The Intramolecular Hydrogen Bond and Intrinsic Proton Affinity of Neutral Organic Molecule: N, N', N''-tris(3-aminopropyl)guanidine and Some Related Systems (CROSBI ID 93876)
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Podaci o odgovornosti
Kovačević, Borislav ; Glasovac, Zoran ; Maksić, Zvonimir B.
engleski
The Intramolecular Hydrogen Bond and Intrinsic Proton Affinity of Neutral Organic Molecule: N, N', N''-tris(3-aminopropyl)guanidine and Some Related Systems
Multiple aminopropyl substitutions of the initial N, N', N''-trimethylguanidine leads to high intrinsic proton affinities and basicities culminating in APA = 268.4 kcal/mol in N, N', N''-tris(3-aminopropyl)guanidine. The reason behind a high proton affinity is identified as a strong cationic resonance in the central guanidine moiety and the strength of the intramolecular bonding, which is enhanced upon protonation.
basicity; proton affinity; proton sponges; superbases
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