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Related Concept Videos

Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

12.1K
Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
12.1K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

12.1K
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...
12.1K
Cycloalkanes02:28

Cycloalkanes

14.1K
Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
14.1K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

2.3K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
2.3K
Polymer Classification: Crystallinity01:21

Polymer Classification: Crystallinity

3.1K
Unlike ionic or small covalent molecules, polymers do not form crystalline solids due to the diffusion limitations of their long-chain structures. However, polymers contain microscopic crystalline domains separated by amorphous domains.
Crystalline domains are the regions where polymer chains are aligned in an orderly manner and held together in proximity by intermolecular forces. For example, chains in the crystalline domains of polyethylene and nylon are bound together by van der Waals...
3.1K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

16.0K
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...
16.0K

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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An amide cyclo-phane.

Vijayan Viswanathan1, Ayyavu Thirunarayanan2, Perumal Rajakumar2

  • 1Centre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India.

Acta Crystallographica. Section E, Structure Reports Online
|September 25, 2014
PubMed
Summary

This study details a novel macrocycle, C32H30N4O2S2, featuring a unique bis-(2-mercaptophenyl)isophthalamide and piperazine structure. Its crystal packing reveals intricate hydrogen bonding networks and molecular conformations.

Keywords:
crystal structure

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Crystallography

Background:

  • Macrocyclic compounds are crucial in host-guest chemistry and materials science.
  • The synthesis and structural characterization of novel macrocycles provide insights into molecular design and self-assembly.
  • Bis-aryl isophthalamides and piperazine units are common building blocks in macrocyclic synthesis.

Purpose of the Study:

  • To synthesize and characterize a novel macrocyclic compound, 8,18-dithia-2,6-diaza-13(1,4)-piperidina-1(1,2),4(1,3),7(1,2)-tribenzenaoctadecaphane-10,15-diyne-3,6-dione (C32H30N4O2S2).
  • To elucidate the molecular structure, conformation, and crystal packing of the synthesized macrocycle using X-ray diffraction.
  • To investigate the role of intra- and intermolecular hydrogen bonding in the self-assembly of the macrocycle in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional structure of the title compound.
  • Analysis of bond lengths, bond angles, and dihedral angles to describe the molecular geometry and conformation.
  • Identification and analysis of intra- and intermolecular hydrogen bonding interactions (N-H⋯S, C-H⋯S, C-H⋯O) and their contribution to crystal packing.

Main Results:

  • The synthesized macrocycle, C32H30N4O2S2, features a bis-(2-mercaptophenyl)isophthalamide unit linked to a 1,4-di(but-2-yn-1-yl)piperazine unit, forming a macrocyclic structure.
  • The isophthalamide ring system exhibits specific inclinations relative to the mercaptophenyl rings and to each other, indicating a non-planar overall geometry.
  • The piperazine ring adopts a chair conformation, and the crystal structure is stabilized by two intramolecular N-H⋯S hydrogen bonds and intermolecular C-H⋯S and C-H⋯O hydrogen bonds, forming layered structures.

Conclusions:

  • The study successfully synthesized and structurally characterized a novel macrocycle with potential applications in supramolecular chemistry.
  • The detailed crystallographic analysis reveals the conformational preferences and the significant role of hydrogen bonding in organizing the molecules in the solid state.
  • The observed molecular arrangement and hydrogen bonding patterns provide valuable insights for the design of new macrocyclic architectures with tailored properties.