1JCH Coupling in Benzaldehyde Derivatives: Ortho Substitution Effect | Zendy

Angelita Nepel | Zendy; Renan V. Viesser | Zendy; Cláudio F. Tormena | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

¹J_CH Coupling in Benzaldehyde Derivatives: Ortho Substitution Effect

Author(s) -

Angelita Nepel,

Renan V. Viesser,

Cláudio F. Tormena

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b03035

Subject(s) - natural bond orbital , benzaldehyde , chemistry , steric effects , fermi contact interaction , coupling constant , atomic orbital , basis set , computational chemistry , coupling (piping) , crystallography , electron , density functional theory , stereochemistry , organic chemistry , materials science , physics , particle physics , metallurgy , catalysis , quantum mechanics

The natural J -coupling (NJC) method is applied to analyze the Fermi contact contribution of the NMR spin-spin coupling constant decomposing this contribution in terms of natural localized molecular orbitals. We investigated the influence of the basis set on the NJC analysis for the formyl group coupling constant ( 1 J CHf ) of benzaldehyde derivatives. NJC and other NBO analyses, like steric and natural Coulombic energy, were chosen to explain the influence of electron-donating and electron-withdrawing groups on 1 J CHf for some substituted benzaldehydes (Me, OH, OMe, F, Cl, Br, I, and NO 2 ). For the ortho derivatives, electronegative substituents near the C-Hf bond increase the 1 J CHf coupling. This effect could be related to an increase in formyl carbon s character and changes in the carbon and hydrogen natural charges. This indicates that the substituents in ortho have a proximity effect on 1 J CHf coupling mainly of electrostatic origin instead of the expected hyperconjugative interactions.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research