Low-dimensional hydrogen-bonded structures in the 1:1 and 1:2 proton-transfer compounds of 4,5-dichlorophthalic acid with the aliphatic Lewis bases triethylamine, diethylamine, n-butylamine and piperidine

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Author(s)
Smith, Graham
Wermuth, Urs D
Griffith University Author(s)
Year published
2010
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The structures of the proton-transfer compounds of 4,5-dichlorophthalic acid (DCPA) with the aliphatic Lewis bases triethylamine, diethylamine, n-butylamine and piperidine, namely triethylaminium 2-carboxy-4,5-dichlorobenzoate, C6H16N+烸H3Cl2O4-, (I), diethylaminium 2-carboxy-4,5-dichlorobenzoate, C4H12N+烸H3Cl2O4-, (II), bis(butanaminium) 4,5-dichlorobenzene-1,2-dicarboxylate monohydrate, 2C4H12N+烸H2Cl2O42-爲O, (III), and bis(piperidinium) 4,5-dichlorobenzene-1,2-dicarboxylate monohydrate, 2C5H12N+烸H2Cl2O42-爲O, (IV), have been determined at 200 K. All compounds have hydrogen-bonding associations, giving discrete cation-anion ...
View more >The structures of the proton-transfer compounds of 4,5-dichlorophthalic acid (DCPA) with the aliphatic Lewis bases triethylamine, diethylamine, n-butylamine and piperidine, namely triethylaminium 2-carboxy-4,5-dichlorobenzoate, C6H16N+烸H3Cl2O4-, (I), diethylaminium 2-carboxy-4,5-dichlorobenzoate, C4H12N+烸H3Cl2O4-, (II), bis(butanaminium) 4,5-dichlorobenzene-1,2-dicarboxylate monohydrate, 2C4H12N+烸H2Cl2O42-爲O, (III), and bis(piperidinium) 4,5-dichlorobenzene-1,2-dicarboxylate monohydrate, 2C5H12N+烸H2Cl2O42-爲O, (IV), have been determined at 200 K. All compounds have hydrogen-bonding associations, giving discrete cation-anion units in (I) and linear chains in (II), while (III) and (IV) both have two-dimensional structures. In (I), a discrete cation-anion unit is formed through an asymmetric R12(4) N+-HO2 hydrogen-bonding association, whereas in (II), chains are formed through linear N-HO associations involving both aminium H-atom donors. In compounds (III) and (IV), the primary N-HO-linked cation-anion units are extended into a two-dimensional sheet structure via amide-carboxyl N-HO and amide-carbonyl N-HO interactions. In the 1:1 salts (I) and (II), the hydrogen 4,5-dichlorophthalate anions are essentially planar with short intramolecular carboxyl-carboxyl O-HO hydrogen bonds [OO = 2.4223 (14) and 2.388 (2) Ŭ respectively]. This work provides a further example of the uncommon zero-dimensional hydrogen-bonded DCPA-Lewis base salt and the one-dimensional chain structure type, while even with the hydrate structures of the 1:2 salts with the primary and secondary amines, the low dimensionality generally associated with 1:1 DCPA salts is also found.
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View more >The structures of the proton-transfer compounds of 4,5-dichlorophthalic acid (DCPA) with the aliphatic Lewis bases triethylamine, diethylamine, n-butylamine and piperidine, namely triethylaminium 2-carboxy-4,5-dichlorobenzoate, C6H16N+烸H3Cl2O4-, (I), diethylaminium 2-carboxy-4,5-dichlorobenzoate, C4H12N+烸H3Cl2O4-, (II), bis(butanaminium) 4,5-dichlorobenzene-1,2-dicarboxylate monohydrate, 2C4H12N+烸H2Cl2O42-爲O, (III), and bis(piperidinium) 4,5-dichlorobenzene-1,2-dicarboxylate monohydrate, 2C5H12N+烸H2Cl2O42-爲O, (IV), have been determined at 200 K. All compounds have hydrogen-bonding associations, giving discrete cation-anion units in (I) and linear chains in (II), while (III) and (IV) both have two-dimensional structures. In (I), a discrete cation-anion unit is formed through an asymmetric R12(4) N+-HO2 hydrogen-bonding association, whereas in (II), chains are formed through linear N-HO associations involving both aminium H-atom donors. In compounds (III) and (IV), the primary N-HO-linked cation-anion units are extended into a two-dimensional sheet structure via amide-carboxyl N-HO and amide-carbonyl N-HO interactions. In the 1:1 salts (I) and (II), the hydrogen 4,5-dichlorophthalate anions are essentially planar with short intramolecular carboxyl-carboxyl O-HO hydrogen bonds [OO = 2.4223 (14) and 2.388 (2) Ŭ respectively]. This work provides a further example of the uncommon zero-dimensional hydrogen-bonded DCPA-Lewis base salt and the one-dimensional chain structure type, while even with the hydrate structures of the 1:2 salts with the primary and secondary amines, the low dimensionality generally associated with 1:1 DCPA salts is also found.
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Journal Title
Acta Crystallographica. Section C: Crystal Structure Communications
Volume
66
Issue
7
Copyright Statement
© 2010 International Union of Crystallography. Published by Blackwell Publishing Ltd. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version.
Subject
Inorganic chemistry
Physical chemistry
Other chemical sciences