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@ARTICLE{Tsapatsaris:201731,
author = {Tsapatsaris, Nikolaos and Kolesov, Boris A. and Fischer,
Jennifer and Boldyreva, Elena V. and Daemen, Luke and
Eckert, Juergen and Bordallo, Heloisa N.},
title = {{P}olymorphism of {P}aracetamol: {A} {N}ew {U}nderstanding
of {M}olecular {F}lexibility through {L}ocal {M}ethyl
{D}ynamics},
journal = {Molecular pharmaceutics},
volume = {11},
number = {3},
issn = {1543-8392},
address = {Washington, DC},
publisher = {American Chemical Society},
reportid = {FZJ-2015-04025},
pages = {1032 - 1041},
year = {2014},
abstract = {This study focuses on the interplay of molecular
flexibility and hydrogen bonding manifested in the
monoclinic (form I) and orthorhombic (form II) polymorphs of
paracetamol. By means of incoherent inelastic neutron
scattering and density functional theory calculations, the
relaxation processes related to the methyl side-group
reorientation were analyzed in detail. Our computational
study demonstrates the importance of considering quantum
effects to explain how methyl reorientations and subtle
conformational changes of the molecule are intertwined.
Indeed, by analyzing the quasi elastic signal of the neutron
data, we were able to show a unique and complex motional
flexibility in form II, reflected by a coupling between the
methyl and the phenyl reorientation. This is associated with
a higher energy barrier of the methyl rotation and a lower
Gibbs free energy when compared to form I. We put forward
the idea that correlating solubility and molecular
flexibility, through the relation between pKa and methyl
rotation activation energy, might bring new insights to
understanding and predicting drug bioavailability.},
cin = {ICS-1 / Neutronenstreuung ; JCNS-1},
ddc = {540},
cid = {I:(DE-Juel1)ICS-1-20110106 / I:(DE-Juel1)JCNS-1-20110106},
pnm = {451 - Soft Matter Composites (POF2-451) / 54G - JCNS
(POF2-54G24)},
pid = {G:(DE-HGF)POF2-451 / G:(DE-HGF)POF2-54G24},
typ = {PUB:(DE-HGF)16},
UT = {WOS:000332348600036},
doi = {10.1021/mp400707m},
url = {https://juser.fz-juelich.de/record/201731},
}