melro

et al. 2014

J Therm Anal Calorim

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“…Ground state (μ g ) and excited state (μ e ) dipole moments are determined from the slopes (m (1) ) and (m (2) ) of the Bilot-Kawski correlations by applying Eqs. (7) and (8) 16) and (24). All of the results are presented in Table 5.…”

Section: Experimentally and Theoretically Estimation Of Ground And Exmentioning

confidence: 94%

“…Additionally, alkyl chain length is a very important parameter which influences the properties of mesogen molecules [19,20]. Depending on the detailed literature investigation of alkoxybenzoic acid and 4-alkoxybenzoic acid liquid crystals, it seems that most of the studies are focused on liquid crystal properties and crystal structure [21][22][23][24][25]15], and thermodynamic and spectroscopic properties [26][27][28][29][30][31]17,18].…”

Section: Introductionmentioning

confidence: 99%

Solvatochromic fluorescence of 4-alkoxybenzoic acid liquid crystals: Ground and excited state dipole moments of monomer and dimer structures determined by solvatochromic shift methods

Sıdır

2015

Journal of Molecular Liquids

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“…These systems also attracted a lot of attention due to the pieces of evidence of proton transfer and proton tunneling . On the other hand, benzene and its derivatives undergo stacking interactions, which are particularly relevant in living organisms, but are also significant for crystal packing . We have thus chosen the BA as the smallest representative of aromatic carboxylic acids for theoretical analysis of noncovalent interactions.…”

Section: Introductionmentioning

confidence: 99%

Theoretical scrutinization of nine benzoic acid dimers: Stability and energy decomposition analysis

Petrović

Milovanovic

Etinski

et al. 2019

Int J of Quantum Chemistry

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Aromatic carboxylic acids are able to form diverse dimers and multimers due to their hydrogen bond donor and acceptor cites, as well as the aromatic rings. In this work, we examine nine benzoic acid dimers stabilized by hydrogen bonding and stacking interactions. Interacting quantum atoms methodology revealed that dominant attractive interactions in all of them, including hydrogen bonded systems, are due to exchange-correlation. Coulomb interactions are significant only in the most stable dimer with a double hydrogen bond, although the corresponding energy term is almost two times lower compared to the nonclassical one. Since interacting quantum atoms approach treats monomers binding by considering electronic energy only, in order to examine dissociation kinetics we performed density functional theory-based molecular dynamics simulations of selected stacked dimers: in 40% of the studied systems at 300 K thermal energy was sufficient to overpower barrier for dissociation within 1 ps, which resulted in the separation of the monomers, whereas 20% of them remained in the stacked position even after 5 ps. These results highlight the importance of noncovalent interactions, particularly weak stacking interactions, on the structure and dynamics of carboxylic acids and their derivatives.benzoic acid dimer, density functional theory-based molecular dynamics, interacting quantum fragments, noncovalent interactions

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Alkoxy-benzoic acids: Some lacking structures and rationalization of the molecular features governing their crystalline architectures

Cited by 13 publications

References 30 publications

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

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

Solvatochromic fluorescence of 4-alkoxybenzoic acid liquid crystals: Ground and excited state dipole moments of monomer and dimer structures determined by solvatochromic shift methods

Theoretical scrutinization of nine benzoic acid dimers: Stability and energy decomposition analysis

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