Crystal structures and hydrogen bonding in the anhydrous tryptaminium salts of the isomeric (2,4-dichlorophenoxy)acetic and (3,5-dichlorophenoxy)acetic acids


Autoria(s): Smith, Graham; Lynch, Daniel E.
Data(s)

01/06/2015

Resumo

The anhydrous salts of 1<i>H</i>-indole-3-ethanamine (tryptamine) with isomeric (2,4-dichlorophenoxy)acetic acid (2,4-D) and (3,5-dichlorophenoxy)acetic (3,5-D), C10H13N2+ (C8H5Cl2O3)-, [(I) and (II), respectively] have been determined and their one-dimensional hydrogen-bonded polymeric structures are described. In the crystal of (I),the aminium H-atoms are involved in three separate inter-species N-H...O hydrogen-bonding interactions, two with carboxyl O-atom acceptors and the third in an asymmetric three-centre bidentate carboxyl O,O' chelate [graph set R2/1(4)]. The indole H-atom forms an N-H...O~carboxyl~ hydrogen bond, extending the chain structure along the b axial direction. In (II), two of the three aminium H-atoms are also involved in N-H...O(carboxyl) hydrogen bonds similar to (I) but with the third, a three-centre asymmetric interaction with carboxyl and phenoxy O-atoms is found [graph set R2/1(5)]. The chain polymeric extension is also along b. There are no pi--pi ring interactions in either of the structures. The aminium side chain conformations differ significantly between the two structures, reflecting the conformational ambivalence of the tryptaminium cation, as found also in the benzoate salts.

Formato

application/pdf

Identificador

http://eprints.qut.edu.au/84593/

Publicador

International Union of Crystallography (IUCr)

Relação

http://eprints.qut.edu.au/84593/1/TRYPPHEN.pdf

DOI:10.1107/S205698901500907X

Smith, Graham & Lynch, Daniel E. (2015) Crystal structures and hydrogen bonding in the anhydrous tryptaminium salts of the isomeric (2,4-dichlorophenoxy)acetic and (3,5-dichlorophenoxy)acetic acids. Acta Crystallographica Section E: Crystallographic Communications, 71(6), pp. 671-674.

Direitos

Copyright 2015 International Union of Crystallography

This open-access article is distributed under the terms of the Creative Commons Attribution Licence http://creativecommons.org/licenses/by/2.0/uk/legalcode, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Fonte

School of Chemistry, Physics & Mechanical Engineering; Science & Engineering Faculty

Palavras-Chave #crystal structures #tryptamine #phenoxyacetic acids #herbicides #hydrogen bonding
Tipo

Journal Article