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Predicting pKa Values of Quinols and Related Aromatic Compounds with Multiple OH Groups
- Source :
- The Journal of Organic Chemistry. 86:14444-14460
- Publication Year :
- 2021
- Publisher :
- American Chemical Society (ACS), 2021.
-
Abstract
- Quinonoid compounds play central roles as redox-active agents in photosynthesis and respiration and are also promising replacements for inorganic materials currently used in batteries. To design new quinonoid compounds and predict their state of protonation and redox behavior under various conditions, their pKa values must be known. Methods that can predict the pKa values of simple phenols cannot reliably handle complex analogues in which multiple OH groups are present and may form intramolecular hydrogen bonds. We have therefore developed a straightforward method based on a linear relationship between experimental pKa values and calculated differences in energy between quinols and their deprotonated forms. Simple adjustments allow reliable predictions of pKa values when intramolecular hydrogen bonds are present. Our approach has been validated by showing that predicted and experimental values for over 100 quinols and related compounds differ by an average of only 0.3 units. This accuracy makes it possible to select proper pKa values when experimental data vary, predict the acidity of quinols and related compounds before they are made, and determine the sites and orders of deprotonation in complex structures with multiple OH groups.
- Subjects :
- 010304 chemical physics
Hydrogen bond
Organic Chemistry
Protonation
010402 general chemistry
01 natural sciences
Redox
0104 chemical sciences
chemistry.chemical_compound
Deprotonation
Linear relationship
chemistry
Computational chemistry
Intramolecular force
0103 physical sciences
Inorganic materials
Phenols
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 86
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi...........2c196a2834435b81eedd8398ee9b3a4d