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  Structural Elucidation of Enantiopure and Racemic 2-Bromo-3-Methylbutyric Acid

Seidel, R. W., Nöthling, N., Goddard, R., & Lehmann, C. W. (2020). Structural Elucidation of Enantiopure and Racemic 2-Bromo-3-Methylbutyric Acid. Chemistry, 2(3), 691-699. doi:10.3390/chemistry2030044.

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 Urheber:
Seidel, Rüdiger W.1, Autor
Nöthling, Nils2, Autor           
Goddard, Richard2, Autor           
Lehmann, Christian W.2, Autor           
Affiliations:
1Martin-Luther-Universität Halle-Wittenberg, Institut für Pharmazie, Wolfgang-Langenbeck-Str. 4, 06120 Halle (Saale), Germany, ou_persistent22              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Schlagwörter: 2-bromo-3-methylbutyric acid; 2-bromo-3-methylbutanoic acid; 2-bromoisovaleric acid; halogenated carboxylic acid; hydrogen bonding; chirality; absolute configuration; racemate; crystal structure; X-ray crystallography
 Zusammenfassung: Halogenated carboxylic acids have been important compounds in chemical synthesis
and indispensable research tools in biochemical studies for decades. Nevertheless, the number of
structurally characterized simple α-brominated monocarboxylic acids is still limited. We herein
report the crystallization and structural elucidation of (R)- and rac-2-bromo-3-methylbutyric acid
(2-bromo-3-methylbutanoic acid, 1) to shed light on intermolecular interactions, in particular hydrogen
bonding motifs, packing modes and preferred conformations in the solid-state. The crystal structures of
(R)- and rac-1 are revealed by X-ray crystallography. Both compounds crystallize in the triclinic crystal
system with Z = 2; (R)-1 exhibits two crystallographically distinct molecules. In the crystal, (R)-1 forms
homochiral O–H···O hydrogen-bonded carboxylic acid dimers with approximate non-crystallographic
C2 symmetry. In contrast, rac-1 features centrosymmetric heterochiral dimers with the same carboxy
syn···syn homosynthon. The crystal packing of centrosymmetric rac-1 is denser than that of its
enantiopure counterpart (R)-1. The molecules in both crystal structures adopt a virtually identical
staggered conformation, despite different crystal environments, which indicates a preferred molecular
structure of 1. Intermolecular interactions apart from classical O–H···O hydrogen bonds do not appear
to have a crucial bearing on the solid-state structures of (R)- and rac-1.

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Sprache(n): eng - English
 Datum: 2020-06-172020-05-272020-07-172020-07-30
 Publikationsstatus: Online veröffentlicht
 Seiten: 9
 Ort, Verlag, Ausgabe: -
 Inhaltsverzeichnis: -
 Art der Begutachtung: Expertenbegutachtung
 Identifikatoren: DOI: 10.3390/chemistry2030044
 Art des Abschluß: -

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Titel: Chemistry
  Kurztitel : Chemistry
Genre der Quelle: Zeitschrift
 Urheber:
Affiliations:
Ort, Verlag, Ausgabe: Basel, Switzerland : MDPI
Seiten: - Band / Heft: 2 (3) Artikelnummer: - Start- / Endseite: 691 - 699 Identifikator: ISSN: 2624-8549
CoNE: https://pure.mpg.de/cone/journals/resource/111076342752076