Related Experiment Video
Updated: Aug 9, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2,4-Dibromo-3-methoxy-6-nitrobenzaldeyde: effect of substituents on ring geometry
Paixao1, Matos Beja A, Ramos Silva M
1Departamento de Fisica, Faculdade de Ciencias e Tecnologia, Universidade de Coimbra, P-3004-516 Coimbra, Portugal. jap@pollux. fis.uc.pt.
Abstract:
In the title compound, C(8)H(5)Br(2)NO(4), the endocyclic angles of the ring deviate significantly from the ideal value of 120 degrees. The substituents deviate from the plane of the ring, with large twist angles for the aldehyde, nitro and methoxy groups. The geometry of the molecule in the crystal is compared with that of the isolated molecule, as given by a self-consistent field molecular-orbital Hartree-Fock calculation. Only weak hydrogen bonds of the C-H.Br and C-H.O types are present in the crystal structure.
Related Concept Videos
Directing Effect of Substituents: ortho–para-Directing Groups
Directing Effect of Substituents: meta-Directing Groups
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
Directing and Steric Effects in Disubstituted Benzene Derivatives
Nomenclature of Aromatic Compounds with Multiple Substituents
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...

