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Tetracyanohydroquinone and its Dimorpholinium Salt: Hydrogen Bonds OH … N or O ⊖ H ⊕ N to Nitrogen Bases of Different Strengths
Author(s) -
Bock Hans,
Seitz Wolfgang,
Havlas Zdenek,
Bats Jan W.
Publication year - 1993
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.199304111
Subject(s) - hydrogen bond , chemistry , hydrogen , molecule , salt (chemistry) , morpholine , proton , nitrogen , acceptor , crystallography , stereochemistry , medicinal chemistry , organic chemistry , physics , quantum mechanics , condensed matter physics
How a network of hydrogen bonds is influenced by the basicity of a proton acceptor center is demonstrated particularly clearly by the title compounds: tetracyanohydroquinone, a relatively acidic phenol, forms linear molecular strings by self‐association through hydrogen bonds between OH and CN groups—provided that addition of a stronger base such as morpholine does not cause hydrogen bonds to be formed preferentially between different molecules, with concomitant hydrogen transfer (see below).