Hydrogen bonding in proton-transfer compounds of 5-sulfosalicylic acid with bicyclic heteroaromatic Lewis bases

Abstract

The crystal structures of quinolinium 3‐carboxy‐4‐hydroxy­benzene­sulfonate trihydrate, C9H8N+·C7H5O6S−·3H2O, (I), 8‐hydroxy­quinolinium 3‐carboxy‐4‐hydroxy­benzene­sulfonate monohydrate, C9H8NO+·C7H5O6S−·H2O, (II), 8‐amino­quinolinium 3‐carboxy‐4‐hydroxy­benzene­sulfonate dihydrate, C9H9N2+·C7H5O6S−·2H2O, (III), and 2‐carboxy­quinolinium 3‐carboxy‐4‐hydroxy­benzene­sulfonate quinolinium‐2‐carboxylate, C10H8NO2+·C7H5O6S−·C10H7NO2, (IV), four proton‐transfer compounds of 5‐sulfosalicylic acid with bicyclic heteroaromatic Lewis bases, reveal in each the presence of variously hydrogen‐bonded polymers. In only one of these compounds, viz. (II), is the protonated quinolinium group involved in a direct primary N+—H⋯O(sulfonate) hydrogen‐bonding interaction, while in the other hydrates, viz. (I) and (III), the water mol­ecules participate in the primary intermediate interaction. The quinaldic acid (quinoline‐2‐carboxylic acid) adduct, (IV), exhibits cation–cation and anion–adduct hydrogen bonding but no direct formal heteromolecular interaction other than a number of weak cation–anion and cation–adduct π–π stacking associations. In all other compounds, secondary interactions give rise to network polymer structures.

Experimental and theoretical studies of the second- and third-order NLO properties of a semi-organic compound: 6-Aminoquinolinium iodide monohydrate

“…The cation is essentially planar with the ring atoms and the amino group having a RMS deviation of 0.0118Å. The geometry of the quinolinium fragment is similar to that found in other aminoquinolinium salt structures [51,52,53] There are five conventional hydrogen bonds in this structure (see Table 2 and Fig. 2).…”

Crystal Structure of a 1:1 Non-Proton-Transfer Hydrogen-Bonded Complex of Zwitterionic Quinaldic Acid with Chloranilic Acid Hydrate Adduct

“…5 The cation and zwitterionic QA species form a pseudo-dimer through a twisted cyclic H-bond duplex N-H·O association. This pseudo-dimer incorporates a cyclic association and two intramolecular N-H·Ocarboxyl associations, and is similar to that found in the zwitterionic parentacid, 6 the1:2LTA-QAadduct 4 andintheanalogous1:1:1 protonated QA-zwitterionic adduct compounds with 5-sulfosalicylicacid(5-SSA) 7 andDCPA. 3 However,inthe1:1 QA/DNSA 8 adduct, this dimer is not found.…”

Hydrogen Bonding in Proton-Transfer Compounds of 5-Sulfosalicylic Acid with a Series of Aliphatic Nitrogen Lewis Bases

“…The utility of 3-carboxy-4-hydroxybenzenesulfonic acid (5-sulfosalicylic acid, 5-SSA) for the formation of stable crystalline salts with nitrogen Lewis bases has been recognized for some time particularly those of the aromatic amines, making it a useful synthon for crystal engineering purposes [1][2][3][4]. In addition a number of the compounds of 5-SSA possess unusual conductivity properties [4] shared by the acid itself, which is sufficiently strong to protonate water [5,6].…”

“…The potential of 5-SSA as an anion or dianion in self-assembly processes can be attributed largely to the presence of the interactive sulfonate, carboxylic acid and phenolic functional groups which are capable of acting both as proton donors and acceptors in hydrogen-bonding interactions. We have prepared and crystallographically characterized a series of structures of these aromatic Lewis base salts, including those with the 4-X-substituted anilines (X = F, Cl, Br [7], CO 2 H [8]), 3-aminobenzoic acid [9], 3-methoxyaniline [10], benzylamine [11], the 2-X-substituted pyridines (X = NH 2 , OH) [12] and pyrimidine (X = NH 2 ) [12], the aromatic polyamines (2,6-diaminopyridine and 1,4-phenylenediamine) [13] and bicyclic heteroaromatic amines (quinoline, 8-aminoquinoline, 8-hydroxyquinoline and quinaldic acid) [3]. There have also been a large number of additional structures of aromatic amine salts of 5-SSA reported up until the present time, including those of simple monocyclic heteroaromatic amines [14][15][16][17][18][19][20][21][22][23][24], polycyclic heteroaromatic amines [25][26][27][28] and complex amines [29][30][31].…”

“…The aromatic and heteroaromatic Lewis base salts have additional potential for structure stabilization through cation-anion aromatic π-π ring interactions, although the incidence of this is limited to the structures of the salts of 5-SSA largely, but not exclusively with the heteroaromatic amines, e.g. the 2-Xsubstituted pyridines [12], pyridine-2,6-diamine [13] and quinoline-2-carboxylic acid [3]. However, in the crystallographic literature there are fewer structures of the aliphatic Lewis base salts of 5-SSA.…”