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Bulk solution data have been collected for stearic acid in cyclohexane and in toluene to quantify the extent of self-association of the acid in terms of the dimer self-dissociation constant, Kd. Composition and temperature-dependent experimental data have been collected to determine Kd, the enthalpy of dissociation, and temperature-dependent infrared molar absorption coefficients. The interaction of stearic acid with small amounts of water present in non-aqueous solvents is also addressed and quantified with a hetero-dissociation (or dehydration) constant, Kh. Existing data for acetic acid are also considered. The model connects Kd and Kh to the vapor-phase association equilibria. Solute dipole\u2013solvent quadrupole interactions are shown to have a major effect on Kd in quadrupolar liquids, such as toluene, benzene, and CS2. This work provides important background as a prelude to adsorption studies of these additives from non-aqueous solvents to solid surfaces with relevance to commercial fluids, such as oil-based corrosion inhibitors and friction modifiers. Moreover, the presented theory of the solvent effect on Kd is a first step to generalization of standard implicit solvent models in computational chemistry (such as the polarizable continuum model) to media of significant quadrupolar strength. This is expected to be particularly important for polar species dissolved in CO2 relevant for carbon capture and storage where appropriate models do not currently exist.<\/jats:p>","DOI":"10.1063\/5.0137052","type":"journal-article","created":{"date-parts":[[2023,6,5]],"date-time":"2023-06-05T06:18:26Z","timestamp":1685945906000},"update-policy":"https:\/\/doi.org\/10.1063\/aip-crossmark-policy-page","source":"Crossref","is-referenced-by-count":10,"title":["Effect of the solvent quadrupolarizability on the strength of the hydrogen bond: Theory vs data for the Gibbs energy and enthalpy of homo- and heteroassociation between carboxylic acids and water"],"prefix":"10.1063","volume":"158","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5199-4290","authenticated-orcid":false,"given":"Lana J.","family":"Farren","sequence":"first","affiliation":[{"name":"Institute for Energy and Environmental Flows and Department of Chemistry, University of Cambridge 1 , Cambridge CB3 0EZ, United Kingdom"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4157-097X","authenticated-orcid":false,"given":"Najib","family":"Sharifi","sequence":"additional","affiliation":[{"name":"Institute for Energy and Environmental Flows and Department of Chemistry, University of Cambridge 1 , Cambridge CB3 0EZ, United Kingdom"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5224-2368","authenticated-orcid":false,"given":"Stuart M.","family":"Clarke","sequence":"additional","affiliation":[{"name":"Institute for Energy and Environmental Flows and Department of Chemistry, University of Cambridge 1 , Cambridge CB3 0EZ, United Kingdom"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4639-1225","authenticated-orcid":false,"given":"Radomir I.","family":"Slavchov","sequence":"additional","affiliation":[{"name":"School of Engineering and Materials Science, Queen Mary University of London 2 , London E1 4NS, United Kingdom"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"317","published-online":{"date-parts":[[2023,6,5]]},"reference":[{"key":"2023081121393180000_c1","volume-title":"Solvents and Solvent Effects in Organic Chemistry","year":"2002"},{"key":"2023081121393180000_c2","volume-title":"Physical Chemistry of Electrolyte Solutions","year":"1998"},{"key":"2023081121393180000_c3","doi-asserted-by":"publisher","first-page":"1486","DOI":"10.1021\/ja01299a050","article-title":"Electric moments of molecules in liquids","volume":"58","year":"1936","journal-title":"J. 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