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Single-centered hydrogen-bonded enhanced acidity (SHEA) acids: a new class of Bronsted acids

Tian, Z ; Sharif University of Technology | 2009

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  1. Type of Document: Article
  2. DOI: 10.1021/ja9075106
  3. Publisher: 2009
  4. Abstract:
  5. Hydrogen bonds are the dominant motif for organizing the three-dimensional structures of biomolecules such as carbohydrates, nucleic acids, and proteins, and serve as templates for proton transfer reactions. Computations, gas-phase acidity measurements, and pKa determinations in dimethyl sulfoxide on a series of polyols indicate that multiple hydrogen bonds to a single charged center lead to greatly enhanced acidities. A new class of Brønsted acids, consequently, is proposed. © 2009 American Chemical Society
  6. Keywords:
  7. Enhanced acidity ; Gas-phase acidities ; Polyols ; Proton transfer reactions ; Three-dimensional structure ; Binding sites ; Carbohydrates ; Charge transfer ; Dimethyl sulfoxide ; Hydrogen ; Lead ; Nucleic acids ; Proton transfer ; Hydrogen bonds ; Alcohol ; Bronsted acid ; Carbohydrate ; Nucleic acid ; Polyol ; Acidity ; Chemical reaction ; Chemical structure ; Hydrogen bond ; pKa ; Proton transport
  8. Source: Journal of the American Chemical Society ; Volume 131, Issue 46 , 2009 , Pages 16984-16988 ; 00027863 (ISSN)
  9. URL: https://pubs.acs.org/doi/10.1021/ja9075106