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Addressing Hydrogen Bonding Motifs by Suited Substitution of Thioureas
Author(s) -
Hollmann Katharina,
Oppermann Alexander,
Amen Maike,
Flörke Ulrich,
Egold Hans,
Hoffmann Alexander,
HerresPawlis Sonja,
Henkel Gerald
Publication year - 2016
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201600126
Subject(s) - hydrogen bond , chemistry , substitution (logic) , resonance (particle physics) , catalysis , computational chemistry , structural motif , characterization (materials science) , molecule , crystallography , chemical physics , materials science , nanotechnology , organic chemistry , computer science , atomic physics , programming language , biochemistry , physics
The possibility to form hydrogen bonds with different motifs is an interesting aspect of the chemistry of thioureas especially regarding catalysis. We present nine new thioureas with different unsymmetric substitution patterns involving aromatic and aliphatic substituents including the structural characterization of four of them. Herein, three different hydrogen bond patterns could be realized. Moreover, DFT calculations were performed to investigate the strength of the hydrogen bonds. Hereby, we show that we can selectively address different hydrogen bonding motifs by the choice of substituents. This enables a correlation of the molecular structure and the bonding motifs. Additionally, by natural resonance theory, we show that the contribution of the thiolate resonance form dominates the electronic structure, which is important for coordination chemistry.