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  1. Theoretical descriptors response to the calculations of the relative pK a values of some boronic acids in aqueous solution: A DFT study
Theoretical descriptors response to the calculations of the relative pK a values of some boronic acids in aqueous solution: A DFT study
581 viewed

Theoretical descriptors response to the calculations of the relative pK a values of some boronic acids in aqueous solution: A DFT study

Kheirjou, S

Theoretical descriptors response to the calculations of the relative pK a values of some boronic acids in aqueous solution: A DFT study

Kheirjou, S ; Sharif University of Technology | 2012

581 Viewed
  1. Type of Document: Article
  2. DOI: 10.1016/j.comptc.2012.08.012
  3. Publisher: 2012
  4. Abstract:
  5. With the specific target of calculating the pK a values of boronic acids (RB(OH) 2) in aqueous solution we inquired the solute-solvent interactions of these acids and their corresponding conjugate base. Relative pK a values were computed for each boronic acid using methylboronic acid (CH 3B(OH) 2) as a reference. All gas phase computations were performed at (MP2/6-311++G(d,p)//B3LYP/6-31+G(d)) level of theory. Solvation was included in the calculations using the polarized continuum model (PCM) at the HF/6-31G(d,p) level. The geometry optimization of studied structures was performed with DFT computation and the optimized structures were used to carry out Natural Bond Orbital (NBO) analysis. Natural Bond Orbital (NBO) analysis was examined as indicator for the variations observed in the calculated pK a. Natural resonance theory (NRT) was used to calculate the natural bond order and predict bond polarity. The NRT results indicate that the O-H bonds in all studied compounds have an electrovalency character. The results revealed that difference in acid strength is more relevant to the type of substituent. The electron withdrawing substituent will increase the acidic strength. However, the electron releasing substituent will have a reverse effect and decrease the acidic strength. There are good agreement between theoretical values and experimental results for this series of compounds, the average error was found to be less than 1.2 pK a unit
  6. Keywords:
  7. Acidity ; Boronic acid ; DFT ; Natural Bond Orbital (NBO) ; Natural resonance theory (NRT)
  8. Source: Computational and Theoretical Chemistry ; Volume 1000 , 2012 , Pages 1-5 ; 2210271X (ISSN)
  9. URL: http://www.sciencedirect.com/science/article/pii/S2210271X12004070