Aqueous solubility study of salts of benzylamine derivatives and p-substituted benzoic acid derivatives using X-ray crystallographic analysis
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Aqueous solubility study of salts of benzylamine derivatives and p-substituted benzoic acid derivatives using X-ray crystallographic analysis. / Parshad, Henrik; Frydenvang, Karla Andrea; Liljefors, Tommy; Sorensen, Henning Osholm; Larsen, Claus.
In: International Journal of Pharmaceutics, Vol. 269, No. 1, 2004, p. 157-68.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Aqueous solubility study of salts of benzylamine derivatives and p-substituted benzoic acid derivatives using X-ray crystallographic analysis
AU - Parshad, Henrik
AU - Frydenvang, Karla Andrea
AU - Liljefors, Tommy
AU - Sorensen, Henning Osholm
AU - Larsen, Claus
PY - 2004
Y1 - 2004
N2 - Twenty two p-substituted benzoic acid derivates were used to prepare salts of N-methylbenzylamine (II) and N,N-dimethylbenzylamine (III), respectively. Only five salts of (II) and two salts of (III) were obtained in a crystalline state. The solubility of these salts was orders of magnitude higher than those reported for the corresponding salts of benzylamine (I). Thermal analysis indicated that the increased solubility was caused by reduced crystal lattice energy, which was most likely due to the reduced number of strong hydrogen bonds of the salt of (II) and (III). X-ray crystallographic analysis of p-hydroxybenzoic acid salt of (I), (II) and (III) suggested that the reduced number of hydrogen bonds caused the apparent higher solubility. Further analyses of seven salts of (I) were performed. It was not possible to identify any relationship between the number of hydrogen bonds and the corresponding solubility of the salts.
AB - Twenty two p-substituted benzoic acid derivates were used to prepare salts of N-methylbenzylamine (II) and N,N-dimethylbenzylamine (III), respectively. Only five salts of (II) and two salts of (III) were obtained in a crystalline state. The solubility of these salts was orders of magnitude higher than those reported for the corresponding salts of benzylamine (I). Thermal analysis indicated that the increased solubility was caused by reduced crystal lattice energy, which was most likely due to the reduced number of strong hydrogen bonds of the salt of (II) and (III). X-ray crystallographic analysis of p-hydroxybenzoic acid salt of (I), (II) and (III) suggested that the reduced number of hydrogen bonds caused the apparent higher solubility. Further analyses of seven salts of (I) were performed. It was not possible to identify any relationship between the number of hydrogen bonds and the corresponding solubility of the salts.
KW - Benzoic Acids
KW - Benzylamines
KW - Chemistry, Physical
KW - Crystallography, X-Ray
KW - Hydrogen Bonding
KW - Molecular Conformation
KW - Physicochemical Phenomena
KW - Solubility
KW - Water
M3 - Journal article
C2 - 14698587
VL - 269
SP - 157
EP - 168
JO - International Journal of Pharmaceutics
JF - International Journal of Pharmaceutics
SN - 0378-5173
IS - 1
ER -
ID: 40371323