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
Smith, Graham & Wermuth, Urs D. (2010) 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. Acta Crystallographica. Section C: Crystal Structure Communications, 66, o374-o380.
The structures of 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
C~6~H~16~N^+^ C~8~H~3~Cl~2~O~4~^-^ (I), diethylaminium
C~4~H~12~N^+^ C~8~H~3~Cl~2~O~4~^-^ (II), bis(n-butylaminium) 4,5-dichlorophthalate monohydrate
2(C~4~H~12~N^+^) C~8~H~2~Cl~2~O~4~^2-^ . H~2~O (III) and
bis(piperidinium) 4,5-dichlorophthalate monohydrate
2(C~5~H~12~N^+^) C~8~H~2~Cl~2~O~4~^2-^ . H~2~O (IV)have been determined at 200 K. All compounds have hydrogen-bonding associations giving in (I) discrete cation-anion units, 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 R2/1(4) N+-H...O,O' hydrogen-bonding association whereas in (II), one-dimensional chains are formed through linear N-H...O associations by both aminium H donors. In compounds (III) and (IV) the primary N-H...O linked cation-anion units are
extended into a two-dimensional sheet structure via amide N-H...O(carboxyl) and ...O(carbonyl) interactions.
In the 1:1 salts [(I) and (II)], the hydrogen 4,5-dichlorophthalate anions are essentially planar with short intramolecular carboxylic acid O-H...O(carboxyl) hydrogen bonds [O...O, 2.4223(14) and 2.388(2)A 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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|Item Type:||Journal Article|
|Keywords:||crystal structure, 4,5-dichlorophthalic acid, hydrogen bonding, Lewis base salts|
|Subjects:||Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > PHYSICAL CHEMISTRY (INCL. STRUCTURAL) (030600)|
|Divisions:||Past > Schools > Chemistry|
Past > QUT Faculties & Divisions > Faculty of Science and Technology
|Copyright Owner:||Copyright 2010 International Union of Crystallography|
|Deposited On:||25 Jun 2010 10:21|
|Last Modified:||01 Mar 2012 00:27|
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