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4,5‐Bis(dimethylamino)phenanthrene and 4,5‐Bis(dimethylamino)‐9,10‐dihydrophenanthrene: Syntheses and “Proton Sponge” Properties
Author(s) -
Saupe Thomas,
Krieger Claus,
Staab Heinz A.
Publication year - 1986
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.198604511
Subject(s) - fluorene , phenanthrene , hydrogen bond , chemistry , sponge , perchlorate , derivative (finance) , proton , medicinal chemistry , polymer chemistry , stereochemistry , molecule , organic chemistry , ion , physics , polymer , botany , quantum mechanics , financial economics , economics , biology
Strong, almost linear N ċ H ċ N hydrogen bonds are present in 1 ‐perchlorate and its 9,10‐dihydro derivative. The N ċ N distance is even shorter and the H/CH 3 bridge coupling stronger than in the analogue with a fluorene skeleton. Unprotonated 1 could be generated via a dichlorinated seven‐membered dibenzosulfone.