Novel, Very Strongly Basic, Pentacyclic “Proton Sponges” with Vinamidine Structure | Zendy

Schwesinger Reinhard | Zendy; Mißfeldt Michael | Zendy; Peters Karl | Zendy; von Schnering Hans Georg | Zendy

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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.

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