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
相关论文
共 50 条
  • [41] REACTIONS OF ACTIVE METHYLENE COMPOUNDS WITH 1,3-DIENES CATALYZED BY NICKEL COMPLEXES
    BAKER, R
    COOK, AH
    SMITH, TN
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (12): : 1517 - 1524
  • [42] THERMAL-BEHAVIOR AND CHARACTERIZATION OF POLY[1,3-PHENYLENEBIS (METHYLENE)ADIPAMIDE]
    SHIMASAKI, C
    SANAGI, H
    UNISHI, A
    NOTOYA, H
    TSUKURIMICHI, E
    YOSHIMURA, T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (03) : 983 - 989
  • [43] Enantioselective 1,3-Dipolar Cycloadditions of a-Methylene Lactams to Construct Spirocycles
    Nishiura, Yuji
    Gonzalez, Kevin J.
    Cusumano, Alexander Q.
    Stoltz, Brian M.
    ORGANIC LETTERS, 2023, 25 (35) : 6469 - 6473
  • [44] Bis(hydroxymethylation) of the active methylene group of 1,3-dicarbonyl and related compounds
    Guzaev, A
    Lonnberg, H
    SYNTHESIS-STUTTGART, 1997, (11): : 1281 - 1284
  • [45] N,N'-[1,3-Phenylenebis(methylene)]di-p-toluenesulfonamide
    Ejaz
    Khan, Islam Ullah
    Harrison, William T. A.
    Anjum, Rukhsana
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O950 - +
  • [46] 1,3-DIPOLAR CYCLOADDITIONS .45. ADDITION OF NITRONES TO METHYLENE PHOSPHORANES
    HUISGEN, R
    WULFF, J
    CHEMISCHE BERICHTE-RECUEIL, 1969, 102 (03): : 746 - &
  • [47] Synthesis, characterization and computational studies of 1,3-bis[(E)-furan-2-yl)methylene]urea and 1,3-bis[(E)-furan-2-yl)methylene]thiourea
    Alabi, Kazeem Adelani
    Abdulsalami, Ibrahim Olasegun
    Adeoye, Moriam Dasola
    Aderinto, Shukurat Modupe
    Adigun, Rasheed Adewale
    PHYSICAL SCIENCES REVIEWS, 2022, 7 (08) : 923 - 931
  • [48] 6,6'-Dimethyl-2,2'-[1,3-diazinane-1,3-diylbis(methylene)] diphenol
    Rivera, Augusto
    Marcela Gonzalez, Derly
    Rios-Motta, Jaime
    Fejfarova, Karla
    Dusek, Michal
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O698 - U2031
  • [49] 2-METHYLTHIOMETHYLATION OF 1,3-DICARBONYL COMPOUNDS AND SYNTHESIS OF 2-METHYLENE-1,3-DICARBONYL COMPOUNDS
    YAMAUCHI, M
    KATAYAMA, S
    WATANABE, T
    SYNTHESIS-STUTTGART, 1982, (11): : 935 - 937
  • [50] ASYMMETRIC-SYNTHESIS AND CYCLOADDITION CHEMISTRY OF TRANS-2-METHYLENE-1,3-DITHIOLANE 1,3-DIOXIDE
    AGGARWAL, VK
    GRAINGER, RS
    SPARGO, PL
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 95-6 (1-4): : 337 - 338
12345