Issue 12, 2014

Salts of the scissor-shaped racemic host 1,1′-binaphthyl-2,2′-dicarboxylic acid with amines: structure and thermal stability

Abstract

The salts formed between racemic 1,1′-binaphthyl-2,2′-dicarboxylic acid (BNDA) and the amines diethylamine (DEA), di-n-butylamine (DBA), cyclohexylamine (CHA) and dicyclohexylamine (DCHA) are reported. Structure 1, (BNDA2−)(2DEA+), and 2a, (BNDA2−)(2DBA+), resulted from slow evaporation of a solution of BNDA in the respective amine. A competition experiment whereby BNDA was dissolved in a mixture of 60% DEA and 40% DBA resulted in a polymorph of 2a, namely 2b. Slow evaporation of dilute solutions of BNDA with CHA and DCHA resulted in a mixed salt solvate 3, (BNDA2−)(3CHA+)(C7NO2H11)·CHA·H2O, and a salt solvate, 4, (BNDA2−)(2DCHA+)·CH3OH·H2O, respectively. For all the experiments methanol was used as a co-solvent due to BNDA insolubility with the amines. In structure 3 one of the CHA guests reacted with carbon dioxide in the atmosphere to form a carbamate anion, C7NO2H11. The kinetics of desolvation for salts 1, 2a and 2b were also determined.

Graphical abstract: Salts of the scissor-shaped racemic host 1,1′-binaphthyl-2,2′-dicarboxylic acid with amines: structure and thermal stability

Supplementary files

Article information

Article type
Paper
Submitted
31 Oct 2013
Accepted
04 Jan 2014
First published
11 Feb 2014

CrystEngComm, 2014,16, 2462-2469

Salts of the scissor-shaped racemic host 1,1′-binaphthyl-2,2′-dicarboxylic acid with amines: structure and thermal stability

A. Jacobs, N. B. Báthori, R. Y. Kabwit and E. Weber, CrystEngComm, 2014, 16, 2462 DOI: 10.1039/C3CE42215A

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