Surprising acidity for the methylene of 1,3-indenocorannulenes?

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2024-12-02 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.260

Shi Liu, Märt Lõkov, Sofja Tshepelevitsh, Ivo Leito, Kim K Baldridge, Jay S Siegel

引用次数: 0

Abstract

Quantitative assessment of the first acidity constant (pK _a) for BFC (27.6 in CH₃CN) and FIC (27.8 in CH₃CN) shows the methylene protons to be significantly more acidic than those in related cyclopentadiene (32 in CH₃CN), indene (34 in CH₃CN), or fluorene (37 in CH₃CN) and comparable to the methine of 9-perfluorophenylfluorene (28.14 in CH₃CN). This work reports quantitative pK _a values of BFC and FIC, places those values in a broadened context of CpH-cognate hydrocarbon acidity and presents a Clar-Loschmidt graph perspective to help understand the "surprises".

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令人惊讶的1,3-吲哚环烯亚甲基的酸度？

定量评价BFC （CH3CN中为27.6）和FIC （CH3CN中为27.8）的第一酸度常数（pK a）表明，亚甲基质子的酸性明显高于相关的环pentadiene （CH3CN中为32）、茚（CH3CN中为34）和芴（CH3CN中为37），与9-全氟苯基芴的甲基（CH3CN中为28.14）相当。这项工作报告了BFC和FIC的定量pK值，将这些值置于cph同源烃酸度的更广泛背景下，并提出了一个Clar-Loschmidt图视角，以帮助理解“惊喜”。

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

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.