Issue 8, 2001
From the journal:

Journal of the Chemical Society, Dalton Transactions

Aluminium and gallium compounds of salicylic and anthranilic acids: examples of weak intra-molecular hydrogen bonding

Catherine S. Branch,a   Janusz Lewinski,*b   Iwona Justyniak,b   Simon G. Bott,c   Janusz Lipkowskid  and  Andrew R. Barron*a  

* Corresponding authors

a Department of Chemistry, Rice University, Houston, Texas, USA
E-mail: arb@rice.edu

b Department of Chemistry, Warsaw University of Technology, Noakowskiego 3, Warsaw, Poland
E-mail: lewin@ch.pw.edu.pl

c Department of Chemistry, University of Houston, Houston, Texas, USA

d Institute of Physical Chemistry, Polish Academy of Sciences, Kasparzaka 44/52, Warsaw, Poland

Abstract

Reaction of M(tBu)3 with anthranilic, salicylic and ortho-toluic acids yields [(tBu)2M(μ-O2CC6H4-2-NH2)]2, M = Al (1), Ga (2), [(tBu)2Ga(μ-O2CC6H4-2-OH)]2 (3), and [(tBu)2Ga(μ-O2CC6H4-2-Me)]2 (4), respectively. Reaction of anthranilic acid with two equivalents of Al(tBu)3 allows for the isolation of (tBu)2Al(μ-O2CC6H4-2-NH2)Al(tBu)3 (5). Compounds 1–5 have been characterized by NMR and IR spectroscopy, mass spectrometry, and X-ray crystallography. The presence of intra-molecular hydrogen bonding, in compounds 1–3, is probed by the orientation of the aromatic rings. Compound 5 is proposed to be a Lewis acid stabilized complex of the intermediate in the synthesis of compound 1.

Graphical abstract: Aluminium and gallium compounds of salicylic and anthranilic acids: examples of weak intra-molecular hydrogen bonding

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Article information

DOI
https://doi.org/10.1039/B008858G
Article type
Paper
Submitted
01 Nov 2000
Accepted
08 Feb 2001
First published
30 Mar 2001

J. Chem. Soc., Dalton Trans., 2001, 1253-1258

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Aluminium and gallium compounds of salicylic and anthranilic acids: examples of weak intra-molecular hydrogen bonding

C. S. Branch, J. Lewinski, I. Justyniak, S. G. Bott, J. Lipkowski and A. R. Barron, J. Chem. Soc., Dalton Trans., 2001, 1253 DOI: 10.1039/B008858G

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