Crystal structures and hydrogen bonding in the proton transfer salts of nicotine with 3,5-dinitrosalicylic acid and 5-sulfosalicylic acid


Autoria(s): Smith, Graham; Wermuth, Urs D.
Data(s)

01/11/2014

Resumo

The structures of the 1:1 anhydrous salts of nicotine (NIC) with 3,5-dinitrosalicylic acid (DNSA) and 5-sulfosalicylic acid (5-SSA), namely (1R,2S)-1-methyl-2-(3-pyridyl)-1H-pyrrolidin-1-ium 2-carboxy-4,6-dinitrophenolate, C10H15N2+ C7H3N2O7-, (I) and (1R,2S)-1-methyl-2-(3-pyridyl)-1H-pyrrolidin-1-ium 3-carboxy-4-hydroxybenzenesulfonate, C10H15N2+ C7H5O6S-, (II) are reported. The asymmetric units of both (I) and (II) comprise two independent nicotinium cations (C and D) and either two DNSA or two 5-SSA anions (A and B), respectively. One of the DNSA anions shows a 25% rotational disorder in the benzene ring system. In the crystal of (I), inter-unit pyrrolidinium N-H...N(pyridine) hydrogen bonds generate zigzag NIC cation chains which extend along a while the DNSA anions are not involved in any formal inter-species hydrogen bonding but instead form pi--pi associated stacks which parallel the NIC chains along a [ring centroid separation, 3.857(2)A]. Weak C-H...O interactions between chain substructures give an overall three-dimensional structure. With (II), A and B anions form independent zigzag chains with C and D cations, respectively, through carboxylic acid O-H...N(pyridine) hydrogen bonds. These chains, which extend along b are pseudo-centrosymmetrically related and give pi--pi interactions between the benzene rings of anions A and B and the pyridine rings of the NIC cations C and D, respectively [ring centroid separations, 3.6422(19) and 3.7117(19)A]. Present also are weak intermolecular C-H...O hydrogen-bonding interactions between the chains, giving an overall three-dimensional structure.

Formato

application/pdf

Identificador

http://eprints.qut.edu.au/83148/

Publicador

Wiley-Blackwell Publishing, Inc.

Relação

http://eprints.qut.edu.au/83148/1/NIC.PDF

http://scripts.iucr.org/cgi-bin/paper?S1600536814023253

DOI:10.1107/S1600536814023253

Smith, Graham & Wermuth, Urs D. (2014) Crystal structures and hydrogen bonding in the proton transfer salts of nicotine with 3,5-dinitrosalicylic acid and 5-sulfosalicylic acid. Acta Crystallographica. Section E: Structure Reports Online, 70, pp. 430-434.

Direitos

Copyright 2014 International Union of Crystallography

Fonte

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

Palavras-Chave #crystal structure #proton-transfer compounds #nicotine #3,5-dinitrosalicylic acid #5-sulfosalicylic acid
Tipo

Journal Article