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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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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).
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Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

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The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

7.8K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Stereoisomerism of Cyclic Compounds02:33

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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π Molecular Orbitals of 1,3-Butadiene01:24

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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...
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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5- and 6-Membered Rings: A Natural Orbital Functional Study.

Ion Mitxelena1, Juan Felipe Huan Lew-Yee2,3,4, Mario Piris2,5,6

  • 1Fisika Aplikatuko Departamentua, Vitoria-Gasteiz Ingenieritza Eskola, Euskal Herriko Unibertsitatea (EHU), Vitoria-Gasteiz, Euskadi 01006, Spain.

Journal of Chemical Theory and Computation
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Summary
This summary is machine-generated.

The Global Natural Orbital Functional (GNOF) and its variant GNOFm accurately capture electron correlation in molecular rings. These functionals offer a reliable and robust approach for studying dynamic correlation effects in chemistry.

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Area of Science:

  • Computational Chemistry
  • Quantum Chemistry
  • Theoretical Chemistry

Background:

  • Electron correlation is crucial for accurate molecular electronic structure.
  • Existing methods often require approximations like perturbative corrections or active space selections.
  • Dynamic correlation is a key factor in describing molecular systems.

Purpose of the Study:

  • To evaluate the performance of the Global Natural Orbital Functional (GNOF) and its modified version (GNOFm).
  • To assess their ability to capture dynamic correlation effects in molecular rings.
  • To compare GNOF and GNOFm against the benchmark coupled cluster singles doubles with perturbative triples (CCSD(T)) method.

Main Methods:

  • Utilized the Global Natural Orbital Functional (GNOF) and GNOFm.
  • Calculated complete-basis-set limit correlation energies.
  • Employed a set of twelve 5- and 6-membered molecular rings as a reference system.
  • Used Dunning basis sets for calculations.

Main Results:

  • Both GNOF and GNOFm provided a balanced and accurate description of dynamic correlation.
  • GNOFm demonstrated minor but consistent improvements over the original GNOF.
  • The functionals showed robustness and reliability across the tested molecular set.
  • Results were benchmarked against CCSD(T) correlation energies.

Conclusions:

  • The GNOF family of functionals reliably captures dynamic correlation effects.
  • GNOF and GNOFm present a straightforward approach to electron correlation without complex approximations.
  • These functionals are suitable for studying essential substructures in larger molecules.