Strained Aromatic Molecules

Smith, Paul J.; Liebman, Joel F.; Hopf, Henning; Starý, Ivo; Stará̈, Irena G.; Halton, Brian

doi:10.1002/9783527627134.ch4

Cited by 17 publications

(2 citation statements)

References 345 publications

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“…In an attempt to quantify this synthetic challenge, we herein report theoretical calculations on the determination of the strain energy (SE) of CNBs using the Gaussian 09 program with the B3LYP/6-31G(d) level of theory. , Although theoretical studies on the structure, aromaticity, molecular orbitals, energy gaps, and reactivity of CNBs have already been performed, reports on a systematic study of their SEs still remain elusive . The SE of highly strained molecules has a significant impact on their stability and reactivity, which thus determines their synthetic accesibility . The quantitative analysis of the SE of CNBs accordingly represents a desirable research target in order to prepare synthetic studies.…”

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confidence: 99%

A Theoretical Study on the Strain Energy of Carbon Nanobelts

et al. 2016

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A theoretical study on the strain energy of carbon nanobelts, i.e. the belt-shaped molecules representing the sidewall structures of carbon nanotubes, is reported. The strain energy of carbon nanobelts with chiral indices (n,n), (n,0), and (n,m) was determined without considering hypothetical homodesmotic reactions. The calculated difference between the strain energy of carbon nanobelts and their possible precursors is expected to be of great utility for future synthetic purposes.

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A Theoretical Study on the Strain Energy of Carbon Nanobelts

et al. 2016

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“…However, [ n ]meta- and [ n ]paracyclophanes stand out as particularly intriguing examples for studying variations in aromaticity due to their unique bent monobenzene ring structure. Investigating the literature on [ n ]paracyclophanes ([ n ]pCPs) consistently indicates a correlation between the length of the polymethylene bridge and the chemical behaviors exhibited by these compounds. − The short chain of the smallest [ n ]pCPs ([ n < 6]) leads to their inherent instability and difficulty in synthesis. , …”

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Tubular Magnetic Shielding Scan (TMSS): A New Technique for Molecular Space Exploration. (i) The Case of Aromaticity of Benzene and [n]Paracyclophanes

Al-Yassiri

2023

J. Phys. Chem. A

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Both traditional and novel techniques were employed in this work for magnetic shielding evaluation to shed new light on the magnetic and aromaticity properties of benzene and 12 [n]paracyclophanes with n = 3–14. Density functional theory (DFT) with the B3LYP functional and all-electron Jorge-ATZP and x2c-TZVPPall-s basis sets was utilized for geometry optimization and magnetic shielding calculations, respectively. Additionally, the 6-311+G(d,p) basis set was incorporated for the purpose of comparing the magnetic shielding results. In addition to traditional evaluations such as NICS/NICS zz -Scan, and 2D-3D σiso(r)/σ zz (r) maps, two new techniques were implemented: bendable grids (BGs) and cylindrical grids (CGs) of ghost atoms (Bqs). BGs allow for the recording of magnetic shielding from the bent ring levels of [n]pCPs, while CGs provide tubular magnetic shielding scan (TMSS) maps detailing the magnetic shielding from a cylindrical region above and below the ring frame. Our findings suggest that smaller [n]pCPs with n < 6 exhibit deviations in the magnetic shielding above and below the ring, indicating a broken electron delocalization under the ring. In contrast, larger [n]pCPs tend to behave similarly to benzene in terms of magnetic shielding. Moreover, we found that shorter polymethylene chains of [n]pCPs exhibit significantly higher magnetic shielding interactions with the ring. Both of the above techniques offer new and promising tools for characterizing nonplanar aromatic compounds, thereby contributing to a deeper understanding of their magnetic and electronic properties.

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Energetics of Organomanganese Compounds

Liebman

Slayden

2011

Patai's Chemistry of Functional Groups

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Diverse aspects of the energetics of organomanganese compounds are considered in this chapter. Bond energies, enthalpies of formation and enthalpies of reaction are discussed. Classical combustion calorimetry plays only a small role compared to reaction calorimetry and techniques from contemporary ion energetics. While carbonyl, cyano, cyclopentadienyl, and benzene derivatives dominate the discussion, species with numerous other σ and/or π‐bonded ligands also appear. Quantitation is given whenever possible.

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Strained Aromatic Molecules

Cited by 17 publications

References 345 publications

A Theoretical Study on the Strain Energy of Carbon Nanobelts

A Theoretical Study on the Strain Energy of Carbon Nanobelts

Tubular Magnetic Shielding Scan (TMSS): A New Technique for Molecular Space Exploration. (i) The Case of Aromaticity of Benzene and [n]Paracyclophanes

Energetics of Organomanganese Compounds

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