Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical P.pdf
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Synthesis and Spectroscopic Characterisation of N-Alkyl Quaternary Ammonium Salts Typical P
Molecules 2002, 7, 320-330
molecules
ISSN 1420-3049
Synthesis and Spectroscopic Characterisation of N-Alkyl
Quaternary Ammonium Salts Typical Precursors of Cyanines
A. C. Pardal1, S. S. Ramos2, P. F. Santos1, L. V. Reis1 and P. Almeida2,*
1 Departamento de Química, Universidade de Trás-os-Montes e Alto Douro, Apartado 202, 5001-911
Vila Real Codex, Portugal. Tel. 351(259)350273, Fax 351(259)350480
2 Departamento de Química e Unidade de Materiais Têxteis e Papeleiros, Universidade da Beira
Interior, Rua Marquês dávila e Bolama, 6200-001 Covilh?, Portugal. Tel. 351(275)319761, Fax
351(275)319730
* Author to whom correspondence should be addressed; e-mail: pjsa@alpha2.ubi.pt
Received: 23 October 2001; in revised form 18February 2002 / Accepted: 26 February 2002 /
Published: 31 March 2002
Abstract: The synthesis and spectroscopic characterisation of some representative N-alkyl-
substituted quaternary ammonium salts derived from benzothiazole, benzoxazole, benzo-
selenazole, indole and quinoline are described. These heterocyclic salts, bearing an activated
methyl group in the 2-position in relation to the nitrogen atom and N-methyl, -pentyl, -hexyl
and -decyl chains, are typical precursors of cyanine dyes.
Keywords: Heterocyclic quaternary ammonium salts, cyanines precursors, spectroscopic
characterisation.
Introduction
Despite the fact that several N-alkyl quaternary ammonium salts bearing a 2-methylbenzothiazole,
-benzoselenazole, -benzoxazole, -indole and -quinoline nuclei are easily found in the literature, mainly
as unisolated precursors of cyanine dyes [1-3], their full physical and spectroscopic characterisation is
Molecules 2002, 7
321
not usually described. To the best of our knowledge, for some of those most commonly used for the
synthesis of cyanines, namely the N-ethyl, -pentyl, -hexyl and -decyl substituted ones, only the
1H-NMR spectral data for the N-ethyl quaternary salts [4,5] and the 13C-NMR spectral data for
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