Inclusion of 1,4-bis(diphenylhydroxymethyl)benzene with amides: structure and selectivity

Jacobs, Ayesha; Nassimbeni, Luigi R.; Silwana, Nothemba; Báthori, Nikoletta B.; Weber, Edwin

doi:10.1039/c1ce05647f

Cited by 4 publications

(1 citation statement)

References 12 publications

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“…Since then, other compounds that may be described as wheel-and-axle molecules have been designed, synthesized, and investigated for their inclusion abilities. More recently, 1,4-bis(diphenylhydroxymethyl)benzene ( H , Scheme ), also with wheel-and-axle characteristics, was reported by the research teams of Nassimbeni (2011) and Bacchi (2017) to possess host properties for various N-alkylated amides and nicotine, respectively. However, H was first reported as a successful host compound by Toda and co-workers in 1989 .…”

Section: Introductionmentioning

confidence: 99%

Behavior of the Wheel-and-Axle Host Compound 1,4-Bis(diphenylhydroxymethyl)benzene in Mixed Pyridyl Guest Solvents

Barton,

Vorgers,

Hosten

2023

Crystal Growth & Design

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The host ability of the wheel-and-axle compound, 1,4-bis-(diphenylhydroxymethyl)benzene H, was extensively investigated in pure pyridine (PYR), 2-methylpyridine (2MP), 3-methylpyridine (3MP), and 4methylpyridine (4MP) guest pyridines; each one was enclathrated with 1:2 H/G ratios. H was then presented with mixed guest solvents, both equimolar and binary non-equimolar solutions, and it was observed that this host compound possesses the ability to separate or purify a great number of these various mixtures. The selectivity of H was demonstrated to be significantly in favor of PYR and 4MP dependent on the type and amount of each guest present in the solution. The crystal structures of the four single-solvent complexes were obtained by employing SCXRD analyses, which also assisted in understanding the host selectivity behavior in these mixed solvents. Hirshfeld surface investigations demonstrated that the preferred guest species, PYR and 4MP, experienced a greater percentage of (guest)N•••H−O(host) interactions than was observed for the guests less preferred (2MP and 3MP). Finally, data from thermal analyses concurred with some, but not all, of the observations made from the mixed guest solvent competition experiments.

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Section: Introductionmentioning

confidence: 99%

Behavior of the Wheel-and-Axle Host Compound 1,4-Bis(diphenylhydroxymethyl)benzene in Mixed Pyridyl Guest Solvents

Barton,

Vorgers,

Hosten

2023

Crystal Growth & Design

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Investigation of the hydrogen bonded host‧‧‧guest and guest‧‧‧guest interactions present in complexes of a polyaromatic wheel-and-axle host compound with dioxane, morpholine, piperidine and pyridine

Barton,

Caira,

Vorgers

et al. 2023

J Incl Phenom Macrocycl Chem

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Abstract1,4-Bis(diphenylhydroxymethyl)benzene (H), a host compound possessing wheel-and-axle geometry, was found to possess host ability for dioxane (DIO), morpholine (MOR) and piperidine (PIP), forming inclusion compounds with each one with 1:2 host:guest ratios. This observation prompted an investigation of the host behaviour in mixtures of these guest compounds but where pyridine (PYR) was also considered (PYR was reported earlier to also form a 1:2 complex with H). In mixtures, H demonstrated significant affinities for, more especially, MOR and PIP, while DIO and PYR were usually disfavoured guest species. Single crystal X-ray diffraction experiments revealed that MOR (a favoured guest species) interacted by means of three hydrogen bonds with both adjacent guest and host molecules, plausibly explaining the host preference for this guest species; each of DIO, PYR and PIP were involved in only one interaction of this type with H. Total energy calculations revealed that the host-guest molecular pairs involving preferred MOR and PIP possessed significantly lower energies than those with disfavoured DIO and PYR. Thermal analyses demonstrated that the complex containing the least favoured guest compound, H‧2(DIO), possessed the lowest thermal stability of the four complexes, but these experiments did not clearly explain the affinity of H for MOR.

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Inclusion and selectivity of amides by p-terphenyl derivative bearing adamantanecarboxylic acid

et al. 2018

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Inclusion of 1,4-bis(diphenylhydroxymethyl)benzene with amides: structure and selectivity

Cited by 4 publications

References 12 publications

Behavior of the Wheel-and-Axle Host Compound 1,4-Bis(diphenylhydroxymethyl)benzene in Mixed Pyridyl Guest Solvents

Behavior of the Wheel-and-Axle Host Compound 1,4-Bis(diphenylhydroxymethyl)benzene in Mixed Pyridyl Guest Solvents

Investigation of the hydrogen bonded host‧‧‧guest and guest‧‧‧guest interactions present in complexes of a polyaromatic wheel-and-axle host compound with dioxane, morpholine, piperidine and pyridine

Inclusion and selectivity of amides by p-terphenyl derivative bearing adamantanecarboxylic acid

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