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Novel, Very Strongly Basic, Pentacyclic “Proton Sponges” with Vinamidine Structure
Author(s) -
Schwesinger Reinhard,
Mißfeldt Michael,
Peters Karl,
von Schnering Hans Georg
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198711651
Subject(s) - intramolecular force , proton , hydrogen bond , nucleophile , sponge , chemistry , stereochemistry , computational chemistry , molecule , physics , organic chemistry , catalysis , biology , quantum mechanics , botany
The pentacyclic compounds 1–3 are thermodynamically very strong and kinetically active “proton sponges,” which are obtainable by means of symmetric construction from 4 . In addition, they exhibit a relatively high nucleophilicity. Despite a short distance (254.1 pm) between the two N atoms involved, the intramolecular hydrogen bond in 3‐H ⊕ is unsymmetrical.