H-Bonded anion-anion complexes in fentanyl citrate polymorphs and solvates

H-Bonded anion-anion complexes in fentanyl citrate polymorphs and solvates

Herein we report the experimental observation (X-ray characterization) of two different binding modes in H-bonded anion-anion complexes (anion = citrate) in N -(1-(2-phenylethyl)-4-piperidinylium)- N -phenyl-propanamide-citrate (fentanyl citrate). High level DFT calculations indicate that both types...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2019-01, Vol.55 (1), p.115-118
Hauptverfasser: Barbas, Rafael, Prohens, Rafel, Bauzá, Antonio, Franconetti, Antonio, Frontera, Antonio
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Sprache:eng
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Anions
Crystallography
Fentanyl
Mathematical analysis
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container_end_page 118
container_issue 1
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container_title Chemical communications (Cambridge, England)
container_volume 55
creator Barbas, Rafael
Prohens, Rafel
Bauzá, Antonio
Franconetti, Antonio
Frontera, Antonio
description Herein we report the experimental observation (X-ray characterization) of two different binding modes in H-bonded anion-anion complexes (anion = citrate) in N -(1-(2-phenylethyl)-4-piperidinylium)- N -phenyl-propanamide-citrate (fentanyl citrate). High level DFT calculations indicate that both types of anion-anion complexes (one with two and the other with four H-bonds) are thermodynamically unstable but kinetically stable with respect to the isolated anions with activation barriers as high as 14 kcal mol −1 . We report the experimental observation (X-ray characterization) of two types of anion-anion complexes (anion = dihydrogen citrate) stabilized by H-bonds that are observed in fentanyl citrate solvates.
doi_str_mv 10.1039/c8cc09028a
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Anions
Crystallography
Fentanyl
Mathematical analysis
title H-Bonded anion-anion complexes in fentanyl citrate polymorphs and solvates
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