Comparative 1H NMR chemical shift study on the stacking interaction of pyrimidine with purine and 6-methylpurine

Aradi, Ferenc

doi:10.1016/0301-4622(92)80047-9

Cited by 14 publications

(6 citation statements)

References 43 publications

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“…These results suggest that at low concentrations, when the stacks of sunset yellow are generally short, i.e. less than around 100 monomer units, 22 There are a number of reports in the literature describing aromatic stacking interactions between molecules with similar structures such as pyrimidines and purines, 45,46 purine and indoles, 47 and caffeine and adenosine. 28 Several of these studies employ more sophisticated versions of the isodesmic model, 28 incorporating …”

Section: Diffusion Behaviourmentioning

confidence: 86%

NMR Investigations of the Interaction Between the Azo-Dye Sunset Yellow and Fluorophenol

Katz

Day

2013

J. Phys. Chem. B

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Copyright and reuse:Sussex Research Online is a digital repository of the research output of the University.Copyright and all moral rights to the version of the paper presented here belong to the individual author(s) and/or other copyright owners. To the extent reasonable and practicable, the material made available in SRO has been checked for eligibility before being made available.Copies of full text items generally can be reproduced, displayed or performed and given to third parties in any format or medium for personal research or study, educational, or not-for-profit purposes without prior permission or charge, provided that the authors, title and full bibliographic details are credited, a hyperlink and/or URL is given for the original metadata page and the content is not changed in any way. [Abstract word count: 134]

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Section: Diffusion Behaviourmentioning

confidence: 86%

NMR Investigations of the Interaction Between the Azo-Dye Sunset Yellow and Fluorophenol

Katz

Day

2013

J. Phys. Chem. B

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“…Small aromatic molecules often undergo self-assembly in aqueous solution, driven by noncovalent interactions such as π–π stacking and the hydrophobic effect. , These interactions can result in dramatic changes to physicochemical properties, such as light absorption or solubility, and hence self-assembly phenomena have been the subject of much investigation, in areas as diverse as the impact on drug solubility and solvent partitioning, the intercalation of small molecules into DNA − and the propensity of some systems to form liquid crystals at high concentrations. − Typically, small molecule self-association is observed in aromatic systems where π–π stacking interactions are important, − or in amphipathic systems leading to micelle or other large assembly formation . Multicomponent systems are also important, probing the role of functional groups in aggregation − and drug delivery. − …”

Section: Introductionmentioning

confidence: 99%

“…[9][10][11][12][13] Typically, small molecule self-association is observed in aromatic systems where π-π stacking interactions are important, [14][15][16] or in amphipathic systems leading to micelle or other large assembly formation. 17 Multicomponent systems are also important, probing the role of functional groups in aggregation [18][19][20] and drug delivery. [21][22][23][24] A number of physical techniques can provide information on aggregation processes such as optical absorption, 3 x-ray scattering 3,13,25,26 and nuclear magnetic resonance (NMR) spectroscopy.…”

Section: Introductionmentioning

confidence: 99%

Influence of Structural Isomerism and Fluorine Atom Substitution on the Self-Association of Naphthoic Acid

Briffitt

Day

2015

J. Phys. Chem. B

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Article (Accepted Version) http://sro.sussex.ac.uk Briffitt, Roseanne and Day, Iain (2015) Influence of structural isomerism and fluorine atom substitution on the self-association of naphthoic acid. Journal of Physical Chemistry B, 119 (22). pp. 6703-6710. ISSN 1520-6106 This version is available from Sussex Research Online: http://sro.sussex.ac.uk/54128/ This document is made available in accordance with publisher policies and may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the URL above for details on accessing the published version. Copyright and reuse:Sussex Research Online is a digital repository of the research output of the University.Copyright and all moral rights to the version of the paper presented here belong to the individual author(s) and/or other copyright owners. To the extent reasonable and practicable, the material made available in SRO has been checked for eligibility before being made available.Copies of full text items generally can be reproduced, displayed or performed and given to third parties in any format or medium for personal research or study, educational, or not-for-profit purposes without prior permission or charge, provided that the authors, title and full bibliographic details are credited, a hyperlink and/or URL is given for the original metadata page and the content is not changed in any way. AbstractThe self-association of small aromatic systems driven by π-π stacking and hydrophobic interactions is well known. Understanding the nature of these interactions is important if they are to be used to control association. Here, we present results of an NMR study into the self-association of two isomers of naphthoic acid along with an investigation into the role of a fluorine substituent on that selfassociation. We interpret the results in terms of a simple isodesmic model of selfassociation and show that the addition of the fluorine atom appears to increase the stability of the aggregates by an order of magnitude (e.g. 1-naphothic acid vs 4-fluoro-1-naphthoic acid K eq = 0.05 increases to 0.35 M -1 ), a result which is supported by computational studies in the literature on the role of substituent effects on interaction energy. The use of fluorinated isomers to probe the assembly is also presented, with differing trends in fluorine-19 chemical shifts observed depending on the isomer substitution pattern.3

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“…The tendency to hetero-association was found to depend strongly on the type of substituents; for example, K h increases with methylation of purine and pyrimidine bases, which was interpreted in terms of either greater hydrophobic or van der Waals contribution to the thermodynamics of complexation [70,[83][84][85][86]98]. However, methylation also leads to alterations in the structures of 1:1 hetero-complexes due to the steric demands to accommodate the methyl group within the complex (an increase in distance and induction of partial overlap between the chromophores) [85,101].…”

Section: Hetero-association Of Derivatives Of Nucleic Acid Basesmentioning

confidence: 99%

“…In general, the derived magnitudes of the equilibrium hetero-association constants (K h ) have values in between the self-association constants of the interacting compounds [23, 27, 70, 85-87, 98, 99], except for a very few reports [27,84,100] which, however, were not linked to the physico-chemical properties of the interacting molecules. It was found that K h for the interaction of purine derivatives is, on average, higher than that for purine-pyrimidine which, in turn, is much greater than for pyrimidine-pyrimidine interactions [23,84,87,98]. Based on these results, it was concluded that hetero-association of derivatives of nucleic acid bases in water is largely governed by van der Waals interactions between the molecules in hetero-complexes, which are known to correlate with the dimensions of aromatic portion of the interacting molecules [11,86,87].…”

Section: Hetero-association Of Derivatives Of Nucleic Acid Basesmentioning

confidence: 99%

Hetero-association of aromatic molecules in aqueous solution

Evstigneev

2014

International Reviews in Physical Chemistry

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Knowledge of the physical chemistry of small molecules complexation (the hetero-association) in aqueous solution is increasingly important in view of the rapidly emerging branch of supramolecular chemistry dealing with the formation of heterogeneous polymeric structures having specific functional roles. In this paper, the 50-year history of scientific studies of hetero-association of heterocyclic aromatic molecules in aqueous solution has been reviewed. Some important correlations of structural and thermodynamic parameters of complexation have been reported based on large data-set of hetero-association parameters accumulated to date. The fundamental problem of 'energetic composition' of π-stacking is extensively discussed. The review has shown that there are some gaps in our understanding of heteroassociation, which provides a challenge for further studies in this area.

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Comparative 1H NMR chemical shift study on the stacking interaction of pyrimidine with purine and 6-methylpurine

Cited by 14 publications

References 43 publications

NMR Investigations of the Interaction Between the Azo-Dye Sunset Yellow and Fluorophenol

NMR Investigations of the Interaction Between the Azo-Dye Sunset Yellow and Fluorophenol

Influence of Structural Isomerism and Fluorine Atom Substitution on the Self-Association of Naphthoic Acid

Hetero-association of aromatic molecules in aqueous solution

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