Crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues

Smith, Graham & Lynch, Daniel E. (2015) Crystal structures and hydrogen bonding in the morpholinium salts of four phenoxyacetic acid analogues. Acta Crystallographica Section E: Crystallographic Communications, E71, pp. 1392-1396.

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The anhydrous salts morpholinium (tetrahydro-2-H-1,4-oxazine) phenxyacetate, C4H10NO+ C8H7O3- (I), (4-fluorophenoxy)acetate, C4H10NO+ C8H6FO3- (II) and isomeric morpholinium (3,5-dichlorophenoxy)acetate (3,5-D) (III) and morpholinium (2,4-dichlorophenoxy)acetate (2,4-D), C4H10NO+ C8H5Cl2O3- (IV), have been determined and their hydrogen-bonded structures are described. In the crystals of (I), (III) and (IV), one of the the aminium H atoms is involved in a three-centre asymmetric cation-anion N-H...O,O' R2/1(4) hydrogen-bonding interaction with the two carboxyl O-atom acceptors of the anion. With the structure of (II), the primary N---H...O interaction is linear. In the structures of (I), (II) and (III), the second N-H...O(carboxyl) hydrogen bond generates one-dimensional chain structures extending in all cases along [100]. With (IV), the ion pairs are linked though inversion-related N-H...O hydrogen bonds [graph set R2/4(8)], giving a cyclic heterotetrameric structure.

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ID Code: 89669
Item Type: Journal Article
Refereed: Yes
Additional URLs:
Keywords: morpholinium salt, phenoxyacetic acids, hydrogen bonding, crystal structure, herbicides
DOI: 10.1107/S2056989015019842
ISSN: 2056-9890
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Copyright Owner: Copyright 2015 International Union of Crystallography
Copyright Statement: This open-access article is distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Deposited On: 30 Oct 2015 00:01
Last Modified: 05 Nov 2015 23:44

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