Structural studies of solid state hydrogen bonding in adducts of some amine derivatives
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Date
2004-12
Authors
Suchada Chantrapromma
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Abstract
The nature of hydrogen bonding related to the acid-base properties in crystalline
phenolslbenzoic acids-amine adducts were investigated using single crystal X-ray
structure determination. Fourteen new crystal structures were determined and the results
showed that the nature of hydrogen bonding in crystalline phenolsfbenzoic acids-amine
ad ducts is solely governed by the acidity and is independent of the basicity of their
constituents. Steric effects may also play an important role in the formation of the solid
state hydrogen bonding networks.
Protonation occurs and organic salts are formed for adducts arising from strong
acids. For these adducts of strong acids, the roles of hydrogen donors and hydrogen
acceptors in hydrogen bonding have been reversed. The acidic component is the
acceptor and the basic component is the donor. In addition, a newly-discovered second
order temperature-dependent reversible ferroelastic phase transition which we named as
FAST (Fun-Anwar-Suchada Transition) occurs for three cases, namely,
hexamethylenetetraminium 2, 4-dinitropheno late monohydrate (HMTDNP],
hexamethylenetetraminium 3 ,5-dinitrobenzoate-3 ,5-dinitrobenzoic acid monohydrate
(HMT2DNBW] and quinuclidinium 2,4-dinitrophenolate [QNCDNP]. This newlydiscovered
ferroelastic transition, FAST, was explained theoretically using the
phenomenological theory of Landau. For other types of adducts, only ordinary adducts
were formed. The acidic component is the donor and the basic component is the
acceptor in the hydrogen bonding.
Four other related crown ether crystal structures were also determined.
Additionally, two of these crown ether crystal structures, namely, barium(II) 2,4-
dinitrophenolate-18-crown-6 [BaDNP-Crown] and a ternary complex of 18-crown-6-
3,5-dinitrobenzoic acid-water (1/212) [DNB-Crown], exhibit interesting temperaturedependent
variation of their unit cell parameters.
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Keywords
The nature of hydrogen bonding in crystalline phenolsfbenzoic acids-amine ad ducts , is solely governed by the acidity and is independent of the basicity of their constituents.