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Related Concept Videos

NMR Spectroscopy of Benzene Derivatives01:37

NMR 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...
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).
Structure of Benzene: Kekulé Model01:07

Structure 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.
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as annulenes. In...
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...
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).

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Related Experiment Video

Updated: Jun 25, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
07:06

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

Amide-pi interactions between formamide and benzene.

Yumi N Imai1, Yoshihisa Inoue, Isao Nakanishi

  • 1Department of Theoretical Drug Design, Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. Imai_Yumi@takeda.co.jp

Journal of Computational Chemistry
|March 6, 2009
PubMed
Summary
This summary is machine-generated.

The study reveals that the NH/pi geometry is the most favorable for amide-pi interactions, with an energy of -3.75 kcal/mol. Other geometries, like C=O/pi, show weaker interactions but can be stabilized by additional molecular contacts.

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Area of Science:

  • Computational Chemistry
  • Molecular Interactions
  • Quantum Chemistry

Background:

  • Amide-pi interactions are crucial in various chemical and biological systems.
  • Understanding these interactions requires accurate theoretical calculations.
  • Previous studies have explored similar non-covalent interactions.

Purpose of the Study:

  • To quantitatively evaluate the strength of amide-pi interactions using high-level ab initio calculations.
  • To identify the most stable geometric configurations for amide-pi interactions.
  • To elucidate the energetic contributions of different atomic arrangements.

Main Methods:

  • High-level ab initio calculations were performed on a formamide-benzene model system.
  • Coupled-Cluster Singles Doubles with Perturbation Theory (CCSD(T)) and Hartree-Fock (HF) methods were employed.
  • Potential Energy Surface (PES) scans were utilized to find minimum energy geometries.
  • Interaction energies were calculated at the complete basis set limit.

Main Results:

  • The NH/pi face-on geometry exhibited the strongest interaction, with an energy of -3.75 kcal/mol.
  • A stacked N/Center geometry showed a significant interaction energy of -2.08 kcal/mol.
  • The C=O/pi geometry displayed a weak, repulsive interaction (<1 kcal/mol) at its minimum energy configuration.

Conclusions:

  • The NH/pi interaction is the dominant attractive force in amide-pi systems.
  • The C=O/pi interaction, while initially weak, can become favorable with cooperative effects from other molecular groups.
  • These findings provide valuable insights into the nature of non-covalent interactions in molecular recognition and design.