Revisiting aromaticity of five-membered rings: a dissected ring current analysis

IF 2.9 3区化学 Q3 CHEMISTRY, PHYSICAL

Chemical Physics Letters Pub Date : 2026-03-16 Epub Date: 2026-01-24 DOI:10.1016/j.cplett.2026.142680

Rodrigo Báez-Grez , Ricardo Pino-Rios

引用次数: 0

Abstract

The aromaticity of five-membered heteroaromatic rings (C₄H₄X, X = CH⁻, NH, O, S, Se, Te) was evaluated using dissected ring current strength (RCS) calculations via the GIAO-CD method. Although total RCS values suggest thiophene is more aromatic than pyrrole, π-electron contributions (RCS_π) establish the order: CH⁻ > NH > S > Se > O > Te. This trend is explained as heteroatom's ability to donate its lone-pair, electronegativity, and conjugation efficiency. Comparison with NICS(1)_zz,π aligns with RCS_π, whereas total NICS is distorted by the other contributions, highlighting RCS_π as a more reliable aromaticity descriptor, particularly for heterocycles containing heavier elements.

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重新审视五元环的芳香性：解剖环电流分析

采用GIAO-CD法计算解剖环电流强度（RCS），评价了五元杂芳环（C₄H₄X, X = CH−,nh0， S, Se, Te）的芳构性。虽然总RCS值表明噻吩比吡咯更芳香，但π电子贡献值（RCSπ）确定的顺序为：CH−>； NH > S > Se > O > Te。这一趋势被解释为杂原子提供其孤对、电负性和共轭效率的能力。与NICS(1)zz相比，π与RCSπ一致，而总NICS被其他贡献扭曲，突出RCSπ是更可靠的芳性描述符，特别是对于含有重元素的杂环。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemical Physics Letters 化学-物理：原子、分子和化学物理

CiteScore

5.70

自引率

3.60%

发文量

798

审稿时长

33 days

期刊介绍： Chemical Physics Letters has an open access mirror journal, Chemical Physics Letters: X, sharing the same aims and scope, editorial team, submission system and rigorous peer review. Chemical Physics Letters publishes brief reports on molecules, interfaces, condensed phases, nanomaterials and nanostructures, polymers, biomolecular systems, and energy conversion and storage. Criteria for publication are quality, urgency and impact. Further, experimental results reported in the journal have direct relevance for theory, and theoretical developments or non-routine computations relate directly to experiment. Manuscripts must satisfy these criteria and should not be minor extensions of previous work.