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Related Concept Videos

Hydrogen Bonds00:26

Hydrogen Bonds

Hydrogen BondsHydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.Hydrogen Bonds Control the World!Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are...
Hybridization of Atomic Orbitals I03:24

Hybridization 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...
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

sp3d and sp3d 2 Hybridization
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
Structure of Benzene: Molecular Orbital Model01:18

Structure 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).
Hydrogen Bonds01:04

Hydrogen Bonds

A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...

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Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
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Published on: October 3, 2014

Hydrogen-bonded network in biphenyl-4,4'-diphosphonic acid.

G Próchniak1, J Zoń, M Daszkiewicz

  • 1Department of Chemistry, Wrocław University of Technology, 27 Wybrzeze Wyspiańskiego Street, 50-370 Wrocław, Poland.

Acta Crystallographica. Section C, Crystal Structure Communications
|July 5, 2007
PubMed
Summary

The crystal structure of biphenyl-4,4′-diphosphonic acid reveals alternating hydrogen-bonded and hydrophobic regions. Strong O-H...O interactions organize molecules, while C-H...pi interactions stabilize aromatic areas.

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Area of Science:

  • Crystal engineering
  • Supramolecular chemistry
  • Materials science

Background:

  • Understanding molecular self-assembly is crucial for designing novel materials.
  • Biphenyl-4,4′-diphosphonic acid (4,4'-bpdp) is a versatile building block for supramolecular structures.
  • The interplay of hydrogen bonding and hydrophobic interactions dictates crystal packing.

Purpose of the Study:

  • To elucidate the crystal structure of biphenyl-4,4′-diphosphonic acid.
  • To investigate the role of different intermolecular interactions in organizing the crystal lattice.
  • To understand the structure-property relationships in phosphonic acid-based materials.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional crystal structure.
  • Analysis of hydrogen bonding (O-H...O) and weak interactions (C-H...pi) was performed.
  • The molecular symmetry and asymmetric unit content were examined.

Main Results:

  • The crystal structure exhibits a unique alternating arrangement of hydrogen-bonded and hydrophobic regions along the a-axis.
  • The biphenyl-4,4′-diphosphonic acid molecule lies on an inversion center, with the asymmetric unit containing half of the molecule.
  • Strong intermolecular O-H...O hydrogen bonds between phosphonic acid groups are the primary drivers of molecular organization.
  • Weak C-H...pi interactions contribute to the stability of the hydrophobic aromatic regions.

Conclusions:

  • The crystal structure of biphenyl-4,4′-diphosphonic acid is characterized by a distinct segregation of polar and non-polar regions.
  • The interplay between strong hydrogen bonding and weaker C-H...pi interactions governs the overall crystal packing and stability.
  • This detailed structural understanding provides insights for the rational design of functional materials based on phosphonic acid derivatives.