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Cooperativity effects of intramolecular OH...O interactions on pK a values of polyolalkyl sulfonic acids in the gas phase and solution: A density functional theory study

Najdian, A ; Sharif University of Technology

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  1. Type of Document: Article
  2. DOI: 10.1002/poc.3307
  3. Abstract:
  4. Density functional theory method and B3LYP/6-311++G(d,p) level of theory were used to determine the acidity of alkyl sulfonic acids and polyolalkyl sulfonic acids in the gas and solution (H2O, DMSO, and CH 3CN) phase. Polarized continuum model was applied to calculate pKa values of alkyl sulfonic acids and polyolalkyl sulfonic acids. A comparison between acidity of alkyl sulfonic acids and polyolalkyl sulfonic acids in the gas and solution phase indicates that the acidity strength of polyolalkyl sulfonic acids enhances with the increase of the cooperativity effect of intramolecular hydrogen bonds in polyolalkyl sulfonic acids. Natural bond orbital and quantum theory of atoms in molecules analyses also confirm the role of cooperativity effect on the acidity of polyolalkyl sulfonic acids
  5. Keywords:
  6. Hydrogen bonding ; Continuum mechanics ; Density functional theory ; Quantum theory ; Alkyl sulfonic acid ; Cooperativity ; NBO analysis ; QTAIM analysis ; Hydrogen bonds
  7. Source: Journal of Physical Organic Chemistry ; Vol. 27, issue. 7 , 2014 , p. 604-612
  8. URL: http://onlinelibrary.wiley.com/doi/10.1002/poc.3307/abstract