Salts of maleic and fumaric acids with oxine: the role of isomeric acids in hydrogen-bonding patterns

Abstract

Both maleic and fumaric acid readily form adducts or complexes with other organic molecules. The 1:1 adduct formed by quinolin-8-ol (oxine) with maleic and fumaric acid are salts, namely 8-hydroxyquinolinium hydrogen maleate, C(9)H(8)NO(+).C(4)H(3)O(4)(-), (I), and 8-hydroxyquinolinium hydrogen fumarate, C(9)H(8)NO(+).C(4)H(3)O(4)(-), (II). The cations and anions of both salts are linked by ionic N(+)-H...O(-) hydrogen bonds. The maleate salt crystallizes in the space group P2(1)2(1)2(1), while the fumarate salt crystallizes in P\overline{1}. The maleic and fumaric acids in their complex forms exist as semimaleate and semifumarate ions (mono-ionized state), respectively. Classical N-H...O and O-H...O hydrogen bonds, together with short C-H...O contacts, generate an extensive hydrogen-bonding network. The crystal structures of the maleate and fumarate salts of oxine have been elucidated to study the importance of noncovalent interactions in the aggregation and interaction patterns of biological molecules. The structures of the salts of the Z and E isomers of butenedioic acid (maleic and fumaric acid, respectively) with quinolin-8-ol are compared.

ZandEisomers of butenedioic acid with 2-amino-1,3-thiazole: 2-amino-1,3-thiazolium hydrogen maleate and 2-amino-1,3-thiazolium hydrogen fumarate

“…The present study reports the structures of 2ATHM and 2ATHF, 1:1 organic salts of 2-amino-1,3-thiazole with the Z and E isomers of butenedioic acid, respectively. This work is a continuation of the study of the salts of the Z and E isomers of butenedioic acid with 8-hydroxyquinoline reported from our laboratory recently (Franklin & Balasubramanian, 2009). The crystal structure of the salt of 2-amino-1,3-thiazole with succinic acid has also been reported by us recently (Fun et al, 2009).…”

“…These D 2 2 (9) motifs are linked through an O-HÁ Á ÁO hydrogen bond (entry 7 in Table 3), forming a one-dimensional anionic chain extending along the [001] direction. A similar one-dimensional anionic chain is observed in most of the fumarate salts (Franklin & Balasubramanian, 2009;Bowes et al, 2003; Bü yü kgü ngö r et al, 2004). The cations are linked to these anionic chains through N-HÁ Á ÁO hydrogen bonds to form a ring motif of type R 4 6 (24).…”

“…This intramolecular hydrogen bond with an S(7) motif is a common occurrence in several salts of maleate (Alagar et al, 2001(Alagar et al, , 2002Rajagopal et al, 2001Rajagopal et al, , 2002. The corresponding intramolecular hydrogen bond with an S(5) motif is found in the semifumarate anion of 8-hydroxyquinolinium hydrogen fumarate (Franklin & Balasubramanian, 2009) but is not observed here in the semifumarate anions of 2ATHF. The two structures here differ, with intermolecular hydrogen-bonding interactions observed between the semifumarate anions in 2ATHF but not between the semimaleate anions in 2ATHM.…”

“…3 and 4, respectively. In 2ATHM, an intramolecular hydrogen bond between atoms O1 and O4 of the semimaleate anion is asymmetric and generates an S(7) motif (Bernstein et al, 1995), as observed in 8-hydroxyquinolinium hydrogen maleate (Franklin & Balasubramanian, 2009). This intramolecular hydrogen bond with an S(7) motif is a common occurrence in several salts of maleate (Alagar et al, 2001(Alagar et al, , 2002Rajagopal et al, 2001Rajagopal et al, , 2002.…”

NLO and NBO Analysis of Sarcosine‐Maleic Acid by Using HF and B3LYP Calculations

“…e crystal structure of a complex of sarcosine with maleic acid have already been reported [43]. Also, the bond lengths and angles for the sarcosine were taken from the work of Mostad and Natarajan [9] and Krishnakumar et al [44] and for the maleic acid were taken from Franklin and Balasubramanian [45] and Zhang et al [46]. O-H bond lengths (0.940 and 1.530 Å) in the maleic acid were taken from the work of Zhang et al [46].…”