English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  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.

Item is

Basic

show hide
Genre: Journal Article

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Seidel, Rüdiger W.1, Author
Nöthling, Nils2, Author              
Goddard, Richard2, Author              
Lehmann, Christian W.2, Author              
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              

Content

show
hide
Free keywords: 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
 Abstract: 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.

Details

show
hide
Language(s): eng - English
 Dates: 2020-06-172020-05-272020-07-172020-07-30
 Publication Status: Published online
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.3390/chemistry2030044
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Chemistry
  Abbreviation : Chemistry
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Basel, Switzerland : MDPI
Pages: - Volume / Issue: 2 (3) Sequence Number: - Start / End Page: 691 - 699 Identifier: ISSN: 2624-8549
CoNE: https://pure.mpg.de/cone/journals/resource/111076342752076