Acidity enhancement of α‐carbon of beta diketones via hydroxyl substituents: A density functional theory study. (2nd December 2020)

• Record Type: Journal Article
• Authors: Rahimi, Mona; Fattahi, Alireza
• Is Part Of: Journal of physical organic chemistry. Volume 34:Number 3(2021)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2020-12-02
• Subjects: acidity enhancement -- AIM -- beta diketones -- DFT -- NBO; Chemistry, Physical organic -- Periodicals; 547.1
• DOI: 10.1002/poc.4157
• Languages: English
• ISSNs: 0894-3230

Abstract

Abstract: Density functional theory method and B3LYP/6‐311++G(d, p) level of theory were used to determine the acidity of α‐carbon in the hydroxyl derivatives of beta diketones in the gas phase. An investigation of acidity strength in the gas phase indicates that α‐carbon of hydroxyl derivatives of beta diketones become stronger acids than the α‐carbon of beta diketone itself as their conjugate bases gain more stability via both enolate and hydrogen bond formation. Natural bond orbital and quantum theory of atoms in molecules analyses also confirm the role of hydrogen bond interactions on increasing the acidity of α‐carbon of hydroxyl derivatives of beta diketones. Abstract : ‐α‐carbon of hydroxyl derivatives of beta diketones become stronger acids than the α‐carbon of beta diketone itself as their conjugate bases gain more stability via both enolate and hydrogen bond formation.