Citation: JIANG Xiaoyu, WU Wei, MO Yirong. Strength of Intramolecular Hydrogen Bonds[J]. Acta Physico-Chimica Sinica, ;2018, 34(3): 278-285. doi: 10.3866/PKU.WHXB201708174 shu

Strength of Intramolecular Hydrogen Bonds

JIANG Xiaoyu ¹ ,
WU Wei ² ,
MO Yirong ^3,,

1.
College of Ecological Environment and Urban Construction, Fujian University of Technology, Fuzhou 350108, P. R. China
2.
The State Key Laboratory of Physical Chemistry of Solid Surfaces, iChEM, Fujian Provincial Key Laboratory of Theoretical and Computational Chemistry and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. China
3.
Department of Chemistry, Western Michigan University, Kalamazoo, Michigan 49008, USA

Corresponding author: MO Yirong, yirong.mo@wmich.edu
Received Date: 17 July 2017
Revised Date: 10 August 2017
Accepted Date: 14 August 2017
Available Online: 17 March 2017

The concept of resonance-assisted hydrogen bonds (RAHBs) highlights the synergistic interplay between the π-resonance and hydrogen bonding interactions. This concept has been well-accepted in academia and is widely used in practice. However, it has been argued that the seemingly enhanced intramolecular hydrogen bonding (IMHB) in unsaturated compounds may simply be a result of the constraints imposed by the σ-skeleton framework. Thus, it is crucial to estimate the strength of IMHBs. In this work, we used two approaches to probe the resonance effect and estimate the strength of the IMHBs in the two exemplary cases of the enol forms of acetylacetone and o-hydroxyacetophenone. One approach is the block-localized wavefunction (BLW) method, which is a variant of the ab initio valence bond (VB) theory. Using this approach, it is possible to derive the geometries and energetics with resonance shut down. The other approach is Edmiston's truncated localized molecular orbital (TLMO) technique, which monitors the energy changes by removing the delocalization tails from localized molecular orbitals. The integrated BLW and TLMO studies confirmed that the hydrogen bonding in these two molecules is indeed enhanced by π-resonance, and that this enhancement is not a result of σ constraints.
- Resonance-assisted hydrogen bond,
- Bond strength,
- Valence bond,
- Block-localized wavefunction,
- Truncated localized molecular orbital
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