Related Experiment Video
Updated: Jul 19, 2026
06:35
Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Four substituted benzohydrazides: hydrogen-bonded structures in one, two and three dimensions
Solange M S V Wardell1, Thatyana R A Vasconcelos, Marcus V N de Souza
1Instituto de Tecnologia em Fármacos, Far-Manguinhos, FIOCRUZ, 21041-250 Rio de Janeiro, RJ, Brazil.
Acta Crystallographica. Section C, Crystal Structure Communications
|September 30, 2006
Summary
Different dichlorobenzohydrazide isomers exhibit unique hydrogen bonding patterns, forming chains, sheets, or 3D frameworks. These structural variations influence molecular assembly in crystalline solids.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Hydrogen bonding is a critical intermolecular force dictating crystal structures.
- Benzohydrazide derivatives are important organic compounds with diverse applications.
- Understanding crystal packing is essential for predicting material properties.
Purpose of the Study:
- To investigate the crystal structures of various substituted benzohydrazides.
- To elucidate the role of hydrogen bonding in the self-assembly of these molecules.
- To compare the supramolecular architectures formed by different isomers.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed.
- Analysis of intermolecular interactions, particularly hydrogen bonds, was performed.
- Comparison of crystal packing motifs for related compounds.
Main Results:
- 2,6-Dichlorobenzohydrazide forms simple 1D chains via N-H...O hydrogen bonds.
- 2,4-Dichlorobenzohydrazide exhibits complex sheet structures with N-H...N and N-H...O bonds.
- 4-Amino-2-chlorobenzohydrazide monohydrate and 2-nitrobenzohydrazide form 3D frameworks through extensive hydrogen bonding.
Conclusions:
- The position and nature of substituents significantly influence the hydrogen bonding networks and resulting crystal architectures.
- Diverse supramolecular structures, from 1D chains to 3D frameworks, can arise from subtle molecular modifications.
- This study highlights the versatility of benzohydrazide derivatives in forming intricate crystalline assemblies.
Related Concept Videos
01:18Structure of Benzene: Molecular Orbital Model
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
01:07Structure of Benzene: Kekulé Model
In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
01:11Nomenclature of Aromatic Compounds with Multiple Substituents
When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
02:52Resonance
The Lewis structure of a nitrite anion (NO2−) may actually be drawn in two different ways, distinguished by the locations of the N-O and N=O bonds.
01:37NMR Spectroscopy of Benzene Derivatives
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
03:24Hybridization of Atomic Orbitals I
The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...