Host compounds (+)-(2R,3R)-1,1,4,4-tetraphenylbutane-1,2,3,4-tetraol (TETROL) and (2R,3R)-(−)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol (DMT) with guests o-, m- and p- toluidine: A comparative investigation

Barton, Benita; Dorfling, Sasha-Lee; Hosten, Eric C.; Pohl, Pieter L.

doi:10.1016/j.tet.2018.04.039

Cited by 9 publications

(5 citation statements)

References 19 publications

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“…In fact, the three complexes are isostructural with nearly identical unit cell axes lengths and angles. Remarkably, H2 only ever crystallized with the same host packing irrespective of whether the guests were xylenes and ethylbenzene, 2 anilines and N-methylated anilines, 20 toluidines, 21 alkylbenzenes, 22 nitroaromatics, 23 and anisoles. 24 The unit cell for these inclusion compounds is provided in Fig.…”

Section: Single Crystal X-ray Diffraction (Scxrd) Experimentsmentioning

confidence: 99%

An investigation of the selectivity behaviour of host compound (R,R)-(−)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol in mixed cresols

2023

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Section: Single Crystal X-ray Diffraction (Scxrd) Experimentsmentioning

confidence: 99%

An investigation of the selectivity behaviour of host compound (R,R)-(−)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol in mixed cresols

2023

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“…Note that other binary guest combinations, which ordinarily contained disfavored guests o TOL or TOL, failed to furnish crystals, and so the host selectivity profiles could not be ascertained in these instances. Furthermore, p TOL/ o TOL and p TOL /m TOL experiments also provided such profiles and showed that p TOL was significantly favored in both cases, in the former more so than in the latter; these results have been submitted for publication …”

Section: Results and Discussionmentioning

confidence: 72%

“…Furthermore, pTOL/oTOL and pTOL/mTOL experiments also provided such profiles and showed that pTOL was significantly favored in both cases, in the former more so than in the latter; these results have been submitted for publication. 18 From Figure 1a, it is clear that TETROL favors ANI over the entire concentration range when this solvent competes with mTOL, except at very low concentrations of ANI (≤4%), where the host displayed very low selectivity. The selectivity coefficient, K G1:G2 , which is given by 19…”

Section: Resultsmentioning

confidence: 96%

Hydrogen Bonding, the Driving Force for Increased Host Selectivities in Two-Solvent Mixed Complexes of TETROL Comprising Both Favored (Aniline) and Disfavored Guests (o-Toluidine or Toluene)

Barton

Dorfling

Hosten

2018

Crystal Growth & Design

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In this work, we have shown that host−guest hydrogen bonding is intricately associated with host selectivity in supramolecular systems comprising host (+)-(2R,3R)-1,1,4,4-tetraphenylbutane-1,2,3,4-tetraol (TETROL) and guests aniline, toluene, and the toluidines. Competition experiments provided the host selectivity order, p-toluidine > aniline > m-toluidine > o-toluidine > toluene and, additionally, three crystalline two-guest mixed complexes containing aniline/ o-toluidine, aniline/p-toluidine, and aniline/toluene; the overall host:guest ratio was 2:3. Crystal diffraction experiments showed the host packing to be consistently isostructural. Furthermore, only two of the three guests in the asymmetric unit are hydrogen bonded to the host; the third does not experience this interaction type even if possessing hydrogen-bonding capability (e.g., an amino functionality). In the TETROL/aniline/ o-toluidine and TETROL/aniline/toluene mixed complexes comprising both favored (aniline) and disfavored (o-toluidine or toluene) guests, it is exclusively the former that are accommodated in the two hydrogen-bonding sites, while the third location, where hydrogen bonding with the host is absent, is able to contain both guest types. However, each of the three sites in the mixed complex containing only favored guests (TETROL/aniline/p-toluidine) is able to clathrate both species. These observations explain the increased site occupancy factors of preferred guests in the crystal and hence the selectivity of the host.

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“…The focus in our laboratories has been on the latter application type. It has been demonstrated that this field of science may be employed to separate, for example, the C8 aromatic fraction of crude oil, the methylpyridines, the dichlorobenzenes, the methylanisoles, various anilines, and the toluidines, from one another [17][18][19][20][21][22][23]. Successful host compounds were derived from xanthone, thioxanthone, anthracene and tartaric acid.…”

Section: Introductionmentioning

confidence: 99%

Exploring the host compound dynamics of 1,4-phenylene-bis(di-p-fluorophenylmethanol) in mixed pyridines

Barton,

Vorgers,

Hosten

2024

Preprint

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In this investigation, the wheel-and-axle host compound, 1,4-phenylene-bis(di-p-fluorophenylmethanol) H, was demonstrated to have inclusion ability for each of PYR, 2MP, 3MP and 4MP (1:1, 1:2, 1:2 and 1:2 were the H:G ratios). In the equimolar guest competition experiments, H was observed to have an overwhelming affinity for PYR and 4MP relative to 2MP and 3MP. In fact, selectivity coefficients calculated from the non-equimolar binary guest competition experiments suggested that this host compound would be an efficient candidate for the separation of all PYR/2MP mixtures and a 40:60 4MP/3MP solution through host-guest chemistry strategies. SCXRD analyses established the preferred guests (PYR and 4MP) to be involved in significantly shorter stabilizing classical hydrogen bonding interactions with H, explaining the selectivity behaviour of this host compound in the guest mixtures. Additionally, Hirshfeld surface considerations also explained this behaviour, but only for PYR. Additionally, thermal analyses were used to ascertain the relative thermal stabilities of the four complexes and, satisfyingly, the PYR- and 4MP-containing complexes possessed the greater thermal stabilities compared with H·2(2MP) and H·2(3MP), as was demonstrated by a comparison of their guest release onset temperatures.

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Host compounds (+)-(2R,3R)-1,1,4,4-tetraphenylbutane-1,2,3,4-tetraol (TETROL) and (2R,3R)-(−)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol (DMT) with guests o-, m- and p- toluidine: A comparative investigation

Cited by 9 publications

References 19 publications

An investigation of the selectivity behaviour of host compound (R,R)-(−)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol in mixed cresols

An investigation of the selectivity behaviour of host compound (R,R)-(−)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol in mixed cresols

Hydrogen Bonding, the Driving Force for Increased Host Selectivities in Two-Solvent Mixed Complexes of TETROL Comprising Both Favored (Aniline) and Disfavored Guests (o-Toluidine or Toluene)

Exploring the host compound dynamics of 1,4-phenylene-bis(di-p-fluorophenylmethanol) in mixed pyridines

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