Surprising acidity for the methylene of 1,3-indenocorannulenes?
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 o...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2024-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.20.260 |
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| author | Shi Liu Märt Lõkov Sofja Tshepelevitsh Ivo Leito Kim K. Baldridge Jay S. Siegel |
| author_facet | Shi Liu Märt Lõkov Sofja Tshepelevitsh Ivo Leito Kim K. Baldridge Jay S. Siegel |
| author_sort | Shi Liu |
| collection | DOAJ |
| description | 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”. |
| format | Article |
| id | doaj-art-c613fc6459f34871a004f2342bc4fabd |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-c613fc6459f34871a004f2342bc4fabd2025-01-06T12:27:36ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972024-12-012013144315010.3762/bjoc.20.2601860-5397-20-260Surprising acidity for the methylene of 1,3-indenocorannulenes?Shi Liu0Märt Lõkov1Sofja Tshepelevitsh2Ivo Leito3Kim K. Baldridge4Jay S. Siegel5School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, PR China University of Tartu, Institute of Chemistry, Ravila 14a, Tartu 50411, Estonia University of Tartu, Institute of Chemistry, Ravila 14a, Tartu 50411, Estonia University of Tartu, Institute of Chemistry, Ravila 14a, Tartu 50411, Estonia School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, PR China School of Pharmaceutical Science and Technology, Tianjin University, Tianjin, PR China 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”.https://doi.org/10.3762/bjoc.20.260acidityaromatic hydrocarbonclar sextetloschmidt group elementmolecular graph |
| spellingShingle | Shi Liu Märt Lõkov Sofja Tshepelevitsh Ivo Leito Kim K. Baldridge Jay S. Siegel Surprising acidity for the methylene of 1,3-indenocorannulenes? Beilstein Journal of Organic Chemistry acidity aromatic hydrocarbon clar sextet loschmidt group element molecular graph |
| title | Surprising acidity for the methylene of 1,3-indenocorannulenes? |
| title_full | Surprising acidity for the methylene of 1,3-indenocorannulenes? |
| title_fullStr | Surprising acidity for the methylene of 1,3-indenocorannulenes? |
| title_full_unstemmed | Surprising acidity for the methylene of 1,3-indenocorannulenes? |
| title_short | Surprising acidity for the methylene of 1,3-indenocorannulenes? |
| title_sort | surprising acidity for the methylene of 1 3 indenocorannulenes |
| topic | acidity aromatic hydrocarbon clar sextet loschmidt group element molecular graph |
| url | https://doi.org/10.3762/bjoc.20.260 |
| work_keys_str_mv | AT shiliu surprisingacidityforthemethyleneof13indenocorannulenes AT martlokov surprisingacidityforthemethyleneof13indenocorannulenes AT sofjatshepelevitsh surprisingacidityforthemethyleneof13indenocorannulenes AT ivoleito surprisingacidityforthemethyleneof13indenocorannulenes AT kimkbaldridge surprisingacidityforthemethyleneof13indenocorannulenes AT jayssiegel surprisingacidityforthemethyleneof13indenocorannulenes |