Comment on "The role of electrostatic induction in secondary isotope effects on acidity" by E. A. Halevi, New J. Chem., 2014, 38, 3840
- Author(s): Perrin, CL
- et al.
Published Web Locationhttps://doi.org/10.1039/c4nj01887g
We reaffirm our conclusion that secondary deuterium isotope effects on acidity are due to n-σ∗ delocalization that decreases vibrational frequencies and zero-point energies. We reject an electrostatic or inductive explanation that arises from the anharmonicity of the C-H bond. We address calculated values of atomic charges, dipole moments, and dipole-moment derivatives dμ/dr, and we show the isotope effect to be a stereoelectronic phenomenon arising from harmonic vibrations.