Correlations and predictions of carboxylic acid pKa values using intermolecular structure and properties of hydrogen-bonded complexes

The Journal of Physical Chemistry. a
Li TaoFu-Ming Tao

Abstract

Density functional theory calculations have been preformed on a series of hydrogen-bonded complexes of substituted aliphatic and aromatic carboxylic acids with ammonia. Molecular properties, particularly those related to hydrogen bonding, have been carefully examined for their interdependence as well as dependence on the acidity of the acid. The bond length and stretching frequency of the hydroxyl group and the hydrogen-bond length and energy of the complex are shown to be highly correlated with each other and are linearly correlated with available literature pKa values of the carboxylic acids. The linear correlations resulting from the fit to the available pKa values can be used to predict the pKa values of similar carboxylic acids. The pKa values so predicted using the different molecular properties are highly consistent and in good agreement with the literature values. This study suggests that calculated molecular properties of hydrogen-bonded complexes allow effective and systematic prediction of pKa values for a large range of organic acids using the established linear correlations. This approach is unique in its capability to determine the acidity of a particular functional group or the local acidity within a large molecu...Continue Reading

Citations

Oct 18, 2011·Environmental Science & Technology·Ying-Hong GuanLi-Wei Chen
Aug 4, 2009·Journal of the American Chemical Society·Grant T Rice, M Christina White
Jun 15, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Wei CuiQinghua Lu
Jan 12, 2011·Annual Review of Physical Chemistry·Kenneth R Leopold
Dec 21, 2016·The Journal of Physical Chemistry. a·Sofja TshepelevitshIvo Leito
May 9, 2009·European Journal of Mass Spectrometry·Solveig Gaarn Olesen, Steen Hammerum
Feb 1, 2019·Journal of Molecular Modeling·Niraj VermaElfi Kraka
May 17, 2011·Physical Chemistry Chemical Physics : PCCP·A P Harding, P L A Popelier
Feb 6, 2009·The Journal of Physical Chemistry. B·Sebastijan PeljhanKsenija Kogej
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Osamu HayashidaTakaaki Miyazaki
Jun 18, 2021·Journal of Chemical Information and Modeling·Zeynep Pinar HaslakGerald Monard
Jul 28, 2021·The Journal of Organic Chemistry·Roberta PacificoMauro F A Adamo
Nov 3, 2010·Journal of Chemical Information and Modeling·Haiying YuGerrit Schüürmann
Jan 10, 2014·Environmental Science & Technology·Jingyun FangChii Shang
Jan 30, 2014·The Journal of Physical Chemistry. a·Kevin H WeberFu-Ming Tao
Sep 7, 2021·Physical Chemistry Chemical Physics : PCCP·Alessandro MarianiStefano Passerini

❮ 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.