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- Publisher Website: 10.1021/acs.jmedchem.0c02147
- Scopus: eid_2-s2.0-85103437477
- PMID: 33685125
- WOS: WOS:000635440600023
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Article: Synthesis and Acidity of 5-(m-Terphenyl-2′-yl)-1 H-tetrazoles: Evidence for an Enhanced Polar-πEffect Compared to Carboxylic Acids
| Title | Synthesis and Acidity of 5-(m-Terphenyl-2′-yl)-1 H-tetrazoles: Evidence for an Enhanced Polar-πEffect Compared to Carboxylic Acids |
|---|---|
| Authors | |
| Issue Date | 2021 |
| Citation | Journal of Medicinal Chemistry, 2021, v. 64, n. 6, p. 3197-3203 How to Cite? |
| Abstract | The polar-πeffect on tetrazoles, medicinal chemistry isosteres of carboxylate, is tested by a Hammett pKa (microtitration) analysis over a series of 5-(m-terphenyl-2′-yl)-1H-tetrazoles. A comparison with m-terphenyl-2′-yl-carboxylic acids supports the isostere analogy also in response to environmental changes. Computational (B97D/def2TZVPPD) extension of the series plus a scan of solvents (vacuum to water) demonstrates the trend with the dielectric constant. The effect is energetically small but may make statistically significant contributions to the tetrazole pharmacological profile. |
| Persistent Identifier | http://hdl.handle.net/10722/341304 |
| ISSN | 2023 Impact Factor: 6.8 2023 SCImago Journal Rankings: 1.986 |
| ISI Accession Number ID |
| DC Field | Value | Language |
|---|---|---|
| dc.contributor.author | Bookser, Brett C. | - |
| dc.contributor.author | Do, Quyen Quyen | - |
| dc.contributor.author | Sritana-Anant, Yongsak | - |
| dc.contributor.author | Baldridge, Kim K. | - |
| dc.contributor.author | Siegel, Jay S. | - |
| dc.date.accessioned | 2024-03-13T08:41:46Z | - |
| dc.date.available | 2024-03-13T08:41:46Z | - |
| dc.date.issued | 2021 | - |
| dc.identifier.citation | Journal of Medicinal Chemistry, 2021, v. 64, n. 6, p. 3197-3203 | - |
| dc.identifier.issn | 0022-2623 | - |
| dc.identifier.uri | http://hdl.handle.net/10722/341304 | - |
| dc.description.abstract | The polar-πeffect on tetrazoles, medicinal chemistry isosteres of carboxylate, is tested by a Hammett pKa (microtitration) analysis over a series of 5-(m-terphenyl-2′-yl)-1H-tetrazoles. A comparison with m-terphenyl-2′-yl-carboxylic acids supports the isostere analogy also in response to environmental changes. Computational (B97D/def2TZVPPD) extension of the series plus a scan of solvents (vacuum to water) demonstrates the trend with the dielectric constant. The effect is energetically small but may make statistically significant contributions to the tetrazole pharmacological profile. | - |
| dc.language | eng | - |
| dc.relation.ispartof | Journal of Medicinal Chemistry | - |
| dc.title | Synthesis and Acidity of 5-(m-Terphenyl-2′-yl)-1 H-tetrazoles: Evidence for an Enhanced Polar-πEffect Compared to Carboxylic Acids | - |
| dc.type | Article | - |
| dc.description.nature | link_to_subscribed_fulltext | - |
| dc.identifier.doi | 10.1021/acs.jmedchem.0c02147 | - |
| dc.identifier.pmid | 33685125 | - |
| dc.identifier.scopus | eid_2-s2.0-85103437477 | - |
| dc.identifier.volume | 64 | - |
| dc.identifier.issue | 6 | - |
| dc.identifier.spage | 3197 | - |
| dc.identifier.epage | 3203 | - |
| dc.identifier.eissn | 1520-4804 | - |
| dc.identifier.isi | WOS:000635440600023 | - |