Exploring the Inductive Effect through Computational Modeling: A General and Organic Chemistry Lab Experiment

• Valeria A. Stepanova ^[1] ; Joseph K. West ^[2]
  1. [1] Viterbo University

     Viterbo University

     City of La Crosse, Estados Unidos

     
  2. [2] Winona State University

     Winona State University

     City of Winona, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 101, Nº 7, 2024, págs. 2815-2822
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • A straightforward, laptop-friendly computational chemistry laboratory exercise has been developed that facilitates students’ understanding of the inductive effect. Students implement DFT modeling of acetic acid and its methyl and fluoro analogues: trifluoroacetic, fluoroacetic, propanoic, and 2,2-dimethylpropanoic (pivalic) acids, all at a modest level of theory (revPBE/6-31G*). Individually, students complete all computational aspects in ∼45 min using a quad-core laptop computer. Students analyze carbonyl (C═O) vibrational frequencies, C═O bond lengths, and Mulliken charges for the acidic hydrogen in each structure. Students use collected data to compare with literature pKa values to identify trends of chemical properties (i.e., acidity) and electronic effects (i.e., electron-donating and -withdrawing groups).