Structural and spectroscopic studies of the adducts of quinuclidine and 3,5-dinitrobenzoic acid

• Published in: Journal of molecular structure Vol. 688; no. 1; pp. 59 - 65
• Main Authors: Chantrapromma, S, Usman, A, Fun, H.K, Poh, B.L, Karalai, C
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 21-01-2004
• Subjects: 1H NMR spectroscopy; 3,5-Dinitrobenzoic acid; Crystal structure; FT-IR spectroscopy; Intermolecular hydrogen bond; Quinuclidine; Salt-like adducts; FT-IR spectroscopy; Quinuclidine; Intermolecular hydrogen bond; 1H NMR spectroscopy; Salt-like adducts; 3,5-Dinitrobenzoic acid; Crystal structure
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2003.09.003

Two types of adducts of quinuclidine with 3,5-dinitrobenzoic acid, namely quinuclidinium-3,5-dinitrobenzoate and quinuclidinium-3,5-dinitrobenzoate-3,5-dinitrobenzoic acid have been prepared. Their structures were analyzed using X-ray diffraction, FT-IR and
1H NMR spectroscopic methods. In both adducts, there is an H atom transferred from the acid to the quinuclidine N atom creating an ionic pair consisting of the quinuclidinium cation and the 3,5-dinitrobenzoate anion. The N
+–H bond acts as a hydrogen bond donor, whereas the carboxylate group acts as hydrogen bond acceptors.