2003
DOI: 10.1071/ch02163
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Structure-Making with 3,5-Dinitrosalicylic Acid. II. The Proton-Transfer Compounds of 3,5-Dinitrosalicylic Acid with the Monocyclic Heteroaromatic Amines

Abstract: The crystal structures of the proton-transfer compounds of 3,5-dinitrosalicylic acid (dnsa) with a series of common monocyclic hetero-aromatic amines (pyridine, 4-cyanopyridine, pyridine-4-carboxylic acid, 2,6-diaminopyridine and 2-aminopyrimidine) have been determined and the hydrogen-bonding associations in each analyzed. The compounds are the adduct (C 5 H 6 N) + (dnsa) -

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Cited by 48 publications
(37 citation statements)
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“…This is also similar to the dnsa series where the maximum deviation from planarity for this torsion angle is 19.6 o in the compound with quinaldic acid [4] but is more typically <10 o .However, the torsion angle variation for the more associative nitro substituent at C3 in the set of dnsa compounds is much greater with a maximum value of 25.5 o in the compound with pyridine compound [3] This is considered as being due to the absence in 5-nsa of the second nitro group at C3. Because of this absence, the common proximal-group interactions involving carboxyl, phenol and nitro oxygen acceptors, which in dnsa has resulted in the structural characterization of 36 proton-transfer compounds, [1][2][3][4]16] cannot occur. As with the dnsa compounds there are, in addition, fewer extending interactions involving the 5-nitro oxygen acceptors while the nitro group itself shows a lesser tendency to become a more flexible proton acceptor through rotation of the oxygen atoms out of the plane of the parent ring.…”
Section: Conformational Features Of the 5-nsa Speciessupporting
confidence: 49%
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“…This is also similar to the dnsa series where the maximum deviation from planarity for this torsion angle is 19.6 o in the compound with quinaldic acid [4] but is more typically <10 o .However, the torsion angle variation for the more associative nitro substituent at C3 in the set of dnsa compounds is much greater with a maximum value of 25.5 o in the compound with pyridine compound [3] This is considered as being due to the absence in 5-nsa of the second nitro group at C3. Because of this absence, the common proximal-group interactions involving carboxyl, phenol and nitro oxygen acceptors, which in dnsa has resulted in the structural characterization of 36 proton-transfer compounds, [1][2][3][4]16] cannot occur. As with the dnsa compounds there are, in addition, fewer extending interactions involving the 5-nitro oxygen acceptors while the nitro group itself shows a lesser tendency to become a more flexible proton acceptor through rotation of the oxygen atoms out of the plane of the parent ring.…”
Section: Conformational Features Of the 5-nsa Speciessupporting
confidence: 49%
“…However, the quality of the crystalline proton-transfer products obtained with 5-nsa is poor by comparison so that the description of the modes of interaction of Lewis base cations with 5-nsa anions is negligible compared to those with dnsa where 36 have been crystallographically characterized. [1][2][3][4] The only reported proton-transfer structures of 5-nsa are with 3-amino-1H-1,2,4-triazole (3-at), [(3-at) + (5-nsa) -] [5] and with 8-aminoquinoline (8-aq), [(8-aq) + (5-nsa) -]. [6] We have also reported the preparation of the 1:1 proton-transfer compounds with 8-hydroxyquinoline [7] and creatinine [8] but poor crystal quality precluded their determination by X-ray methods.…”
Section: Introductionmentioning
confidence: 99%
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“…3,5-Dinitrosalicylic acid (2-hydroxy-3,5-dinitrobenzoic acid) is used to detect reducing substances in urine, for quantifying carbohydrate levels in blood and in assays of α-amylase. There are several crystal structure reports on 3,5-dinitrosalicylate with a variety of anions like 2-methoxyanilinium [1], 4-aminobenzenesulfonamide [2], 4-cyanopyridinium [3], ammonium [4], diethylammonium [5], 1-phenylethylaminium [6] and 3-(1H-imidazol-1-yl)propan-1-aminium [7] and some cases where 3,5-dinitrosalicylate is coordinated to copper(II) in a bidentate fashion [8,9] but no structure reports the tetraethylammonium salt. …”
Section: Discussionmentioning
confidence: 99%
“…At the present time a number of works devoted to the creation of polymers on the basis of cyanopyridines and their derivatives have been published [5,6].…”
Section: Introductionmentioning
confidence: 99%