An electronic properties investigation to interpret the substituent constants of monosubstituted benzene derivatives

Manassir, Mohammad; Pakiari, A.H.

doi:10.1016/j.jmgm.2019.07.017

Cited by 6 publications

(1 citation statement)

References 51 publications

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“…Our results are also in agreement with earlier studies on electronic effect of X substituent, in particular its donating and accepting properties, changing only to a little extend the aromaticity of benzene ring [48][49][50][51]. On the other hand, olefins are significantly more sensitive to such effects, including "push-pull cases") [52].…”

Section: Electronegativity Of X Substituent and Nbo Charge At C5 Atomsupporting

confidence: 92%

On the aromaticity of uracil and its 5-halogeno derivatives as revealed by theoretically derived geometric and magnetic indexes

et al. 2020

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The problem of aromaticity in heterocyclic rings of uracil and its 5-halogenoderivatives (5XU) was analyzed theoretically by calculating modified harmonic oscillator model of aromaticity (HOMA) for Heterocycle Electron Delocalization (HOMHED), nucleus-independent chemical shift parameters (NICS) and the so-called scan experiments, using helium-3 atom as a magnetic probe. The impact of halogen electronegativity on C5 atom’s NBO charges was also investigated. Water, as a polar environment, has a negligible impact on 5XU aromaticity. The most stable diketo tautomer shows a very low aromaticity while the “rare” dihydroxy form (tautomer No 6) is aromatic and resembles benzene. This is in agreement with traditional drawing of chemical formula of uracil’s six-membered ring, directly showing three alternating single and double bonds in its tautomer No 6. No good correlation between magnetic and geometric indexes of aromaticity for the studied 5XU tautomers was found. Linear correlation between the magnitude of NICS minimum, as well as the distance of the minimum above uracil ring plane center from 3He NMR chemical shift scan plot with respect to halogen electronegativity were observed. A strong linear dependence of magnetic index of aromaticity and the electronegativity of 5X substituent was observed.

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Section: Electronegativity Of X Substituent and Nbo Charge At C5 Atomsupporting

confidence: 92%

On the aromaticity of uracil and its 5-halogeno derivatives as revealed by theoretically derived geometric and magnetic indexes

et al. 2020

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Understanding the impact of surfactants on semiconductor CdSe nanoclusters: a computational study

Singh,

Thareja,

Kakkar

2024

J Nanopart Res

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The structure-activity relationship of aromatic compounds in advanced oxidation processes：a review

Ren

Sun

et al. 2022

Chemosphere

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An electronic properties investigation to interpret the substituent constants of monosubstituted benzene derivatives

Cited by 6 publications

References 51 publications

On the aromaticity of uracil and its 5-halogeno derivatives as revealed by theoretically derived geometric and magnetic indexes

On the aromaticity of uracil and its 5-halogeno derivatives as revealed by theoretically derived geometric and magnetic indexes

Understanding the impact of surfactants on semiconductor CdSe nanoclusters: a computational study

The structure-activity relationship of aromatic compounds in advanced oxidation processes：a review

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