The Effect of Intramolecular Hydrogen Bond Type on the Gas-Phase Deprotonation of ortho-Substituted Benzenesulfonic Acids. A Density Functional Theory Study.

ABSTRACT: Structural factors have been identified that determine the gas-phase acidity of ortho-substituted benzenesulfonic acid, 2-XC6H4-SO3H, (X = -SO3H, -COOH, -NO2, -SO2F, -C≡N, -NH2, -CH3, -OCH3, -N(CH3)2, -OH). The DFT/B3LYP/cc-pVTZ method was used to perform conformational analysis and study the structural features of the molecular and deprotonated forms of these compounds. It has been shown that many of the conformers may contain anintramolecular hydrogen bond (IHB) between the sulfonic group and the substituent, and the sulfonic group can be an IHB donor or an acceptor. The Gibbs energies of gas-phase deprotonation ΔrG0298 (kJ mol-1) were calculated for all compounds. It has been set that in ortho-substituted benzenesulfonic acids, the formation of various types of IHB is possible, having a

SUBMITTER: Giricheva NI 

PROVIDER: S-EPMC7764180 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature