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Quantitative decomposition of resonance‐assisted hydrogen bond energy in β‐diketones into resonance and hydrogen bonding (π‐ and σ‐) components using molecular tailoring and function‐based approaches
Author(s) -
Afonin Andrei V.,
Vashchenko Alexander V.
Publication year - 2020
Publication title -
journal of computational chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.907
H-Index - 188
eISSN - 1096-987X
pISSN - 0192-8651
DOI - 10.1002/jcc.26175
Subject(s) - resonance (particle physics) , hydrogen bond , chemistry , hydrogen , component (thermodynamics) , bond energy , molecule , computational chemistry , atomic physics , organic chemistry , thermodynamics , physics
Using the molecular tailoring and function‐based approaches allows one to divide the energy of the O─H⋯O═C resonance‐assisted hydrogen bond in a series of the β‐diketones into resonance and hydrogen bonding components. The magnitude of the resonance component is assessed as about 6 kcal mol −1 . This value increases by ca. 1 kcal mol −1 on going from the weak to strong resonance‐assisted hydrogen bonding. The magnitude of the hydrogen bonding component varies in the wide range from 2 to 20 kcal mol −1 depending on the structure of the β‐diketone in question.