Impact of Intermolecular Interactions, Dimeric Structures on the Glass Forming Ability of Naproxen, and a Series of Its Derivatives
PBN-AR
Instytucja
Wydział Matematyki, Fizyki i Chemii (Uniwersytet Śląski w Katowicach)
Informacje podstawowe
Główny język publikacji
EN
Czasopismo
MOLECULAR PHARMACEUTICS (45pkt w roku publikacji)
ISSN
1543-8384
EISSN
Wydawca
AMER CHEMICAL SOC
DOI
URL
Rok publikacji
2018
Numer zeszytu
10
Strony od-do
4764-4776
Numer tomu
15
Liczba arkuszy
0,60
Słowa kluczowe
EN
crystallization kinetics
glass forming ability
molecular dynamics
naproxen derivatives
Streszczenia
Język
EN
Treść
In this article, thermal properties, molecular dynamics, crystallization kinetics, and intermolecular interactions in pure naproxen (NAP), its amide (NH2–NAP), and four esters (methyl, Met-NAP; isopropyl, Iso-NAP; hexyl, Hex-NAP; and benzyl, Ben-NAP) have been investigated using differential scanning calorimetry as well as broadband dielectric and Fourier transform infrared spectroscopies. We found that the modification of the NAP molecule by substituting a hydrogen atom from the hydroxyl group strongly inhibits the crystallization tendency of this active pharmaceutical ingredient (API) and simultaneously increases its glass forming ability (GFA). In this context, it is worthwhile to stress that pure naproxen and its amide crystallized very quickly, regardless of the cooling rate. Therefore, these compounds cannot be classified as good glass-formers. On the other hand, ester derivatives of API can be easily vitrified. Moreover, dielectric measurements revealed that with an increasing molecular weight of the substituent, the rate of crystallization process slows down significantly. Consequently, Ben-NAP was characterized by the highest GFA among all investigated API esters. Comprehensive FTIR studies clearly indicated that the strong tendency to create dimeric structures in the nonmodified NAP and NH2–NAP is responsible for their enhanced crystallization. At the first sight, our results stay in contrast to most literature data, showing that H-bonds favor the glass formation ability. However, this effect is usually observed for the materials, which form extensive multidirectional hydrogen bonds and associates. In NAP and NH2–NAP, the situation is much different, since both compounds exist mainly as dimers. Therefore, one can postulate that specific intermolecular interactions are an important parameter determining the GFA of different materials, including APIs.
Cechy publikacji
original-article
Inne
System-identifier
3342900147769
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