Related Experiment Video
Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2,6-Dibromo-4-butyl-aniline
1Department of Chemical & Environmental Engineering, Anyang Institute of Technology, Anyang 455000, People's Republic of China.
This study details the crystal structure of a novel organic compound, C(10)H(13)Br(2)N. The research reveals specific intramolecular and intermolecular hydrogen bonding patterns influencing its molecular arrangement in the solid state.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding molecular interactions is crucial in organic chemistry.
- Crystal structure analysis provides insights into intermolecular forces.
Purpose of the Study:
- To elucidate the crystal structure of the compound C(10)H(13)Br(2)N.
- To investigate the presence and nature of hydrogen bonding within the crystal.
Main Methods:
- Single-crystal X-ray diffraction was employed.
- Analysis of atomic coordinates and bond lengths/angles was performed.
Main Results:
- The amino nitrogen atom is nearly coplanar with the benzene ring (r.m.s. deviation 0.004 Å).
- Weak intramolecular N-H⋯Br hydrogen bonds were identified.
- Molecules form zigzag chains via intermolecular N-H⋯N hydrogen bonds along the b-axis.
Conclusions:
- The crystal packing is governed by specific hydrogen bonding interactions.
- The coplanarity of the amino group and benzene ring suggests electronic delocalization.
- The identified hydrogen bonds dictate the compound's solid-state architecture.
Related Concept Videos
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Diazonium Group Substitution: –OH and –H
Radical Substitution: Allylic Bromination
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene
Nomenclature of Aryl and Heterocyclic Amines
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

