Fatty acids polymorphism and solid-state miscibility

Gbabode, Gabin; Négrier, Philippe; Mondieig, D.; Granell, Enric Marco; Calvet, Teresa; Cuevas‐Diarte, M. A.

doi:10.1016/j.jallcom.2008.02.047

Cited by 21 publications

(6 citation statements)

References 36 publications

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“…The repeat distance of the stripe-normal order of our o2 monolayer, 48.3 Å (Table 2) is greater than the average dimer lengths measured for the rich array of polymorphs exhibited by 3D crystals of monocarboxylic fatty acids. 23,63,72 These effective dimer lengths range from 44.3 Å for the B phase, which includes one gauche conformation per molecule, 72,73 to 44.9 Å of the most stable, all-trans, C phase, 23,26,62 to 45.7 Å for the rather rare E phase. 63,68,72 Using the C phase as a typical value, the 3.4 Å larger repeat distance of our o2 LF can be well-accounted for by the proposed inclusion of an Hg atom in the carboxylÀcarboxyl dimer bond, as discussed above.…”

Section: Discussionmentioning

confidence: 99%

Hydrogen-Bonded Order in Mercury-Supported Monolayers of End-Functionalized Alkanes

et al. 2011

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The order formed by hydrogen bonding in mercury-supported Langmuir films (LFs) of end-functionalized, surface-parallel, alkane molecules was studied by surface-specific X-ray methods and surface tensiometry. Hexadecane derivatives, substituted at one or both ends by mercapto, carboxy, or hydroxy moieties were studied. The dimensionality of the monolayer's surface-parallel order was found to correspond to the number of molecular carboxyl groups, with the zero-, one-, or two-carboxyl molecules exhibiting no, one-, or two-dimensional order, respectively. The observed structural motifs are rationalized based on the molecular conformations and bonding synthons. Similarities, or otherwise, with the corresponding structure of three-dimensional (3D) crystals and graphite-supported LFs are also discussed.

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Section: Discussionmentioning

confidence: 99%

Hydrogen-Bonded Order in Mercury-Supported Monolayers of End-Functionalized Alkanes

et al. 2011

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“…2,3 Acids containing an even number of carbons crystallize in at least seven different phases designated A 2 , A super , B m , B o , E m , E o , and C. 4 The n -alkyl acids having an odd number of carbons crystallize in at least five distinct phases denoted A’, B’, C’, C” and D’. 5 While the phases of many n -alkyl monocarboxylic acids have been characterized crystallographically, others remain relatively unstudied. For example, palmitic acid (C 16 H 32 O 2 ) has only one reported crystalline phase.…”

Section: Introductionmentioning

confidence: 99%

Predicting anisotropic thermal displacements for hydrogens from solid-state NMR: a study on hydrogen bonding in polymorphs of palmitic acid

Wang

Uribe‐Romo

Mueller

et al. 2018

Phys. Chem. Chem. Phys.

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The hydrogen-bonding environments at the COOH moiety in eight polycrystalline polymorphs of palmitic acid are explored using solid-state NMR. Although most phases have no previously reported crystal structure, measured 13C chemical shift tensors for COOH moieties, combined with DFT modeling establish that all phases crystallize with a cyclic dimer (R22(8)) hydrogen bonding arrangement. Phases A2, Bm and Em have localized OH hydrogens while phase C has a dynamically disordered OH hydrogen. The phase designated As is a mix of five forms, including 27.4% of Bm and four novel phases not fully characterized here due to insufficient sample mass. For phases A2, Bm, Em, and C the anisotropic uncertainties in the COOH hydrogen atom positions are established using a Monte Carlo sampling scheme. Sampled points are retained or rejected at the ±1σ level based upon agreement of DFT computed 13COOH tensors with experimental values. The collection of retained hydrogen positions bear a remarkable resemblance to the anisotropic displacement parameters (i.e. thermal ellipsoids) from diffraction studies. We posit that this similarity is no mere coincidence and that the two are fundamentally related. The volumes of NMR-derived anisotropic displacement ellipsoids for phases with localized OH hydrogens are 4.1 times smaller than those derived from single crystal X-ray diffraction and 1.8 times smaller than the volume of benchmark single crystal neutron diffraction values.

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“…Saturated carboxylic acids show polymorphism in the solid state. At least seven solid phases exist for the even members [12], called A2, Asuper, Bo, Bm, Eo, Em and C and five for the odd-numbered [13] called A', B', C', C'' and D'.…”

Section: Introductionmentioning

confidence: 99%

Case of Charge-Assisted Hydrogen Bonding in the Crystal Structure of Sodium Laurate, Lauric Acid

et al. 2022

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Fatty acids polymorphism and solid-state miscibility

Cited by 21 publications

References 36 publications

Hydrogen-Bonded Order in Mercury-Supported Monolayers of End-Functionalized Alkanes

Hydrogen-Bonded Order in Mercury-Supported Monolayers of End-Functionalized Alkanes

Predicting anisotropic thermal displacements for hydrogens from solid-state NMR: a study on hydrogen bonding in polymorphs of palmitic acid

Case of Charge-Assisted Hydrogen Bonding in the Crystal Structure of Sodium Laurate, Lauric Acid

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