University of Sussex
Browse
forSRO.pdf (2.59 MB)

Influence of structural isomerism and fluorine atom substitution on the self-association of naphthoic acid

Download (2.59 MB)
journal contribution
posted on 2023-06-08, 20:53 authored by Roseanne Briffitt, Iain Day
The self-association of small aromatic systems driven by p-p 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 self- association. We interpret the results in terms of a simple isodesmic model of self- association 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 Keq = 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.

History

Publication status

  • Published

File Version

  • Accepted version

Journal

Journal of Physical Chemistry B

ISSN

1520-6106

Publisher

American Chemical Society

Issue

22

Volume

119

Page range

6703-6710

Department affiliated with

  • Chemistry Publications

Full text available

  • Yes

Peer reviewed?

  • Yes

Legacy Posted Date

2015-05-22

First Open Access (FOA) Date

2016-05-15

First Compliant Deposit (FCD) Date

2015-05-22

Usage metrics

    University of Sussex (Publications)

    Categories

    No categories selected

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC