Exploring Cyclopentadienone Antiaromaticity: Charge Density Studies of Various Tetracyclones

A systematic study of six tetracyclones has been carried out using experimental and theoretical charge density analysis. A three pronged approach based on quantum theory of atoms in molecules (QTAIM), nucleus independent chemical shifts (NICS) criterion, and source function (SF) contributions has be...

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Bibliographic Details
Published in:The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2014-05, Vol.118 (19), p.3479-3489
Main Authors: Pal, Rumpa, Mukherjee, Somnath, Chandrasekhar, S, Guru Row, T. N
Format: Article
Language:English
Subjects:
Charge density
Criteria
Derivatives
Nuclei
Physical chemistry
Polarity
Quantum theory
Spectroscopy
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Summary:A systematic study of six tetracyclones has been carried out using experimental and theoretical charge density analysis. A three pronged approach based on quantum theory of atoms in molecules (QTAIM), nucleus independent chemical shifts (NICS) criterion, and source function (SF) contributions has been performed to establish the degree of antiaromaticity of the central five-membered ring in all the derivatives. Electrostatic potentials mapped on the isodensity surface show that electron withdrawing substituents turn both C and O atoms of the carbonyl group more electropositive while retaining the direction of polarity.
ISSN:1089-5639
1520-5215
DOI:10.1021/jp5010924