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Towards a comprehensive hydride donor ability scale.

Markus Horn1, Ludwig H Schappele, Gabriele Lang-Wittkowski

  • 1Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13 (Haus F), 81377 München, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 4, 2012
PubMed
Summary

This study quantifies hydride donor reactivity using benzhydrylium and tritylium ions. A new scale for hydride donor nucleophilicity (N) and sensitivity (s(N)) was developed, spanning over 20 orders of magnitude.

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Area of Science:

  • Organic Chemistry
  • Physical Chemistry

Background:

  • Hydride transfer reactions are fundamental in organic chemistry.
  • Quantifying the nucleophilicity of hydride donors is crucial for understanding reaction mechanisms.

Purpose of the Study:

  • To determine empirical nucleophilicity parameters (N) and sensitivity (s(N)) for various hydride donors.
  • To establish a comprehensive reactivity scale for hydride donors.

Main Methods:

  • Measured rates of hydride transfer from donors to benzhydrylium ions at 20°C.
  • Utilized a linear free energy relationship (log k = s(N)(N+E)) for parameter determination.
  • Compared experimental data with calculations using tritylium ion reactivity.

Main Results:

  • Established empirical nucleophilicity (N) and sensitivity (s(N)) parameters for hydride donors.
  • Demonstrated fair agreement between experimental and calculated rate constants for hydride abstraction by tritylium ions.
  • Constructed a reactivity scale for hydride donors covering over 20 orders of magnitude.

Conclusions:

  • The developed parameters (N and s(N)) provide a robust measure of hydride donor reactivity.
  • The methodology allows for the conversion of existing literature data into a standardized reactivity scale.
  • This work offers a valuable tool for predicting and comparing the reactivity of diverse hydride donors.