Off-Center Oxygen−Arene Interactions in Solution:  A Quantitative Study

Gung, Benjamin W.; Xue, Xiaowen; Reich, Hans J.

doi:10.1021/jo050874+

Cited by 51 publications

(42 citation statements)

References 29 publications

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“…8c) 86,94 . The relative populations of the syn and anti conformers, which were readily determined by 1 H NMR spectroscopy, were expected to be dictated by the lp–π interaction strength between the C9 benzyl and the C1 methoxymethyl (MOM) substituent.…”

Section: Lone Pair–π Interactionsmentioning

confidence: 99%

Exploiting non-covalent π interactions for catalyst design

Neel

Hilton

Sigman

et al. 2017

Nature

680

447

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Molecular recognition, binding and catalysis are often mediated by non-covalent interactions involving aromatic functional groups. Although the relative complexity of these so-called π interactions has made them challenging to study, theory and modelling have now reached the stage at which we can explain their physical origins and obtain reliable insight into their effects on molecular binding and chemical transformations. This offers opportunities for the rational manipulation of these complex non-covalent interactions and their direct incorporation into the design of small-molecule catalysts and enzymes.

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Section: Lone Pair–π Interactionsmentioning

confidence: 99%

Exploiting non-covalent π interactions for catalyst design

Neel

Hilton

Sigman

et al. 2017

Nature

680

447

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“… Illustration of the conformational equilibrium between syn and anti rotamers of triptycene derivative 16 a . Triptycenes 16 b with R=CH 3 , COH, COCH 3 , COC 2 H 5 , COCH(CH 3 ) 2 , COCF 3 and X=H, F, CN, CH 3 , CF 3 were also studied …”

Section: Triptycene Balances Of ōKi and Gungmentioning

confidence: 99%

“…Triptycenes 16 b (Figure ) with R=CH 3 , COH, COCH 3 , COC 2 H 5 , COCH(CH 3 ) 2 , COCF 3 and X=H, F, CN, CH 3 , CF 3 were also used to determine the strength of LP⋅⋅⋅aryl forces in the off‐centre arrangement . For R=Me and X=CF 3 , a relatively strong attractive interaction was observed (−1.97 kJ mol −1 ), whereas for R=COCF 3 and X=H the interaction was repulsive (+0.33 kJ mol −1 ).…”

Section: Triptycene Balances Of ōKi and Gungmentioning

confidence: 99%

Some Recent Advances in the Design and Use of Molecular Balances for the Experimental Quantification of Intramolecular Noncovalent Interactions of π Systems

Aliev

Motherwell

2019

Chemistry A European J

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Herein, various molecular balances used for comparing the strengths of intramolecular noncovalent interactions are reviewed. Our overview indicates that considerable quantitative insight into the strength of noncovalent interactions can be gained through the careful design of molecular balances. Many exciting opportunities certainly exist for the design of further new balances to quantify and dissect the relative strengths of noncovalent interactions as a function of solvation and the importance of the many factors that contribute to overall molecular recognition. However, even simple model molecules can show a multiplicity of intramolecular noncovalent interactions acting in a combined fashion. It is therefore essential to undertake a detailed computational analysis to identify all possible noncovalent interactions present in a selected molecular balance prior to a quantitative experimental assessment of the strength of a particular noncovalent interaction. It is also argued that the words “torsion” and “molecular balance” seem to have become inextricably linked and, in consequence, even top pan and seesaw balances have been mistakenly referred to in these terms.

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“…Considerable recent attention is focused on weak molecular complexes involving aromatic rings . Interest in such complexes stems from the fact that they play a vital role in chemistry, molecular biology, and materials science.…”

Section: Introductionmentioning

confidence: 99%

Noncovalent interactions involving aromatic rings: correlation analysis via substituent constants

Кузнецова

Egorochkin

Хамалетдинова

et al. 2016

J. Phys. Org. Chem.

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The elucidation of the mechanism of the substituent influence on the properties P (the interaction energies E, interring distances l, and free energies ΔG of interaction) of weak complexes involving aromatic rings is of importance not only theoretically but also from a practical standpoint. This mechanism is little understood. In this work, the literature data on the substituent influence on P properties for 42 series of complexes have been analyzed, using correlation analysis. Generally, the inductive, resonance, polarizability, and steric effects are in operation. The presence or absence of certain effects and the relation between their contributions are determined by the type of series. The polarizability effect (an electrostatic ion‐dipole interaction) is caused by an excess charge appearing on the ring substituted fragment of complexes as a result of the complexation. This effect is observed in all series; its contribution ranges up to approximately 50%.

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Off-Center Oxygen−Arene Interactions in Solution: A Quantitative Study

Cited by 51 publications

References 29 publications

Exploiting non-covalent π interactions for catalyst design

Exploiting non-covalent π interactions for catalyst design

Some Recent Advances in the Design and Use of Molecular Balances for the Experimental Quantification of Intramolecular Noncovalent Interactions of π Systems

Noncovalent interactions involving aromatic rings: correlation analysis via substituent constants

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