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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...
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
VSEPR Theory and the Effect of Lone Pairs04:01

VSEPR Theory and the Effect of Lone Pairs

Effect of Lone Pairs of Electrons on Molecule Geometry
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
Other Nuclides: 31P, 19F, 15N NMR01:16

Other Nuclides: 31P, 19F, 15N NMR

Many organic, inorganic, and biological molecules contain spin-half nuclei such as nitrogen-15, fluorine-19, and phosphorus-31. As a result, NMR studies of these nuclei have found extensive applications in chemical and biological research.
While fluorine-19 and phosphorous-31 have high natural abundances (100%) and positive gyromagnetic ratios, nitrogen-15 has a low natural abundance and a negative gyromagnetic ratio. However, nitrogen-15 is still preferred over nitrogen-14 (which has a high...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

Published on: September 26, 2016

Two polymorphs of N-(2,6-difluorophenyl)formamide.

Bernard Omondi1, Demetrius C Levendis, Marcus Layh

  • 1Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits, 2050 Johannesburg, South Africa. bernardowaga@gmail.com

Acta Crystallographica. Section C, Crystal Structure Communications
|September 4, 2009
PubMed
Summary

Two crystal forms of N-(2,6-difluorophenyl)formamide exhibit distinct structures and packing arrangements. Differences in hydrogen bonding and space groups (Pbca and P2(1)) highlight polymorphism in this compound.

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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Materials science

Background:

  • Polymorphism is crucial in determining the physical and chemical properties of organic compounds.
  • Understanding crystal structures aids in predicting material behavior and optimizing synthesis.
  • N-(2,6-difluorophenyl)formamide is a compound with potential applications where solid-state properties are critical.

Purpose of the Study:

  • To elucidate the distinct crystal structures of two polymorphic forms of N-(2,6-difluorophenyl)formamide.
  • To analyze the differences in molecular geometry, space groups, and packing arrangements between the polymorphs.
  • To investigate intermolecular interactions, including hydrogen bonding and weaker forces, contributing to crystal stability.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic arrangement of each polymorph.
  • Crystallographic data were collected under varying crystallization conditions to isolate distinct forms.
  • Computational methods were utilized to analyze contributing interactions like pi-pi stacking and C-H...F bonds.

Main Results:

  • Two distinct polymorphic forms, designated (Ia) and (Ib), were identified, crystallizing in orthorhombic Pbca and monoclinic P2(1) space groups, respectively.
  • Both polymorphs feature a trans conformation with the formamide group deviating from the aromatic ring plane.
  • Form (Ia) exhibits an alternating molecular stacking with N-H...O hydrogen bonds along the a-axis, while form (Ib) shows linear stacking of hydrogen-bonded molecules.

Conclusions:

  • The study successfully characterized two unique crystal structures of N-(2,6-difluorophenyl)formamide, revealing significant differences in their solid-state arrangements.
  • The observed polymorphism is driven by variations in crystal packing and hydrogen bonding patterns.
  • The findings provide valuable insights into the structure-property relationships of this compound and contribute to the broader understanding of organic crystal engineering.