PMID: 11604215Oct 18, 2001Paper

Thermodynamics of the hydrophobic effect. I. Coupling of aggregation and pK(a) shifts in solutions of aliphatic amines

Biophysical Chemistry
Daumantas Matulis, V A Bloomfield

Abstract

Long aliphatic hydrocarbon chains aggregate in aqueous solution due to the hydrophobic effect, forming structures such as micelles and membranes, while amino groups titrate at basic pH. These two biologically important behaviors are linked in alkylamines, in which the pK(a) of the amino group is shifted downward by aggregation. In this paper we study the thermodynamics of these coupled processes, following aggregation by observing alkylamine pH titration behavior. The magnitude of the shift depended on the aliphatic chain length and on the concentration of alkylamine: longer chains and higher concentrations lowered the pK(a) to a greater extent. Gibbs free energies of protonation and aggregation were calculated from the pK(a) shifts. Enthalpies, entropies, and heat capacities were estimated by van't Hoff analysis from the pK(a) shift dependencies on temperature. However, the results were less precise than the calorimetrically measured values, as described in the following article. A model to calculate titration curves, pK(a) shifts, and aggregation of uncharged alkylamines as a function of aliphatic chain length, concentration, and temperature is presented.

References

May 26, 1995·Science·B Honig, A Nicholls
Jun 6, 1995·Proceedings of the National Academy of Sciences of the United States of America·H NaghibiJ M Sturtevant
Dec 1, 1995·Protein Science : a Publication of the Protein Society·Y Liu, J M Sturtevant
Sep 2, 2000·Biophysical Journal·J J DwyerB García-Moreno E
Feb 28, 1997·Biophysical Chemistry·Y Liu, J M Sturtevant

❮ Previous
Next ❯

Citations

Apr 6, 2006·Proceedings of the National Academy of Sciences of the United States of America·David KisailusDaniel E Morse
Feb 8, 2008·Journal of Biochemical and Biophysical Methods·Lina BaranauskieneDaumantas Matulis
Dec 3, 2014·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·J A RedondoC Elvira
Jul 1, 2006·Applied Spectroscopy·S OlsztynskaN Dupuy
Dec 7, 2017·Physical Chemistry Chemical Physics : PCCP·Ranran TianJingyuan Li
Feb 1, 2014·Chemical Communications : Chem Comm·Geetika Chadha, Yan Zhao
Oct 14, 2018·Nanomaterials·Pedro BurguetePedro Amorós
Mar 30, 2018·Journal of Colloid and Interface Science·Amro S ElhagKeith P Johnston
Nov 14, 2008·Journal of the American Chemical Society·Juan D HenaoHarold H Kung
Aug 1, 2014·Journal of Agricultural and Food Chemistry·Marko VincekovićDarija Jurašin
Jan 25, 2012·The Journal of Physical Chemistry. B·Povilas NorvaišasDaumantas Matulis
Oct 29, 2013·Journal of the American Chemical Society·Dongcui Li, Norman J Wagner
Jan 15, 2014·The Journal of Organic Chemistry·Xiao-Song XueJin-Pei Cheng
Jan 6, 2021·The Journal of Organic Chemistry·Ishani BoseYan Zhao
Aug 22, 2017·Journal of the American Chemical Society·Robert PollicePeter Chen
Apr 19, 2006·Langmuir : the ACS Journal of Surfaces and Colloids·Hye-Young ParkMarc D Porter

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.