Prediction of the standard potentials for one-electron oxidation of N,N,N′,N′ tetrasubstituted p-phenylenediamines by calculation

Literature Information

Publication Date 2021-09-02
DOI 10.1039/D1CP02315B
Impact Factor 3.676
Authors

Cecilie L. Andersen, Evanildo G. Lacerda, Jr, Jørn B. Christensen, Stephan P. A. Sauer, Ole Hammerich


View Original

Abstract

The formal potentials for the reversible one-electron oxidation of N,N,N′,N′ tetrasubstituted p-phenylenediamines in acetonitrile have been applied as a test set for benchmarking computational methods for a series of compounds with only small structural differences. The aim of the study is to propose a simple method for calculating the standard oxidation potentials, and therefore, the protocol is progressively developed by adding more terms in the energy expression. In addition, the effect of including implicit solvation models (IEFPCM, CPCM, and SMD), larger basis sets, and correlation methods are investigated. The oxidation potentials calculated using the G3MP2B3 approach with IEFPCM resulted in the best fit (R2 = 0.9624), but the slope of the correlation line, 0.74, is far from the optimal value, 1.00. B3LYP/6-311++G(d,p) and TPSSh/6-311++G(2d,p) yielded only slightly less consistent data (R2 = 0.9388 and R2 = 0.9425), but with much better slopes, 1.00 and 0.94, respectively. We conclude that it is important to investigate the basis set size and treatment of electron correlation when calculating oxidation potentials for N,N,N′,N′ tetrasubstituted p-phenylenediamines.

Related Literature

Long-lived coherent oscillations of the femtosecond transients in cyanobacterial photosystem I

Oleg M. Sarkisov, Fedor E. Gostev, Vladimir I. Novoderezhkin, Oxana A. Gopta, Mahir D. Mamedov, Alexey Yu. Semenov

2006-11-13 Paper

DOI: 10.1039/B605660A

Weak distance dependence of through-bond interactions in tetrahydro-4H-thiopyran-4-ylidene end-capped oligo(cyclohexylidenes); a computational survey

Cornelis A. van Walree, Alwin W. Marsman, Joop H. van Lenthe, Leonardus W. Jenneskens

2007-01-26 Paper

DOI: 10.1039/B616893K

Infrared spectroscopy and structure of photochemically protonated biomolecules in the gas phase: a noradrenaline analogue, lysine and alanyl alanine

Timothy D. Vaden, Tjalling S. J. A. de Boer, Neil A. MacLeod, Elaine M. Marzluff, John P. Simons, Lavina C. Snoek

2007-03-27 Paper

DOI: 10.1039/B700805H

Inelastic insights for molecular tunneling pathways: Bypassing the terminal groups

Alessandro Troisi, Mark A. Ratner

2007-03-21 Paper

DOI: 10.1039/B702377D

pH-responsive self-assembly of carboxyl-terminated hyperbranched polymers

Wenyong Dong, Yongfeng Zhou, Deyue Yan, Huiqin Li, Yu Liu

2007-01-23 Paper

DOI: 10.1039/B615525C

Structural and redox properties of VOx and Pd/VOx thin film model catalysts studied by TEM and SAED

Simon Penner, Bernhard Klötzer, Bernd Jenewein

2007-03-19 Paper

DOI: 10.1039/B700650K

Back matter

Front/Back Matter

DOI: 10.1039/B705465N

Formation of mesoscopic water networks in aqueous systems

Lívia B. Pártay, Pál Jedlovszky, Ivan Brovchenko, Alla Oleinikova

2007-01-25 Paper

DOI: 10.1039/B617042K

You might also like

Compound Q&A

What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?

N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...

52818-63-0N-(4-Methoxybenzyl)-...
Compound Q&A

What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?

When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...

1050507-06-6Ethyl 4-(2-chlorophe...
Compound Q&A

What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?

Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...

628-39-7Diethyldiselane
Compound Q&A

What is the market or research trend for oxocopper (CAS: 12053-18-8)?

The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...

12053-18-8oxocopper; oxo-(oxoc...
Compound Q&A

What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?

The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...

1268519-54-55-{[(2-Methyl-2-prop...
Compound Q&A

What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?

2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...

35981-63-62-(1-Pyrrolidinyl)-4...
Compound Q&A

What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?

2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...

91556-75-12-(3-Pyridinyl)-1-az...
Compound Q&A

How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?

(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...

129704-91-2(S)-Alpha-allyl-prol...
Compound Q&A

What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?

3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...

4857-42-53-Methyl-1,2-oxazole...
Compound Q&A

How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?

Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...

1281816-04-3Lys-SMCC-DM1

Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.