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Theoretical Study of O-CH3 Bond Dissociation Enthalpy in Anisole Systems.


ABSTRACT: Understanding ubiquitous methyl transfer reactions requires a systematic study of thermodynamical parameters that could reveal valuable information about the nature of the chemical bond and the feasibility of those processes. In the present study, the O-CH3 bond dissociation enthalpies (BDEs) of 67 compounds belonging to phenol/anisole systems were calculated employing the Gaussian-4 (G4) method. Those compounds contain different substituents including alkyl groups, electron-donating groups (EDGs), and electron-withdrawing groups (EWGs). The results show that the bigger branched alkyl groups and EDGs will destabilize the O-CH3 bond, while EWGs have the opposite effect. A combination of different effects including steric effects, hydrogen bonds, and substituents and their position can achieve around 20 kcal/mol difference compared to the basic phenyl frame. Also, the linear correlation between σp + and O-CH3 BDE can provide a reference for the O-CH3 BDE prediction. The present study represents a step forward to establish a comprehensive O-CH3 BDE database to understand the substituent effect and make its contribution to the rational design of inhibitors and drugs.

SUBMITTER: Li R 

PROVIDER: S-EPMC8412933 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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Theoretical Study of O-CH<sub>3</sub> Bond Dissociation Enthalpy in Anisole Systems.

Li Rui R   Du Tianshu T   Liu Jingxing J   Aquino Adelia J A AJA   Zhang Jianyu J  

ACS omega 20210819 34


Understanding ubiquitous methyl transfer reactions requires a systematic study of thermodynamical parameters that could reveal valuable information about the nature of the chemical bond and the feasibility of those processes. In the present study, the O-CH<sub>3</sub> bond dissociation enthalpies (BDEs) of 67 compounds belonging to phenol/anisole systems were calculated employing the Gaussian-4 (G4) method. Those compounds contain different substituents including alkyl groups, electron-donating  ...[more]

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