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

被引：0
|
作者：
Liu, Shi [1 ]
Lokov, Maert [2 ]
Tshepelevitsh, Sofja [2 ]
Leito, Ivo [2 ]
Baldridge, Kim K. [1 ]
Siegel, Jay S. [1 ]
机构：
[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin, Peoples R China
[2] Univ Tartu, Inst Chem, Ravila 14a, EE-50411 Tartu, Estonia
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 20卷
关键词：
acidity; aromatic hydrocarbon; Clar sextet; Loschmidt group element; molecular graph; EQUILIBRIUM ACIDITIES; DESIGN; CARBON; PRINCIPLES; STABILITY; CRYSTAL; BENZENE; SCALE;
D O I：
10.3762/bjoc.20.260
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Quantitative assessment of the first acidity constant (pKa) 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 pKa 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".
引用
收藏
页码：3144 / 3150
页数：7
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