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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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.
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