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Hydrophobicity of Long Chain n -Alkyl Carboxylic Acids, as Measured by Their Distribution Between Heptane and Aqueous Solutions

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Smith, Ross, Tanford, Charles·1973·Proceedings of the National Academy of Sciences

Abstract

Previous data for the distribution of the n -alkyl carboxylic acids between aqueous buffers and heptane have suggested that the free energy of transfer between the two solvents does not increase with the length of the alkyl chain beyond palmitic acid, indicating a limit to the hydrophobicity of the alkyl chain at a length of about 15 carbon atoms. It is shown in this paper that previous measurements were influenced by unexpectedly strong pH-dependent association of the long-chain acids in the aqueous phase. Under conditions where such association becomes negligible, the free energy of transfer becomes a strictly linear function of alkyl chain length for all acids up to behenic acid (C 21 H 43 COOH).

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Metadata

Authors
Smith, R., & Tanford, C.
Venue
Proceedings of the National Academy of Sciences
Published
1973-02
Volume
70
Issue
2
Pages
289-293
ISSN
  • 0027-8424 (ISSN-L)
  • 1091-6490
OpenAlex
W2078637473
Cited by
163
References
0
FWCI
8.47
Type
journal article
Language
en
Open access
green

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CoChat. (2026). Citation check: Hydrophobicity of Long Chain n -Alkyl Carboxylic Acids, as Measured by Their Distribution Between Heptane and Aqueous Solutions. https://app.cochat.ai/papers/10.1073/pnas.70.2.289
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Smith, R., & Tanford, C. (1973). Hydrophobicity of Long Chain n -Alkyl Carboxylic Acids, as Measured by Their Distribution Between Heptane and Aqueous Solutions. Proceedings of the National Academy of Sciences. https://doi.org/10.1073/pnas.70.2.289

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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.