4,5‐Bis(dimethylamino)phenanthrene and 4,5‐Bis(dimethylamino)‐9,10‐dihydrophenanthrene: Syntheses and “Proton Sponge” Properties | Zendy

Saupe Thomas | Zendy; Krieger Claus | Zendy; Staab Heinz A. | Zendy

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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.

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