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

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Abstract

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.

Graphical abstract: H-Bonded anion–anion complexes in fentanyl citrate polymorphs and solvates

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Publication details

The article was received on 13 Nov 2018, accepted on 26 Nov 2018 and first published on 27 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC09028A
Citation: Chem. Commun., 2019, Advance Article
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    H-Bonded anion–anion complexes in fentanyl citrate polymorphs and solvates

    R. Barbas, R. Prohens, A. Bauzá, A. Franconetti and A. Frontera, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C8CC09028A

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