ArticleThe journal of physical chemistry. A2009
Estimation of molecular acidity via electrostatic potential at the nucleus and valence natural atomic orbitals.
Article in The journal of physical chemistry. A, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 130 citations in OpenAlex.
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- Revealing the Chemical Nature of Functional Groups on Graphene Oxide by Integrating Potentiometric Titration and Ab Initio Calculations.ACS omega · 2023Article
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- Baird's Rule in Substituted Fulvene Derivatives: An Information-Theoretic Study on Triplet-State Aromaticity and Antiaromaticity.ACS omega · 2018Article
- On the physical interpretation of the nuclear molecular orbital energy.The Journal of chemical physics · 2017Article
- Prediction of the Fate of Organic Compounds in the Environment From Their Molecular Properties: A Review.Critical reviews in environmental science and technology · 2015Article
- A theoretical study on the gas-phase protonation of pyridine and phosphinine derivatives.Journal of molecular modeling · 2013Article
- Protophilicity index and protofelicity equalization principle: new measures of Brønsted-Lowry-Lewis acid-base interactions.Journal of molecular modeling · 2013Article
- Lee Pedersen's work in theoretical and computational chemistry and biochemistry.World journal of biological chemistry · 2011Article
- Steric, quantum, and electrostatic effects on S(N)2 reaction barriers in gas phase.The journal of physical chemistry. A · 2010Article
- Theoretical and experimental studies of the isomeric protonation in solution for a prototype aliphatic ring containing two nitrogens.The journal of physical chemistry. B · 2010Article
- Molecular acidity: A quantitative conceptual density functional theory description.The Journal of chemical physics · 2009Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
An effective approach of estimating molecular pK(a) values from simple density functional calculations is proposed in this work. Both the molecular electrostatic potential (MEP) at the nucleus of the acidic atom and the sum of valence natural atomic orbitals are employed for three categories of compounds, amines and anilines, carbonyl acids and alcohols, and sulfonic acids and thiols. A strong correlation between experimental pK(a) values and each of these two quantities for each of the three categories has been discovered. Moreover, if the MEP is subtracted by the isolated atomic MEP for each category of compounds, we observe a single unique linear relationship between the resultant MEP difference and experimental pK(a) data of amines, anilines, carbonyl acids, alcohols, sulfonic acids, thiols, and their substituents. These results can generally be utilized to simultaneously estimate pK(a) values at multiple sites with a single calculation for either relatively small molecules in drug design or amino acids in proteins and macromolecules.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.