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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Yathirajan</name><affiliation wicri:level="1"><nlm:aff id="a">Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006,<country>India</country></nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Cordes, David B" sort="Cordes, David B" uniqKey="Cordes D" first="David B." last="Cordes">David B. Cordes</name><affiliation><nlm:aff id="b">School of Chemistry, University of St Andrews, Fife KY16 9ST,<country>Scotland</country></nlm:aff><wicri:noCountry code="nlm country">Scotland</wicri:noCountry></affiliation></author><author><name sortKey="Slawin, Alexandra M Z" sort="Slawin, Alexandra M Z" uniqKey="Slawin A" first="Alexandra M. Z." last="Slawin">Alexandra M. Z. Slawin</name><affiliation><nlm:aff id="b">School of Chemistry, University of St Andrews, Fife KY16 9ST,<country>Scotland</country></nlm:aff><wicri:noCountry code="nlm country">Scotland</wicri:noCountry></affiliation></author><author><name sortKey="Harrison, William T A" sort="Harrison, William T A" uniqKey="Harrison W" first="William T. A." last="Harrison">William T. A. Harrison</name><affiliation><nlm:aff id="c">Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE,<country>Scotland</country></nlm:aff><wicri:noCountry code="nlm country">Scotland</wicri:noCountry></affiliation></author></analytic><series><title level="j">Acta Crystallographica Section E: Crystallographic Communications</title><idno type="eISSN">2056-9890</idno><imprint><date when="2019">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><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></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>Inde</li></country></list><tree><noCountry><name sortKey="Cordes, David B" sort="Cordes, David B" uniqKey="Cordes D" first="David B." last="Cordes">David B. 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