Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust (8) supramolecular motif (even when disordered)
Identifieur interne : 000541 ( Main/Exploration ); précédent : 000540; suivant : 000542Hydrogen-bonded molecular salts of reduced benzothiazole derivatives with carboxylates: a robust (8) supramolecular motif (even when disordered)
Auteurs : Mohammed A. E. Shaibah [Inde] ; Belakavadi K. Sagar [Inde] ; Hemmige S. Yathirajan [Inde] ; David B. Cordes ; Alexandra M. Z. Slawin ; William T. A. HarrisonSource :
- Acta Crystallographica Section E: Crystallographic Communications [ 2056-9890 ] ; 2019.
Abstract
The syntheses and structures of five molecular salts of protonated 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (C11H19N2S+) with different deprotonated carboxylic acids (4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric acid and succinic acid) are reported·In every case, the cation protonation occurs at the N atom of the thiazole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methylene groups are disordered over two sets of sites). The C—N bond lengths of the nominal –NH+=C—NH2 fragment of the cation are indistinguishable, indicating a significant contribution of the –NH—C=N+H2 resonance form to the structure.
Url:
DOI: 10.1107/S2056989018018224
PubMed: 30800445
PubMed Central: 6362640
Affiliations:
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(8) supramolecular motif (even when disordered)</title>
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<front><div type="abstract" xml:lang="en"><p>The syntheses and structures of five molecular salts of protonated 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
) with different deprotonated carboxylic acids (4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric acid and succinic acid) are reported·In every case, the cation protonation occurs at the N atom of the thiazole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methylene groups are disordered over two sets of sites). The C—N bond lengths of the nominal –NH<sup>+</sup>
=C—NH<sub>2</sub>
fragment of the cation are indistinguishable, indicating a significant contribution of the –NH—C=N<sup>+</sup>
H<sub>2</sub>
resonance form to the structure.</p>
</div>
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