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

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

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Abstract

The 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 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.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry
Q Science > QD Chemistry > QD0450 Physical and theoretical chemistry
Depositing User: Iain Day
Date Deposited: 22 May 2015 10:16
Last Modified: 08 Mar 2017 09:18
URI: http://sro.sussex.ac.uk/id/eprint/54128

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