Polarized Naphthalimide CH Donors Enhance Cl– Binding within an Aryl-Triazole Receptor

The dipolar character of 1,8-naphthalimide together with polarization of the C4–H and C5–H donors has been utilized in receptor 1 to effectively bind chloride alongside triazole and phenylene units. The Cl– binding strength of 1 shows that the naphthalimide provides greater anion stabilization than...

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Veröffentlicht in:Organic letters 2011-12, Vol.13 (23), p.6260-6263
Hauptverfasser: McDonald, Kevin P, Ramabhadran, Raghunath O, Lee, Semin, Raghavachari, Krishnan, Flood, Amar H
Format: Artikel
Sprache:eng
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Zusammenfassung:The dipolar character of 1,8-naphthalimide together with polarization of the C4–H and C5–H donors has been utilized in receptor 1 to effectively bind chloride alongside triazole and phenylene units. The Cl– binding strength of 1 shows that the naphthalimide provides greater anion stabilization than an unactivated phenylene, and DFT calculations show that its collinear donor array can be a “urea-like” analog for CH···anion interactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202729z