The Crystal Structure of the More-soluble Mosher’s Salt

Ichikawa, Akio; Ono, Hiroshi; Mikata, Yuji

doi:10.1246/cl.161111

Cited by 2 publications

(7 citation statements)

References 27 publications

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“…This class of organic salts prefers the sup S association over the sup R association [10]. Figure 7 show the interatomic distances H11···C19 and H12···C18 (d L and d M , respectively) and the interatomic angles C11-H11···C19 and C12-H12···C18 in the close ion-pairs of salts 6-9.…”

Section: Saltmentioning

confidence: 98%

“…Considering the virtual chiral center of the carboxylate and methoxy groups of the (R)-MαNP anion and the phenyl and ammonium groups of the (R)-1-arylethylammonium cation, each of the supramolecular chirality in the close ion-pairs of salts 6-9 was assigned as sup S (Figures 2B and 3). This class of organic salts prefers the sup S association over the sup R association [10]. Considering the virtual chiral center of the carboxylate and methoxy groups of the (R)-MαNP anion and the phenyl and ammonium groups of the (R)-1-arylethylammonium cation, each of the supramolecular chirality in the close ion-pairs of salts 6-9 was assigned as sup S (Figures 2B and 3).…”

Section: Saltmentioning

confidence: 99%

“…Additionally, results have shown that intercolumnar aromatic C-H···π interactions [7][8][9] are more effective with the less-soluble salt 4. [6,10]. Assigned numbers indicate priority based on the Cahn-Ingold-Prelog rules.…”

Section: Introductionmentioning

confidence: 99%

“…In 2007, Müller et al reported that ca. 20% of all pharmaceuticals, and even more agrochemicals (up to 30%), carboxylate and methoxy groups of the (R)-MαNP anion and the phenyl and ammonium groups of the (R)-PEA cation, the supramolecular chirality of salt 4 was assigned as sup S ( Figure 2B) [10]. Salts 4 and 5 [(R)-1-(p-tolyl)ethylamine•(R)-1] yielded space groups P21 and C2, respectively [6,11].…”

Section: Introductionmentioning

confidence: 99%

“…This implied an effect of para-substitution of the PEA cation on the latter stage of hierarchical assembly [12,13]. [6,10]. Assigned numbers indicate priority based on the Cahn-Ingold-Prelog rules.…”

Section: Introductionmentioning

confidence: 99%

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Substituent Effects on the Crystal Structures of Salts Prepared from (R)-2-Methoxy-2-(1-naphthyl)propanoic Acid and (R)-1-Arylethylamines

2017

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Abstract:The crystal structures of salts 6-9 prepared from (R)-2-methoxy-2-(1-naphthyl)propanoicwere elucidated by X-ray crystallography. The solid-state associations and conformations of the MαNP salts were defined using the concepts of supramolecular-and planar chirality, respectively, and the crystal structures of salts 6-9 were interpreted as a three-step hierarchical assembly. The para-substituents of the (R)-1-arylethylammonium cations were found on sheet structures consisting of 2 1 columns. Thus, salts possessing smaller para-substituents, that is, salt 7 (p-F) and salt 9 (p-H), and larger para-substituents, that is, salt 6 (p-OMe) and salt 8 (p-Cl), crystallized in the space groups P2 1 and C2, respectively. Additionally, weak intermolecular interactions, that is, aromatic C-H···π, C-H···F, and C-H···O interactions, were examined in crystalline salts 6-9.

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Section: Saltmentioning

confidence: 98%

Section: Saltmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Substituent Effects on the Crystal Structures of Salts Prepared from (R)-2-Methoxy-2-(1-naphthyl)propanoic Acid and (R)-1-Arylethylamines

2017

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Nonsteroidal Anti-Inflammatory Drugs–1-Phenylethylamine Diastereomeric Salts: A Systematic Solid-State Investigation

Rossi

Ceccarelli

Milazzo

et al. 2021

Crystal Growth & Design

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The solid-state investigation of the diastereomeric salts (S)-ibuprofen (S-Ibu), (S)-naproxen, (S-Nap), and (S)-ketoprofen (S-Ket) with (R)-(+)- and (S)-(−)-1-phenylethylamine, R-PEA, and S-PEA respectively, has been carried out by using a combination of experimental and in-silico tools. The focus was on their crystal packing and on the stability/transformation of their solid forms under different experimental conditions with the final aim of extracting useful information on the forces/features which could be exploited for the chiral separation of the corresponding racemic compounds. All the salts are 21-column crystals, each column consisting of API and 1-phenylethylamine ions assembled via the 1-phenylethylammonium-carboxylate supramolecular heterosynthon which originates a R 4 3 (10) pattern, the intercolumns contacts being definitely weaker. In spite of an overall similarity in the crystal packing forces and motifs of the anhydrous salts, the temperature stability range suggests that the homochiral species are the most stable. The fact that the homochiral salt of S-Ket (S-Ket_S-PEA) is stable toward the hydration, at variance with the heterochiral one (S-Ket_R-PEA), further confirms this hypothesis. On the other hand, preliminary sorption tests show that S-Ket and S-Ibu preferentially capture the homochiral PEA (S-Nap is not selective). This behavior has been correlated to the almost planar boundary surfaces which characterize and differentiate the 21 sheets in S-Ket_S-PEA and S-Ibu_S-PEA salts with respect to the corresponding heterochiral ones.

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The Crystal Structure of the More-soluble Mosher’s Salt

Cited by 2 publications

References 27 publications

Substituent Effects on the Crystal Structures of Salts Prepared from (R)-2-Methoxy-2-(1-naphthyl)propanoic Acid and (R)-1-Arylethylamines

Substituent Effects on the Crystal Structures of Salts Prepared from (R)-2-Methoxy-2-(1-naphthyl)propanoic Acid and (R)-1-Arylethylamines

Nonsteroidal Anti-Inflammatory Drugs–1-Phenylethylamine Diastereomeric Salts: A Systematic Solid-State Investigation

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