Related Experiment Video
Updated: Jun 5, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2,6-Diisopropyl-anilinium chloride
1Pharmaceutical Sciences, Pfizer Global R&D, Eastern Point Road, Groton, CT 06340, USA.
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
This study details the crystal structure of a novel organic compound, revealing an unusual twist in an isopropyl group due to a specific short-range interaction. This finding offers insights into molecular geometry and intermolecular forces.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding the three-dimensional arrangement of atoms in crystalline organic compounds is crucial for predicting their physical and chemical properties.
- Intermolecular interactions, such as hydrogen bonding and van der Waals forces, play a significant role in dictating crystal packing and molecular conformation.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(12)H(20)N(+)·Cl(-).
- To investigate the geometrical features and intermolecular interactions influencing the conformation of isopropyl groups within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and torsion angles to characterize molecular geometry.
- Identification and analysis of hydrogen bonding and other short-range contacts.
Main Results:
- The crystal structure features chloride anions on twofold axes and the cation in a general position.
- A hydrogen-bonded ladder motif was observed along the c axis, utilizing all conventional hydrogen bond donors and acceptors.
- Unusual torsion angles were found between aromatic systems and isopropyl groups, with one isopropyl group exhibiting a twist likely caused by a short Cl⋯HC(methine) contact (2.88 Å).
Conclusions:
- The crystal structure of C(12)H(20)N(+)·Cl(-) has been determined, highlighting specific packing arrangements and intermolecular interactions.
- A short Cl⋯HC(methine) contact is identified as the probable cause for an atypical twisted conformation in one of the isopropyl groups.
- This study provides valuable insights into the subtle interplay between intermolecular forces and molecular geometry in organic crystals.
Related Concept Videos
02:45Alkyl Halides
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
01:07Preparation of Acid Anhydrides
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
01:07Acid Halides to Amides: Aminolysis
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
01:19Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
02:46Halogenation of Alkenes
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
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.
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.
01:20Anionic Chain-Growth Polymerization: Overview
The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...