ArticleThe journal of physical chemistry. B2007
First-principles calculation of pKa for cocaine, nicotine, neurotransmitters, and anilines in aqueous solution.
Article in The journal of physical chemistry. B, 2007. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 76 citations in OpenAlex.
- Trapping of Nicotinic Acetylcholine Receptor Ligands Assayed byThe Journal of neuroscience : the official journal of the Society for Neuroscience · 2023Article
- Experiment stands corrected: accurate prediction of the aqueous pChemical science · 2019Article
- An Ab Initio Investigation of the 4,4'-Methlylene Diphenyl Diamine (4,4'-MDA) Formation from the Reaction of Aniline with Formaldehyde.Polymers · 2019Article
- Non-canonical Targets Mediating the Action of Drugs of Abuse: Cocaine at the Sigma-1 Receptor as an Example.Frontiers in neuroscience · 2019Article
- Opioid receptor signaling, analgesic and side effects induced by a computationally designed pH-dependent agonist.Scientific reports · 2018Article
- Correlations between theJournal of molecular modeling · 2018Article
- Testing the ability of rhodanine and 2, 4-thiazolidinedione to interact with the human pancreatic alpha-amylase: electron-density descriptors complement molecular docking, QM, and QM/MM dynamics calculations.Journal of molecular modeling · 2017Article
- Origin of pKThe journal of physical chemistry. B · 2017Article
- General Strategy to Introduce pH-Induced Allostery in DNA-Based Receptors to Achieve Controlled Release of Ligands.Nano letters · 2015Article
- Carrier-mediated cocaine transport at the blood-brain barrier as a putative mechanism in addiction liability.The international journal of neuropsychopharmacology · 2014Article
- Modeling of pharmacokinetics of cocaine in human reveals the feasibility for development of enzyme therapies for drugs of abuse.PLoS computational biology · 2012Article
- Catalytic mechanism of cytochrome P450 for 5'-hydroxylation of nicotine: fundamental reaction pathways and stereoselectivity.Journal of the American Chemical Society · 2011Article
- Structural assignment of 6-oxy purine derivatives through computational modeling, synthesis, X-ray diffraction, and spectroscopic analysis.The journal of physical chemistry. B · 2010Article
- Free Energies of Solvation with Surface, Volume, and Local Electrostatic Effects and Atomic Surface Tensions to Represent the First Solvation Shell.Journal of chemical theory and computation · 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
- Comparison of nine programs predicting pK(a) values of pharmaceutical substances.Journal of chemical information and modeling · 2009Article
- First-Principles Determination of Molecular Conformations of Indolizidine (-)-235B' in Solution.Theoretical chemistry accounts · 2009Article
- Estimation of molecular acidity via electrostatic potential at the nucleus and valence natural atomic orbitals.The journal of physical chemistry. A · 2009Article
- An efficient implementation for determining volume polarization in self-consistent reaction field theory.The Journal of chemical physics · 2008Article
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 2 countries.
Funding
Abstract
The absolute pKa values of 24 representative amine compounds, including cocaine, nicotine, 10 neurotransmitters, and 12 anilines, in aqueous solution were calculated by performing first-principles electronic structure calculations that account for the solvent effects using four different solvation models, i.e., the surface and volume polarization for electrostatic interaction (SVPE) model, the standard polarizable continuum model (PCM), the integral equation formalism for the polarizable continuum model (IEFPCM), and the conductor-like screening solvation model (COSMO). Within the examined computational methods, the calculations using the SVPE model lead to the absolute pKa values with the smallest root-mean-square-deviation (rmsd) value (1.18). When the SVPE model was replaced by the PCM, IEFPCM, and COSMO, the rmsd value of the calculated absolute pKa values became 3.21, 2.72, and 3.08, respectively. All types of calculated pKa values linearly correlate with the experimental pKa values very well. With the empirical corrections using the linear correlation relationships, the theoretical pKa values are much closer to the corresponding experimental data and the rmsd values become 0.51-0.83. The smallest rmsd value (0.51) is also associated with the SVPE model. All of the results suggest that the first-principles electronic structure calculations using the SVPE model are a reliable approach to the pKa prediction for the amine compounds.
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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.