Work

Comparison of Various Theoretical Measures of Aromaticity within Monosubstituted Benzene

Year: 2024

Type: article

Abstract: The effects of monosubstitution on the aromaticity of benzene are assessed using a number of different quantitative schemes. The ability of the mobile π-electrons to respond to an external magnetic field is evaluated using several variants of the NICS scheme which calculate the shielding of points along the axis perpendicular to the molecule. Another class of measures is related to the drive toward the uniformity of C-C bond lengths and strengths. Several energetic quantities are devised to approximate an aromatic stabilization energy and the tendency of the molecule to maintain planarity. There is a lack of consistency in that the various measures of aromaticity lead to differing conclusions as to the effects of substituents on the aromaticity of the ring.

Source: Molecules

DOI: 10.3390/molecules29102260

Authors: Caleb K. Swain, Steve Scheiner

Institution: Utah State University

Language: English

Topic: Synthesis and Properties of Aromatic Compounds

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,069

Funder: National Science Foundation