2012
DOI: 10.1039/c2ce06439a
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An experimental screen for quinoline/fumaric acid salts and co-crystals

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Cited by 16 publications
(4 citation statements)
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“…Depending on the choice of the pyridine-containing compound, the neutral or ionic nature of the resulting two-component system of gallic acid mostly follows the pKa rule [55,[91][92][93][94] stating that a salt is formed if ∆pKa > 3 and a co-crystal, if ∆pKa < −1 (Table S6 of Supplementary Materials). The exceptions are the salt of 4,4 -ethylenedipyridin (DUTJEI), which is obtained with lattice water molecules [65] to affect the pKa values of the components [95], and of isoniazid (LODHIX and LODHOD), which is a superposition of a salt and a co-crystal not attained at the highest accessed temperature [64], as well as the previously reported co-crystal 1 [63] and its new solvatomorph 2.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Depending on the choice of the pyridine-containing compound, the neutral or ionic nature of the resulting two-component system of gallic acid mostly follows the pKa rule [55,[91][92][93][94] stating that a salt is formed if ∆pKa > 3 and a co-crystal, if ∆pKa < −1 (Table S6 of Supplementary Materials). The exceptions are the salt of 4,4 -ethylenedipyridin (DUTJEI), which is obtained with lattice water molecules [65] to affect the pKa values of the components [95], and of isoniazid (LODHIX and LODHOD), which is a superposition of a salt and a co-crystal not attained at the highest accessed temperature [64], as well as the previously reported co-crystal 1 [63] and its new solvatomorph 2.…”
Section: Resultsmentioning
confidence: 99%
“…In these co-crystals, the appropriate hydroxylpyridine adopts its keto-form (Scheme S1 of Supplementary Materials) preferred in the crystal state [67,68], thereby precluding the proton transfer to the nitrogen atom and the formation of a predicted salt. In the case of the salt 4 and a few reported co-crystals (XUMHUL, YAHTUY, AYIWEM, TUZFAX, and TUZFEB) and salts (TICZIQ, TUZDUP, and EHUGOE), the ∆pKa value for the two components is between −1 and 3 (Table S6 of Supplementary Materials), which is the gray zone for the prediction of the proton transfer [55,64,86,[92][93][94]96], so the formation of the salt and of the co-crystal is equally plausible.…”
Section: Resultsmentioning
confidence: 99%
“…On the other hand, ∆pK a of PN-PABA/PHBA/PCBA/INH/PNBA systems is between 0 and 3, the grey zone wherein the formation of salt/cocrystal for the combination cannot be predicted. 10,23,27,[39][40][41][43][44][45][46][47][48] In addition, the possibility of a mixed-ionic complex 14 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 4 cocrystal can be classified as a conjugate acid-base (CAB) cocrystal 11,52,53 since the adduct consists of PNBA and its conjugate base PNB -in the crystal structure (described later). Crystal structures of PN-PABA/PHBA/PCBA/PNBA/SAC adducts (their crystallographic parameters are given in Table 2) are discussed next followed by binary phase diagrams of PN-NA/INH eutectics.…”
Section: Resultsmentioning
confidence: 99%
“…1,2 Fumaric acid has traditionally been used in the production of food acidity regulators, 1 feed preservatives, 35 and other high-potency chemical products. 68 Recently, fumaric acid has been applied in metal–organic frameworks, 9,10 polymer composites, 11,12 composite anodes of high-energy lithium batteries, 13 co-crystals, 14,15 and microenvironment tablets. 16 Thus, the demand for fumaric acid has dramatically increased with the expansion of the application scope for fumaric acid, which has made it necessary to study effective fumaric acid production methods.…”
Section: Introductionmentioning
confidence: 99%