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Related Concept Videos

Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...
Intrinsically Disordered Proteins02:18

Intrinsically Disordered Proteins

Intrinsically disordered proteins are a group of proteins that do not fold into specific three-dimensional structures. Their structural flexibility allows them to complement ordered proteins to perform functions that are inaccessible to rigid structures. They are more common in eukaryotes than prokaryotes and may either be exclusively intrinsically disordered or hybrid proteins, consisting of a mix of ordered and disordered regions. The absence of a rigid structure in these proteins can be...
Amyloid Fibrils03:03

Amyloid Fibrils

Amyloid fibrils are aggregates of misfolded proteins.  Under most circumstances, misfolded proteins are either refolded by chaperone proteins or degraded by the proteasome. However, in the case of a mutation or a disease, these proteins can accumulate to form large clusters and often further assemble to form elongated fibers, called fibrils. 
Amyloid deposits were observed as early as 1639 in the liver and the spleen.   In 1854, Rudolph Virchow performed iodine staining, normally used to...

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Related Experiment Video

Updated: Jul 12, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Amitriptylinium picrate: conformational disorder.

S Bindya1, Wing-Tak Wong, M A Ashok

  • 1Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India.

Acta Crystallographica. Section C, Crystal Structure Communications
|September 1, 2007
PubMed
Summary

The crystal structure of amitriptyline picrate reveals conformational disorder and unique intermolecular interactions. These interactions, including hydrogen bonds and pi-pi stacking, lead to the formation of complex molecular clusters and linear arrays.

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PCR Mutagenesis, Cloning, Expression, Fast Protein Purification Protocols and Crystallization of the Wild Type and Mutant Forms of Tryptophan Synthase
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X-Ray Crystallography to Study the Oligomeric State Transition of the Thermotoga maritima M42 Aminopeptidase TmPep1050
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X-Ray Crystallography to Study the Oligomeric State Transition of the Thermotoga maritima M42 Aminopeptidase TmPep1050

Published on: May 13, 2020

Area of Science:

  • Crystallography
  • Structural Chemistry
  • Medicinal Chemistry

Background:

  • Amitriptyline is a tricyclic antidepressant.
  • Picrate is a common counterion used in salt formation.
  • Understanding the solid-state structure of drug salts is crucial for formulation and stability.

Purpose of the Study:

  • To elucidate the crystal structure of the amitriptyline picrate salt.
  • To investigate the intermolecular interactions governing the solid-state assembly of amitriptyline and picrate ions.
  • To characterize the conformational properties of the amitriptyline molecule in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction analysis was performed.
  • The crystal structure was solved and refined.
  • Intermolecular interactions were analyzed using crystallographic tools.

Main Results:

  • The structure exhibits conformational disorder in the dimethylaminopropyl side chain.
  • The central cycloheptadiene ring adopts a bent conformation, resulting in a butterfly shape.
  • Intermolecular C-H...O hydrogen bonds and N-H...O salt bridges form a hetero-tetramer between amitriptyline and picrate.
  • Intermolecular C-H...pi interactions lead to amitriptyline homo-dimers.
  • Pi-pi stacking interactions between aromatic rings contribute to linear arrays.

Conclusions:

  • The crystal structure of amitriptyline picrate reveals complex self-assembly driven by multiple non-covalent interactions.
  • Conformational flexibility and specific intermolecular forces dictate the packing arrangement in the solid state.
  • These findings provide insights into the solid-state behavior of tricyclic antidepressants and their salts.